Pub Date : 2024-09-10DOI: 10.2174/0113852728322595240819045039
Manijeh Nematpour
: In this study, functionalized 2-(trichloromethyl)-1H-benzo[d]imidazole derivative with good yields was synthesized using a copper-catalyzed N-arylation reaction of 2-iodoaniline and trichloroacetonitrile. This reaction was performed by employing the catalytic value of copper (I) and 1,10-phenanthroline as the ligand in tetrahydrofuran solvent at 23°C. In the following, the reaction of the final product with phenylacetylene and sodium azide (Huisgen reaction) using the copper catalyst in water solvent at 23°C led to the synthesis of new (1,2,3-triazol)-1H-benzo[d]imidazole derivatives with the principles of green chemistry and suitable efficiency. The availability of raw materials and suitable catalysts, mild reaction conditions, and easy purification are among the advantages of this method for the synthesis of various multi-substituted benzo[d]imidazole and 1,2,3-triazole derivatives.
{"title":"A New Route for the Synthesis of Trichloromethyl-1H-Benzo[d]imidazole and (1,2,3- Triazol)-1H-Benzo[d]imidazole Derivatives via Copper-Catalyzed N-Arylation and Huisgen Reactions","authors":"Manijeh Nematpour","doi":"10.2174/0113852728322595240819045039","DOIUrl":"https://doi.org/10.2174/0113852728322595240819045039","url":null,"abstract":": In this study, functionalized 2-(trichloromethyl)-1H-benzo[d]imidazole derivative with good yields was synthesized using a copper-catalyzed N-arylation reaction of 2-iodoaniline and trichloroacetonitrile. This reaction was performed by employing the catalytic value of copper (I) and 1,10-phenanthroline as the ligand in tetrahydrofuran solvent at 23°C. In the following, the reaction of the final product with phenylacetylene and sodium azide (Huisgen reaction) using the copper catalyst in water solvent at 23°C led to the synthesis of new (1,2,3-triazol)-1H-benzo[d]imidazole derivatives with the principles of green chemistry and suitable efficiency. The availability of raw materials and suitable catalysts, mild reaction conditions, and easy purification are among the advantages of this method for the synthesis of various multi-substituted benzo[d]imidazole and 1,2,3-triazole derivatives.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214509","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-10DOI: 10.2174/0113852728323915240816093254
Santanu Chakravorty
: Palladium-catalyzed reactions are widely used for creating carbon-carbon and carbon-heteroatom bonds, with the Heck reaction being particularly valuable for forming rings of various sizes, including mediumsized rings. Recent reports have shown the synthetic potential of intramolecular Heck reactions for assembling rings of seven or more members. While the regioselectivity of this cyclization is often unpredictable in the absence of directing groups, the reductive Heck cyclization strategy can help minimize this issue. Nickel catalysts are also valuable due to their abundance and environmentally friendly nature, playing a pivotal role in producing biologically significant carbocycles and heterocycles. The use of both Pd(0) and Ni(0) catalysts, with or without chiral ligands, has been successful in forming five to nine-member ring heterocycles and carbocycles in a simple, cost-effective manner. This review provides a comprehensive survey of the literature from the past decade on the use of reductive Heck cyclization methodology, including mechanistic details as needed.
{"title":"Recent Advance in the Reductive Heck Cyclization for the Formation of Five to Nine Member Rings","authors":"Santanu Chakravorty","doi":"10.2174/0113852728323915240816093254","DOIUrl":"https://doi.org/10.2174/0113852728323915240816093254","url":null,"abstract":": Palladium-catalyzed reactions are widely used for creating carbon-carbon and carbon-heteroatom bonds, with the Heck reaction being particularly valuable for forming rings of various sizes, including mediumsized rings. Recent reports have shown the synthetic potential of intramolecular Heck reactions for assembling rings of seven or more members. While the regioselectivity of this cyclization is often unpredictable in the absence of directing groups, the reductive Heck cyclization strategy can help minimize this issue. Nickel catalysts are also valuable due to their abundance and environmentally friendly nature, playing a pivotal role in producing biologically significant carbocycles and heterocycles. The use of both Pd(0) and Ni(0) catalysts, with or without chiral ligands, has been successful in forming five to nine-member ring heterocycles and carbocycles in a simple, cost-effective manner. This review provides a comprehensive survey of the literature from the past decade on the use of reductive Heck cyclization methodology, including mechanistic details as needed.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214513","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-10DOI: 10.2174/0113852728322422240816060345
Ravi Varala, Murali Mohan Achari Kamsali, Ramanaiah S, Mohammed Mujahid Alam
: Di-tert-butyl peroxide (DTBP) is one of the most widely used organic peroxides in a variety of oxidative transformations. The main factors contributing to the increasing use of DTBP are its affordability, minimal environmental impact, great effectiveness, and capacity to substitute scarce or dangerous heavy metal oxidants. We have reviewed critically and succinctly the noteworthy applications of DTBP in heterocyclic ring constructions from 2014 onwards in this decennial update. The main components of this evaluation are the pros and cons of its use, the scope of a synthetic organic transformation, and mechanistic logistics.
