Pub Date : 2024-02-07DOI: 10.2174/0115701794279003240124113635
Zhijie Deng, Tao Tao, Jianzhong Yuan, Caichao Wan
: Cellulose nanocrystals (CNCs) have triggered considerable research interest in the last few years owing to their unique optical, biodegradation, and mechanical behavior. Herein, recent progress on the sensing application of photonic CNC films is summarized and discussed based on the analyses of the latest studies. We briefly introduce the three approaches for pre-paring CNCs: mechanical treatment, acid hydrolysis, and enzymatic hydrolysis, recapitulating their differences in preparation and properties. Then, when the aqueous suspension of cellu-lose nanocrystals (CNCs) reaches a specific concentration, it will self-assemble to form a left-handed nematic liquid crystal structure, and this structure can be maintained in films after water evaporation, which has strong photonic crystal properties. The periodic layered structure in the film interferes and diffracts with light, showing a rainbow color. Photonic CNC com-posites that combine CNCs and functional materials have good properties and broad prospects. Finally, we highlight the advanced applications of photonic CNC films, including mechanical sensing, thermal sensing, and humidity sensing. The prospects and ongoing challenges of pho-tonic CNC films were summarized.
{"title":"Recent Progress on Photonic Cellulose Nanocrystal Films for Sensing Applications","authors":"Zhijie Deng, Tao Tao, Jianzhong Yuan, Caichao Wan","doi":"10.2174/0115701794279003240124113635","DOIUrl":"https://doi.org/10.2174/0115701794279003240124113635","url":null,"abstract":": Cellulose nanocrystals (CNCs) have triggered considerable research interest in the last few years owing to their unique optical, biodegradation, and mechanical behavior. Herein, recent progress on the sensing application of photonic CNC films is summarized and discussed based on the analyses of the latest studies. We briefly introduce the three approaches for pre-paring CNCs: mechanical treatment, acid hydrolysis, and enzymatic hydrolysis, recapitulating their differences in preparation and properties. Then, when the aqueous suspension of cellu-lose nanocrystals (CNCs) reaches a specific concentration, it will self-assemble to form a left-handed nematic liquid crystal structure, and this structure can be maintained in films after water evaporation, which has strong photonic crystal properties. The periodic layered structure in the film interferes and diffracts with light, showing a rainbow color. Photonic CNC com-posites that combine CNCs and functional materials have good properties and broad prospects. Finally, we highlight the advanced applications of photonic CNC films, including mechanical sensing, thermal sensing, and humidity sensing. The prospects and ongoing challenges of pho-tonic CNC films were summarized.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"88 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139762652","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-02-07DOI: 10.2174/0115701794274892231229110318
Mehdi Khoshkharam, Mohamad Hesam Shahrajabian, Wenli Sun
: Allelopathy is related to the positive or negative impacts on one type of plant of a chemical produced by another type of plant, such as weeds, and different kinds of chemicals are hydroxamic acids, phenolics, and short-chain fatty acids. The potential allelopathic impacts of weeds are directly associated with the plant species used, as well as the concentration of the aqueous extract available in the environment. The present research has made an attempt to find and identify the allelopathic effects of aquatic extracts from dry seeds and shoots of mallow (Malva sylvestris L.) on germination, seedling growth, and progress of three cultivars of maize. Maize seeds (Zea mays L.) were obtained as seed material; three maize seed cultivars were KSC 704 (cultivar 1), KSC 500 (cultivar 2), and KSC 302 (cultivar 3), respectively. The aqueous ex-tracts of mallow shoots and seeds, in concentrations of 1, 3, and 5%, were made from the crum-bled and dried above-ground plant sections. The influence of plant dosage was significant on the coefficient of the rate of germination (CRG), seedling vigour index (SVI), total germination (T50), mean germination time (MGT), germination energy (GE), germination index (GI), inhibi-tion percentage (IP), fresh mass, dry mass, relative water content (RWC), and total water content (TWC). Different plant parts had a meaningful influence on SVI, GI, MGT, CRG, GE, and IP. The impacts of the cultivar on T50, IP, RWC, fresh mass, dry mass, and TWC were significant. Together with the increase in the concentration of allelopathic components, a decline in the ger-mination activity of all tested maize cultivars was found. The highest SVI was associated with control treatment, followed by 1% and 3% of plant dosages. KSC 704 obtained the maximum CRG and GE, and the minimum one was related to KSC 500. 3% of plant dosage has obtained the highest value of CRG and GE. The maximum and the minimum T50 were related to KSC 302 and KSC 704, respectively. The lowest values of GI and MGT were related to KSC 500, and the maximum values were related to KSC 704. While the maximum IP, RWC, fresh mass, dry mass, and TWC were related to KSC 704, the lowest values were achieved for KSC 500. The RWC was the highest for seedlings grown on the 5% extract. The information provided in this article can be helpful in the conditions of the threat of maize seedlings with the mass appearance of mallow.