{"title":"Di-tert-butyl Peroxide (DTBP)-Promoted Heterocyclic Ring Construction","authors":"Ravi Varala, Murali Mohan Achari Kamsali, Ramanaiah S, Mohammed Mujahid Alam","doi":"10.2174/0113852728322422240816060345","DOIUrl":"https://doi.org/10.2174/0113852728322422240816060345","url":null,"abstract":": Di-tert-butyl peroxide (DTBP) is one of the most widely used organic peroxides in a variety of oxidative transformations. The main factors contributing to the increasing use of DTBP are its affordability, minimal environmental impact, great effectiveness, and capacity to substitute scarce or dangerous heavy metal oxidants. We have reviewed critically and succinctly the noteworthy applications of DTBP in heterocyclic ring constructions from 2014 onwards in this decennial update. The main components of this evaluation are the pros and cons of its use, the scope of a synthetic organic transformation, and mechanistic logistics.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214508","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-06DOI: 10.2174/0113852728331472240826071320
Ashraf A. Aly, Hisham A. Abd El-Naby, Essam Kh. Ahmed, Sageda A. Gedamy, Mohammed B. Alshammari, Akil Ahmed, Stefan Braese
: Pyrano[3,2-c]quinolone and pyrano[2,3-c]quinoline, as promising molecules, have garnered more attention due to their interesting biological properties. This review dealt with the catalytic synthesis of the former candidates in the last 20 years. Multi-component reactions (MCRs) are synthetic routes that produce a single product from three or more reactants in a one-pot step procedure. We herein reported on the advantages of catalysis in synthesizing the target compounds using the MCR sequence. We also discussed the mechanism and explained the chosen catalyst's utility in the target molecules' selectivity. Finally, this recent review focuses on the biological applications of these molecules as anticancer, antimicrobial activities, anti-diabetic, antiinflammatory, anti-Alzheimer, and antitubercular agents.
{"title":"Catalytic Syntheses of Pyrano[3,2-C]Quinolone and -Quinoline Derivatives and their Potential Therapeutic Agents","authors":"Ashraf A. Aly, Hisham A. Abd El-Naby, Essam Kh. Ahmed, Sageda A. Gedamy, Mohammed B. Alshammari, Akil Ahmed, Stefan Braese","doi":"10.2174/0113852728331472240826071320","DOIUrl":"https://doi.org/10.2174/0113852728331472240826071320","url":null,"abstract":": Pyrano[3,2-c]quinolone and pyrano[2,3-c]quinoline, as promising molecules, have garnered more attention due to their interesting biological properties. This review dealt with the catalytic synthesis of the former candidates in the last 20 years. Multi-component reactions (MCRs) are synthetic routes that produce a single product from three or more reactants in a one-pot step procedure. We herein reported on the advantages of catalysis in synthesizing the target compounds using the MCR sequence. We also discussed the mechanism and explained the chosen catalyst's utility in the target molecules' selectivity. Finally, this recent review focuses on the biological applications of these molecules as anticancer, antimicrobial activities, anti-diabetic, antiinflammatory, anti-Alzheimer, and antitubercular agents.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214512","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-04DOI: 10.2174/0113852728316820240815164622
Sheersha Pradhan, Banoth Janhavi, Thangamuthu Mohan Das
Due to the compatibility of binding and undergoing chemical modification of sugar derivatives with a variety of scaffolds, the design of innovative tools for bio-sensing and bio-marking, energy harvesting, drug design, and delivery is growing steadily. Furthermore, the chemistry of partially protected sugars has not been explored well in terms of its applications in smart materials. However, these sugar derivatives possess a unique characteristic balance between hydrophilic and hydrophobic nature, which makes them act as gelator molecules. Several synthetic strategies pertaining to synthesis and applications are known in the literature. The present review mainly focuses on the partially protected monosaccharide-based N-glycosylamines and their applications, with few examples from O- and C-glycosides.
{"title":"Recent Advances in the Synthesis and Applications of Partially Protected N-Glycosylamines","authors":"Sheersha Pradhan, Banoth Janhavi, Thangamuthu Mohan Das","doi":"10.2174/0113852728316820240815164622","DOIUrl":"https://doi.org/10.2174/0113852728316820240815164622","url":null,"abstract":"Due to the compatibility of binding and undergoing chemical modification of sugar derivatives with a variety of scaffolds, the design of innovative tools for bio-sensing and bio-marking, energy harvesting, drug design, and delivery is growing steadily. Furthermore, the chemistry of partially protected sugars has not been explored well in terms of its applications in smart materials. However, these sugar derivatives possess a unique characteristic balance between hydrophilic and hydrophobic nature, which makes them act as gelator molecules. Several synthetic strategies pertaining to synthesis and applications are known in the literature. The present review mainly focuses on the partially protected monosaccharide-based N-glycosylamines and their applications, with few examples from O- and C-glycosides.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214510","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: This review summarizes the recent trends in the transition-metal-catalyzed C-H bond functionalization approach to access C-branched (hetero)aryl/alkenyl/alkyl glycosides with reaction characteristics and proposed mechanisms. Recently, the Transition-metal-catalyzed C-H functionalization has arisen as a groundbreaking and versatile method for producing potent C-branched glycosides feasibly and efficiently. Nowadays, site-selective functionalization of C-H bonds in carbohydrate chemistry is highly demanded, owing to the intricate and highly stable nature of C-H bonds. In this context, we systematically summarize the C-H glycosylation of arenes, C-H arylation of glycoside, and Cattelani-strategy with mechanistic investigation. Also, the applications of transition-metal-catalyzed C-glycosylation for the formation of biologically active molecules are discussed.
{"title":"Emerging Advances in Transition Metal-Catalyzed C-H Bond Functionalizations Towards C-Glycosides","authors":"Zanjila Azeem, Sunny Maurya, Mohammad Ovais, Rekha Sagwan, Atul Dubey, Pintu Kumar Mandal","doi":"10.2174/0113852728326485240815110646","DOIUrl":"https://doi.org/10.2174/0113852728326485240815110646","url":null,"abstract":": This review summarizes the recent trends in the transition-metal-catalyzed C-H bond functionalization approach to access C-branched (hetero)aryl/alkenyl/alkyl glycosides with reaction characteristics and proposed mechanisms. Recently, the Transition-metal-catalyzed C-H functionalization has arisen as a groundbreaking and versatile method for producing potent C-branched glycosides feasibly and efficiently. Nowadays, site-selective functionalization of C-H bonds in carbohydrate chemistry is highly demanded, owing to the intricate and highly stable nature of C-H bonds. In this context, we systematically summarize the C-H glycosylation of arenes, C-H arylation of glycoside, and Cattelani-strategy with mechanistic investigation. Also, the applications of transition-metal-catalyzed C-glycosylation for the formation of biologically active molecules are discussed.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214519","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-29DOI: 10.2174/0113852728315680240815095102
Dnyaneshwar D. Subhedar, Mubarak H. Shaikh, Amol A. Nagargoje, Dhiman Sarkar, Vijay M. Khedkar, Bapurao B. Shingate
Here, we report the solvent-free one-pot multicomponent synthesis of 4-substituted-1,5- benzodiazepine derivatives from O-phenylenediamine, aromatic aldehydes, and dimedone using [DBUH][HSO4] as a catalyst in excellent yields. This process was carried out in search of a reusable, easily accessible, affordable, and efficient catalyst. 1,5-Benzodiazepines demonstrate a new family of good inhibitors with potent anti-mycobacterial properties. The most promising compounds in the present series are 4c, 4i, and 4l which showed excellent activity and inhibited the growth of both MTB H37Ra and M. bovis BCG strains with lower MICs. The most active compounds were further studied for their cytotoxicity against cell lines MCF-7, A549, HCT116, and THP-1 by MTT assays and the compounds were found to be non-toxic. The fact that none of these compounds work against either Gram-positive or Gram-negative bacteria suggests that they are only effective against MTB. The in silico docking of the molecules against mycobacterial enoyl reductase, InhA enzyme could provide well-clustered solutions and have given valuable insights into the thermodynamic elements governing the binding affinities. The findings of this investigation unmistakably point to the discovery of extremely specific and selective MTB inhibitors, which can now be investigated further in search of possible anti-tubercular drugs.