{"title":"Changes in Germination Parameters, Growth and Development of Three Cultivars of Corn Seedlings under Various Aqueous Extracts of Mallow","authors":"Mehdi Khoshkharam, Mohamad Hesam Shahrajabian, Wenli Sun","doi":"10.2174/0115701794274892231229110318","DOIUrl":"https://doi.org/10.2174/0115701794274892231229110318","url":null,"abstract":": Allelopathy is related to the positive or negative impacts on one type of plant of a chemical produced by another type of plant, such as weeds, and different kinds of chemicals are hydroxamic acids, phenolics, and short-chain fatty acids. The potential allelopathic impacts of weeds are directly associated with the plant species used, as well as the concentration of the aqueous extract available in the environment. The present research has made an attempt to find and identify the allelopathic effects of aquatic extracts from dry seeds and shoots of mallow (Malva sylvestris L.) on germination, seedling growth, and progress of three cultivars of maize. Maize seeds (Zea mays L.) were obtained as seed material; three maize seed cultivars were KSC 704 (cultivar 1), KSC 500 (cultivar 2), and KSC 302 (cultivar 3), respectively. The aqueous ex-tracts of mallow shoots and seeds, in concentrations of 1, 3, and 5%, were made from the crum-bled and dried above-ground plant sections. The influence of plant dosage was significant on the coefficient of the rate of germination (CRG), seedling vigour index (SVI), total germination (T50), mean germination time (MGT), germination energy (GE), germination index (GI), inhibi-tion percentage (IP), fresh mass, dry mass, relative water content (RWC), and total water content (TWC). Different plant parts had a meaningful influence on SVI, GI, MGT, CRG, GE, and IP. The impacts of the cultivar on T50, IP, RWC, fresh mass, dry mass, and TWC were significant. Together with the increase in the concentration of allelopathic components, a decline in the ger-mination activity of all tested maize cultivars was found. The highest SVI was associated with control treatment, followed by 1% and 3% of plant dosages. KSC 704 obtained the maximum CRG and GE, and the minimum one was related to KSC 500. 3% of plant dosage has obtained the highest value of CRG and GE. The maximum and the minimum T50 were related to KSC 302 and KSC 704, respectively. The lowest values of GI and MGT were related to KSC 500, and the maximum values were related to KSC 704. While the maximum IP, RWC, fresh mass, dry mass, and TWC were related to KSC 704, the lowest values were achieved for KSC 500. The RWC was the highest for seedlings grown on the 5% extract. The information provided in this article can be helpful in the conditions of the threat of maize seedlings with the mass appearance of mallow.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"11 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139763135","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Background: One of the most researched issues is the elimination of uremic toxins from the human body. These toxins can build up and lead to catastrophic issues including renal failure. To get rid of them, absorbents like activated carbon, zeolites, and other minerals are frequently utilized. Methods: Mesoporous silica nanoparticles functionalized with (3-Aminopropyl) triethox-ysilane (APTES) linker (MSN-NH2) and mesoporous silica nanoparticles grafted with molec-ularly imprinted polymers (MSN-MIP) from the previous study were examined in this study to determine how well they absorbed urea, creatinine, and uric acid in a simulated intestinal serum. Results: MSN-MIP's large surface area (879.12 (m2/g)) and volume of pores (0.8475 (cm3/g)) made removal results that were satisfactory in the simulated serum. Additionally, MSN-MIP demonstrated a high urea adsorption capacity (qm = 1836.45 mg/g). Creatinine (qm = 1529.5 mg/g) and uric acid (qm = 1210.6 mg/g) were absorbed via NH-MSN2, which demonstrated a noticeable potential for absorption. The results of cell viability test for the first 72 hours, showed that the use of these absorbents in hemodialysis systems is acceptable. Conclusion: Synthesized adsorbents can be utilized in the hemodialysis system since the results of the cell viability test also showed that the percentage of cell viability was extremely high up to 72 hours.
{"title":"Uremic Toxins Elimination from Simulated Intestinal Serum with Mesopo-rous Silica Nanoparticles Coupled with Molecularly Imprinted Polymers and Amino Linker","authors":"Leila Nazmi Miardan, Ebrahim Rezaii, Mehrdad Mahkam, Hamid Tayebi Khosroshahi","doi":"10.2174/0115701794282603240115112013","DOIUrl":"https://doi.org/10.2174/0115701794282603240115112013","url":null,"abstract":"Background: One of the most researched issues is the elimination of uremic toxins from the human body. These toxins can build up and lead to catastrophic issues including renal failure. To get rid of them, absorbents like activated carbon, zeolites, and other minerals are frequently utilized. Methods: Mesoporous silica nanoparticles functionalized with (3-Aminopropyl) triethox-ysilane (APTES) linker (MSN-NH2) and mesoporous silica nanoparticles grafted with molec-ularly imprinted polymers (MSN-MIP) from the previous study were examined in this study to determine how well they absorbed urea, creatinine, and uric acid in a simulated intestinal serum. Results: MSN-MIP's large surface area (879.12 (m2/g)) and volume of pores (0.8475 (cm3/g)) made removal results that were satisfactory in the simulated serum. Additionally, MSN-MIP demonstrated a high urea adsorption capacity (qm = 1836.45 mg/g). Creatinine (qm = 1529.5 mg/g) and uric acid (qm = 1210.6 mg/g) were absorbed via NH-MSN2, which demonstrated a noticeable potential for absorption. The results of cell viability test for the first 72 hours, showed that the use of these absorbents in hemodialysis systems is acceptable. Conclusion: Synthesized adsorbents can be utilized in the hemodialysis system since the results of the cell viability test also showed that the percentage of cell viability was extremely high up to 72 hours.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"37 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139762774","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Aim and Objzectives: There are different approaches to the synthesis of benzimidazole. In this article, five new benzimidazole derivatives, BMPO, Me-BMPO, Di-MeBMPO, F-BMPO and Cl-BMPO where (BMPO=3-[(1H)-benzo[d]imidazol-2-yl]pyridin-2(1H)-one), have been prepared. Another study was carried out on luminescence properties and their potential applica-tions for the detection of transition metal ions. Materials and Methods: From the one-pot synthesis approach, all the derivatives of the benzim-idazole compounds were obtained. The compounds were characterized using HRMS, 1HNMR, 13CNMR, and X-ray crystallography. Herein, a mechanism has been deciphered by predicting the release of HCl(g). Results: All compounds showed a strong deep blue emission when dissolved in dimethylacetamide (DMA), with emission wavelengths at 423, 428, 435, 423, and 421 nm, and half-times of 3.64, 2.77, 2, 19, 3.42 and 3.52 ns, respectively. In addition, their emission quantum yields were deter-mined to be 72, 50, 42, 73 and 80%. Conclusion: Five new benzimidazole derivatives, BMPO, Me-BMPO, Di-MeBIPO, F-BIPO, and Cl-BIPO, have been successfully synthesized by the one-pot synthesis method, and their struc-tures are characterized and confirmed. The compounds exhibited exceptional luminescence by emitting a strong blue light in DMA with high fluorescence quantum yields between 42~80%.
{"title":"One Pot Synthesis of New Benzimidazole Derivatives with Exceptionally High Luminescence Quantum Efficiency","authors":"Abraham Mensah, Xin-Ye Liu, Bing-Xiang Hu, Ennin Vendish Kweku, Fang-Ming Wang, Li-Zhuang Chen, Shao-Jun Zheng","doi":"10.2174/0115701794271985231219070212","DOIUrl":"https://doi.org/10.2174/0115701794271985231219070212","url":null,"abstract":"Aim and Objzectives: There are different approaches to the synthesis of benzimidazole. In this article, five new benzimidazole derivatives, BMPO, Me-BMPO, Di-MeBMPO, F-BMPO and Cl-BMPO where (BMPO=3-[(1H)-benzo[d]imidazol-2-yl]pyridin-2(1H)-one), have been prepared. Another study was carried out on luminescence properties and their potential applica-tions for the detection of transition metal ions. Materials and Methods: From the one-pot synthesis approach, all the derivatives of the benzim-idazole compounds were obtained. The compounds were characterized using HRMS, 1HNMR, 13CNMR, and X-ray crystallography. Herein, a mechanism has been deciphered by predicting the release of HCl(g). Results: All compounds showed a strong deep blue emission when dissolved in dimethylacetamide (DMA), with emission wavelengths at 423, 428, 435, 423, and 421 nm, and half-times of 3.64, 2.77, 2, 19, 3.42 and 3.52 ns, respectively. In addition, their emission quantum yields were deter-mined to be 72, 50, 42, 73 and 80%. Conclusion: Five new benzimidazole derivatives, BMPO, Me-BMPO, Di-MeBIPO, F-BIPO, and Cl-BIPO, have been successfully synthesized by the one-pot synthesis method, and their struc-tures are characterized and confirmed. The compounds exhibited exceptional luminescence by emitting a strong blue light in DMA with high fluorescence quantum yields between 42~80%.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"87 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139517908","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-17DOI: 10.2174/0115701794282903231228055914
Hind M. A. Yahya, Jalal A. Zahra, Salim S. Sabri, Mustafa M. El-Abadelah, Sanaa Bardaweel
Background: Hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, undergoes a reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. background: The hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, underwent reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Introduction: A novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates (7a-h) incorporating N-piperazines or related congeners was synthesized via interaction of the hy-drazonoyl chloride (6), accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carbox-ylate, with the appropriate sec-cyclic amine. These new compounds were characterized by 1H-NMR, 13C-NMR, and HRMS spectral data and screened for their anticancer activities. Aims: This study aimed at the synthesis of novel N1-( 4-oxoquinolin-5-yl)amidrazone carboxylate derivatives and investigated their potential as anticancer agents. Objective: The reaction of hydrazonoyl chloride with the appropriate sec-cyclic amine was applied to synthesize a novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5- yl)amidrazone carboxylates that incorporate N piperazines. Methods: A direct reaction of piperazines and related sec-cyclic amines with N-(4-oxoquinolin-5-yl)nitrile imine (1,3-dipole) was carried out for 8-10 h. conclusion: A novel set N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones were successfully synthesized. Several of these compounds showed moderate activity against three breast cancer cell lines (MCF-7, T47D, and MDA-MB-231) with IC50 values in the range =18-78µM compared to Doxorubicin Results: The 1,3-dipole, generated in situ from its hydrazonoyl chloride precursor in the presence of trimethylamine, is suitable for the facile synthesis of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Conclusion: This study led to the successful synthesis of novel N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones. All the examined compounds showed moderate activity with reasonable IC50 values in the micromolar range compared to Doxorubicin.
{"title":"Synthesis and Antitumor Activity of Some New N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones","authors":"Hind M. A. Yahya, Jalal A. Zahra, Salim S. Sabri, Mustafa M. El-Abadelah, Sanaa Bardaweel","doi":"10.2174/0115701794282903231228055914","DOIUrl":"https://doi.org/10.2174/0115701794282903231228055914","url":null,"abstract":"Background: Hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, undergoes a reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. background: The hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, underwent reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Introduction: A novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates (7a-h) incorporating N-piperazines or related congeners was synthesized via interaction of the hy-drazonoyl chloride (6), accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carbox-ylate, with the appropriate sec-cyclic amine. These new compounds were characterized by 1H-NMR, 13C-NMR, and HRMS spectral data and screened for their anticancer activities. Aims: This study aimed at the synthesis of novel N1-( 4-oxoquinolin-5-yl)amidrazone carboxylate derivatives and investigated their potential as anticancer agents. Objective: The reaction of hydrazonoyl chloride with the appropriate sec-cyclic amine was applied to synthesize a novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5- yl)amidrazone carboxylates that incorporate N piperazines. Methods: A direct reaction of piperazines and related sec-cyclic amines with N-(4-oxoquinolin-5-yl)nitrile imine (1,3-dipole) was carried out for 8-10 h. conclusion: A novel set N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones were successfully synthesized. Several of these compounds showed moderate activity against three breast cancer cell lines (MCF-7, T47D, and MDA-MB-231) with IC50 values in the range =18-78µM compared to Doxorubicin Results: The 1,3-dipole, generated in situ from its hydrazonoyl chloride precursor in the presence of trimethylamine, is suitable for the facile synthesis of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Conclusion: This study led to the successful synthesis of novel N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones. All the examined compounds showed moderate activity with reasonable IC50 values in the micromolar range compared to Doxorubicin.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"42 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139498437","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The [4+2] Diels-Alder cycloaddition has been widely used for the synthesis of six-mem-ber scaffolds. In recent years, there have been significant developments in this area, including the discovery and design of novel dienes and dienophiles with improved reactivity and selectivity. These new building blocks can be used to develop diverse molecular structures with functional group compatibility. Additionally, there is the use of catalytic systems and metal-mediated reactions to enable asymmetric [4+2] cycloadditions, resulting in enantiomerically enriched products. Over-all, recent studies related to [4+2] Diels-Alder cycloaddition using numerous dienes, dienophiles, and catalysts in different reaction conditions have significantly improved the efficiency, selectivity, and versatility of the reaction, making it an increasingly important tool in the synthesis of complex organic molecules as presented in this review. These advancements offer exciting possibilities for the development of new methods and reagents for the construction of six-membered rings and the synthesis of bioactive compounds.
{"title":"A Brief Review on Recent Developments in Diels-Alder Reactions.","authors":"Manish Chaudhary, Shareef Shaik, Muskan Magan, Sharwan Hudda, Mukta Gupta, Gurvinder Singh, Pankaj Wadhwa","doi":"10.2174/0115701794262102231214074336","DOIUrl":"https://doi.org/10.2174/0115701794262102231214074336","url":null,"abstract":"<p><p>The [4+2] Diels-Alder cycloaddition has been widely used for the synthesis of six-mem-ber scaffolds. In recent years, there have been significant developments in this area, including the discovery and design of novel dienes and dienophiles with improved reactivity and selectivity. These new building blocks can be used to develop diverse molecular structures with functional group compatibility. Additionally, there is the use of catalytic systems and metal-mediated reactions to enable asymmetric [4+2] cycloadditions, resulting in enantiomerically enriched products. Over-all, recent studies related to [4+2] Diels-Alder cycloaddition using numerous dienes, dienophiles, and catalysts in different reaction conditions have significantly improved the efficiency, selectivity, and versatility of the reaction, making it an increasingly important tool in the synthesis of complex organic molecules as presented in this review. These advancements offer exciting possibilities for the development of new methods and reagents for the construction of six-membered rings and the synthesis of bioactive compounds.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139680878","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-13DOI: 10.2174/0115701794268766231108110816
Suzaimi Johari, Mohd Rafie Johan, Nader Ghaffari Khaligh
Aim and Objective: The establishment of a green and sustainable Knoevenagel con-densation reaction in organic chemistry is still crucial. This work aimed to provide a newly de-veloped metal-free and halogen-free catalytic methodology for the synthesis of CS and (het-ero-)arylidene malononitriles in the laboratory and industrial scale. The Knoevenagel condensa-tion reaction of various carbonyl groups with malononitrile was investigated in ethanol, an eco-friendly medium, in the presence of seven nitrogen-based organocatalysts. Materials and Methods: A comparative study was conducted using two as-obtained and four commercially available nitrogen-based organocatalysts in Knoevenagel condensation reactions. The synthesis of CS gas (2-chlorobenzylidene malononitrile) using a closed catalytic system was optimized based on their efficiency and greener approach. Results: The conversion of 100% and excellent yields were obtained in a short time. The products could be crystallized directly from the reaction mixture. After separating pure products, the resi-due solution was employed directly in the next run without any concentration, activation, purification, or separation. Furthermore, the synthesis of 2-chlorobenzylidenemahmonitrile (CS) was carried out on a large scale using imidazole as a selected nitrogen-based catalyst, afforded crys-talline products with 95±2% yield in five consecutive runs. Conclusion: Energy efficiency, cost saving, greener conditions, using only 5 mol% of organo-catalyst, high recyclability of catalyst, prevention of waste, recycling extractant by a rotary evaporator for non-crystallized products, demonstrated the potential commercial production of CS using imidazole in ethanol as an efficient and highly recyclable catalytic system
{"title":"Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy","authors":"Suzaimi Johari, Mohd Rafie Johan, Nader Ghaffari Khaligh","doi":"10.2174/0115701794268766231108110816","DOIUrl":"https://doi.org/10.2174/0115701794268766231108110816","url":null,"abstract":"Aim and Objective: The establishment of a green and sustainable Knoevenagel con-densation reaction in organic chemistry is still crucial. This work aimed to provide a newly de-veloped metal-free and halogen-free catalytic methodology for the synthesis of CS and (het-ero-)arylidene malononitriles in the laboratory and industrial scale. The Knoevenagel condensa-tion reaction of various carbonyl groups with malononitrile was investigated in ethanol, an eco-friendly medium, in the presence of seven nitrogen-based organocatalysts. Materials and Methods: A comparative study was conducted using two as-obtained and four commercially available nitrogen-based organocatalysts in Knoevenagel condensation reactions. The synthesis of CS gas (2-chlorobenzylidene malononitrile) using a closed catalytic system was optimized based on their efficiency and greener approach. Results: The conversion of 100% and excellent yields were obtained in a short time. The products could be crystallized directly from the reaction mixture. After separating pure products, the resi-due solution was employed directly in the next run without any concentration, activation, purification, or separation. Furthermore, the synthesis of 2-chlorobenzylidenemahmonitrile (CS) was carried out on a large scale using imidazole as a selected nitrogen-based catalyst, afforded crys-talline products with 95±2% yield in five consecutive runs. Conclusion: Energy efficiency, cost saving, greener conditions, using only 5 mol% of organo-catalyst, high recyclability of catalyst, prevention of waste, recycling extractant by a rotary evaporator for non-crystallized products, demonstrated the potential commercial production of CS using imidazole in ethanol as an efficient and highly recyclable catalytic system","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"65 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139465143","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-12DOI: 10.2174/0115701794269765231204064930
Paola Cuervo-Prado, Fabián Orozco-López, Christian Becerra-Rivas, Diego Leon-Vargas, John Lozano-Oviedo, Justo Cobo
Background: Pyrazolopyridines are interesting fused heterocyclic pharmacophores that combine pyrazole and pyridine; two privileged nuclei extensively studied and with a wide range of applications. They can be obtained by a broad variety of synthetic methods among which multicomponent reactions have gained importance, especially from 5-aminopyrazoles and dielectrophilic reagents. However, the search for new approaches more in tune with sustainable chemistry and the use of unconventional heating in three-component synthesis are open and highly relevant study fields. Methods: A novel, practical and efficient three-component synthesis of cycloalkane-fused pyra-zolo[4,3-e]pyridines was developed through a tandem reaction of 5-aminopyrazoles, cyclic ke-tones and electron-rich olefins, using microwave induction in perfluorinated solvent and iodine as catalyst. objective: To apply the principles of sustainable chemistry through a microwave-induced synthesis in perfluorinated solvent to obtain novel cycloalkane-fused pyrazolo[4,3-e]pyridines, taking advantage of the versatility of electron-rich olefins in iodine-catalyzed cascade heterocyclizations. Results: The microwave-induced three-component approach applied in this work promoted the construction of 10 new pyrazolopyridines with high speed and excellent control of regioselec-tivity, favoring the linear product with good yields; where the versatility of electron-rich olefins in iodine-catalyzed cascade heterocyclizations, granted the additional benefit of easy isolation and the possibility to reuse the fluorous phase. Conclusions: Although pyrazolopyridines have been synthetically explored because of their structural and biological properties, most of the reported synthetic methods use common or even toxic organic solvents and conventional heating or multi-step processes. In contrast, this study applied a multicomponent methodology in a single step by microwave induction and with the versatility provided in this case by the use of perfluorinated solvent, which allowed easy isolation of the final product and recovery of the fluorous phase.
{"title":"Regioselective Synthesis of Cycloalkane-fused pyrazolo[4,3-e]pyridines through Tandem Reaction of 5-aminopyrazoles, Cyclic Ketones and Electron-rich Olefins","authors":"Paola Cuervo-Prado, Fabián Orozco-López, Christian Becerra-Rivas, Diego Leon-Vargas, John Lozano-Oviedo, Justo Cobo","doi":"10.2174/0115701794269765231204064930","DOIUrl":"https://doi.org/10.2174/0115701794269765231204064930","url":null,"abstract":"Background: Pyrazolopyridines are interesting fused heterocyclic pharmacophores that combine pyrazole and pyridine; two privileged nuclei extensively studied and with a wide range of applications. They can be obtained by a broad variety of synthetic methods among which multicomponent reactions have gained importance, especially from 5-aminopyrazoles and dielectrophilic reagents. However, the search for new approaches more in tune with sustainable chemistry and the use of unconventional heating in three-component synthesis are open and highly relevant study fields. Methods: A novel, practical and efficient three-component synthesis of cycloalkane-fused pyra-zolo[4,3-e]pyridines was developed through a tandem reaction of 5-aminopyrazoles, cyclic ke-tones and electron-rich olefins, using microwave induction in perfluorinated solvent and iodine as catalyst. objective: To apply the principles of sustainable chemistry through a microwave-induced synthesis in perfluorinated solvent to obtain novel cycloalkane-fused pyrazolo[4,3-e]pyridines, taking advantage of the versatility of electron-rich olefins in iodine-catalyzed cascade heterocyclizations. Results: The microwave-induced three-component approach applied in this work promoted the construction of 10 new pyrazolopyridines with high speed and excellent control of regioselec-tivity, favoring the linear product with good yields; where the versatility of electron-rich olefins in iodine-catalyzed cascade heterocyclizations, granted the additional benefit of easy isolation and the possibility to reuse the fluorous phase. Conclusions: Although pyrazolopyridines have been synthetically explored because of their structural and biological properties, most of the reported synthetic methods use common or even toxic organic solvents and conventional heating or multi-step processes. In contrast, this study applied a multicomponent methodology in a single step by microwave induction and with the versatility provided in this case by the use of perfluorinated solvent, which allowed easy isolation of the final product and recovery of the fluorous phase.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"94 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139465209","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: This review covers the literature information on the chemistry of hydrazonoyl halides with different substrates to give heterocyclic compounds. From the foregoing survey, it seems this provides a useful and convenient strategy for the synthesis of numerous heterocyclic derivatives. The subject of such reactions is still ongoing and undoubtedly will provide new fused functionalized compounds of both industrial and biological interest. A literature survey revealed that a great deal of interest has been focused on the synthesis of functionalized heterocyclic compounds due to their wide range of biological activities, such as contact dermatitis, anthelmintic, antiviral, antimicrobial, herbicidal, and anti-cancer. On the other hand, hydrazonoyl halides are interesting synthons for valuable bioactive heterocyclic compounds. The reaction of hydrazonoyl halides with various types of substrates gave a huge number of different heterocyclic systems. In this review, we collected all reactions of hydrazonoyl halides with different moieties and classified them as aryl diazo of monoheterocycles, aryldiazo of 5,5-bis-heterocycles, aryldiazo of 5,6-bis-heterocycles, aryldiazo of 6,6-bis-heterocycles, aryldiazo of 5,5,6-tri-heterocycles, aryldiazo of 5,6,6-tri-heterocycles, aryldiazo of 6,6,6-tri-heterocycles, hetero annulation of bisheterocycles, hetero annulation of tri-heterocycles, hetero-annulation of tetra-heterocycles, synthesis of spiro-heterocycles, heterocyclic ring transformations, and 1,3-dipolar cycloaddition reactions catalyzed by transition metals using hydrazonoyl halides as substrates. Most reaction types have been successfully applied and used in the production of biologically active compounds. The aim of the present survey is to consider in the reader the opportunity interactions and biological activities of hydrazonoyl halides. The information of several artificial paths and varied physics-chemical factors of such heterocycles made a special consideration of chemists in different fields to yield a combinatorial library and carry out thorough efforts in the search for hydrazonoyl halides
{"title":"Reactions and Biological Activities of Hydrazonoyl Halides","authors":"Munirah Alarbash, Yasir Al-Faiyz, Jeffery Wiggins, Abdelwahed Sayed","doi":"10.2174/0115701794268313231127110713","DOIUrl":"https://doi.org/10.2174/0115701794268313231127110713","url":null,"abstract":": This review covers the literature information on the chemistry of hydrazonoyl halides with different substrates to give heterocyclic compounds. From the foregoing survey, it seems this provides a useful and convenient strategy for the synthesis of numerous heterocyclic derivatives. The subject of such reactions is still ongoing and undoubtedly will provide new fused functionalized compounds of both industrial and biological interest. A literature survey revealed that a great deal of interest has been focused on the synthesis of functionalized heterocyclic compounds due to their wide range of biological activities, such as contact dermatitis, anthelmintic, antiviral, antimicrobial, herbicidal, and anti-cancer. On the other hand, hydrazonoyl halides are interesting synthons for valuable bioactive heterocyclic compounds. The reaction of hydrazonoyl halides with various types of substrates gave a huge number of different heterocyclic systems. In this review, we collected all reactions of hydrazonoyl halides with different moieties and classified them as aryl diazo of monoheterocycles, aryldiazo of 5,5-bis-heterocycles, aryldiazo of 5,6-bis-heterocycles, aryldiazo of 6,6-bis-heterocycles, aryldiazo of 5,5,6-tri-heterocycles, aryldiazo of 5,6,6-tri-heterocycles, aryldiazo of 6,6,6-tri-heterocycles, hetero annulation of bisheterocycles, hetero annulation of tri-heterocycles, hetero-annulation of tetra-heterocycles, synthesis of spiro-heterocycles, heterocyclic ring transformations, and 1,3-dipolar cycloaddition reactions catalyzed by transition metals using hydrazonoyl halides as substrates. Most reaction types have been successfully applied and used in the production of biologically active compounds. The aim of the present survey is to consider in the reader the opportunity interactions and biological activities of hydrazonoyl halides. The information of several artificial paths and varied physics-chemical factors of such heterocycles made a special consideration of chemists in different fields to yield a combinatorial library and carry out thorough efforts in the search for hydrazonoyl halides","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"59 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139465195","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: Allenamides are special allenes, and the unique reactivity, selectivity (both stereoselective and regionally selective) and stability of allenamides have been widely studied. In this review, the development of the free radical transformation of allenamides over the last few years will be summarized. This review discusses in detail in three parts: intermolecular radical addition to C- X (X = N, S, O, Se) bonds, metal salt mediated cyclization of allenamides, and photocatalytic cyclization of allenamides. In addition, reasonable details of the mechanisms are provided for the vast majority of these transformations.
{"title":"Recent progress in free radical transformations of allenamides","authors":"Yongchun Liu, Zimin Wang, Rui Li, Yinhai Yao, Zhichuan Shi, Qin Sun, Guowei Deng","doi":"10.2174/0115701794269961231027054854","DOIUrl":"https://doi.org/10.2174/0115701794269961231027054854","url":null,"abstract":": Allenamides are special allenes, and the unique reactivity, selectivity (both stereoselective and regionally selective) and stability of allenamides have been widely studied. In this review, the development of the free radical transformation of allenamides over the last few years will be summarized. This review discusses in detail in three parts: intermolecular radical addition to C- X (X = N, S, O, Se) bonds, metal salt mediated cyclization of allenamides, and photocatalytic cyclization of allenamides. In addition, reasonable details of the mechanisms are provided for the vast majority of these transformations.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"51 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139103412","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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