{"title":"[DBUH][HSO4]-Catalyzed Solvent-Free Synthesis of 1,5-Benzodiazepine Derivatives: Bioevaluation and In Silico Molecular Docking Study","authors":"Dnyaneshwar D. Subhedar, Mubarak H. Shaikh, Amol A. Nagargoje, Dhiman Sarkar, Vijay M. Khedkar, Bapurao B. Shingate","doi":"10.2174/0113852728315680240815095102","DOIUrl":"https://doi.org/10.2174/0113852728315680240815095102","url":null,"abstract":"Here, we report the solvent-free one-pot multicomponent synthesis of 4-substituted-1,5- benzodiazepine derivatives from O-phenylenediamine, aromatic aldehydes, and dimedone using [DBUH][HSO4] as a catalyst in excellent yields. This process was carried out in search of a reusable, easily accessible, affordable, and efficient catalyst. 1,5-Benzodiazepines demonstrate a new family of good inhibitors with potent anti-mycobacterial properties. The most promising compounds in the present series are 4c, 4i, and 4l which showed excellent activity and inhibited the growth of both MTB H37Ra and M. bovis BCG strains with lower MICs. The most active compounds were further studied for their cytotoxicity against cell lines MCF-7, A549, HCT116, and THP-1 by MTT assays and the compounds were found to be non-toxic. The fact that none of these compounds work against either Gram-positive or Gram-negative bacteria suggests that they are only effective against MTB. The in silico docking of the molecules against mycobacterial enoyl reductase, InhA enzyme could provide well-clustered solutions and have given valuable insights into the thermodynamic elements governing the binding affinities. The findings of this investigation unmistakably point to the discovery of extremely specific and selective MTB inhibitors, which can now be investigated further in search of possible anti-tubercular drugs.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214514","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-28DOI: 10.2174/0113852728321140240811170956
Fayez Althobaiti
A series of N-(substituted)-4-methyl aniline derivatives (4a,b, 5a,b, 6, 7, 8, and 9) has been designed and synthesized, and their biological activities were also evaluated as potential anti-tumor and tubulin enzyme inhibitors. Among all compounds, compound (8) showed the most potent tubulin aromatase enzyme inhibitory activity in vitro with an IC50 of 157.3 pg/mL compared to the reference inhibitor Dox (IC50 = 227.4 pg/mL). A docking simulation was performed to insert compound (8) into the crystal structure of human aromatase at the active site to determine the probable binding model. Based on the previous results, compound (8) with potent inhibitory activity on tumor growth could be employed as a potential anticancer agent.
{"title":"Synthesis of N-[trisubstitutedphenyl]-4-methyl Aniline Derivatives as Novel Anti-Breast Cancer Agents","authors":"Fayez Althobaiti","doi":"10.2174/0113852728321140240811170956","DOIUrl":"https://doi.org/10.2174/0113852728321140240811170956","url":null,"abstract":"A series of N-(substituted)-4-methyl aniline derivatives (4a,b, 5a,b, 6, 7, 8, and 9) has been designed and synthesized, and their biological activities were also evaluated as potential anti-tumor and tubulin enzyme inhibitors. Among all compounds, compound (8) showed the most potent tubulin aromatase enzyme inhibitory activity in vitro with an IC50 of 157.3 pg/mL compared to the reference inhibitor Dox (IC50 = 227.4 pg/mL). A docking simulation was performed to insert compound (8) into the crystal structure of human aromatase at the active site to determine the probable binding model. Based on the previous results, compound (8) with potent inhibitory activity on tumor growth could be employed as a potential anticancer agent.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214515","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-28DOI: 10.2174/0113852728317835240812102433
Luu D. Huy, Tatiana S. Savinova, Alexey V. Kazantsev, Victoria V. Fokina, Marina V. Donova
: In this paper, we present an efficient procedure for the transformation of a soybean phytosterol mixture into pregna-1,4,16-triene-3,20-dione, which is a key intermediate for the synthesis of valuable corticoids. The possibility of using two alternative methods for 1(2)-dehydrogenation of pregna-4,16-diene-3,20-dione - chemical and microbiological - was shown. Microbiological 3-keto-4-ene steroid 1(2)-dehydrogenation was carried out using actinobacterial cells of Nocardioides simplex VKM Ac-2033D. The structures of the synthesized compounds were confirmed by the IR, MS, and 1H-NMR methods.
{"title":"Synthesis of Pregna-1,4,16-triene-3,20-dione from a Mixture of Soybean Phytosterols using a Combination of Chemical and Microbiological Methods","authors":"Luu D. Huy, Tatiana S. Savinova, Alexey V. Kazantsev, Victoria V. Fokina, Marina V. Donova","doi":"10.2174/0113852728317835240812102433","DOIUrl":"https://doi.org/10.2174/0113852728317835240812102433","url":null,"abstract":": In this paper, we present an efficient procedure for the transformation of a soybean phytosterol mixture into pregna-1,4,16-triene-3,20-dione, which is a key intermediate for the synthesis of valuable corticoids. The possibility of using two alternative methods for 1(2)-dehydrogenation of pregna-4,16-diene-3,20-dione - chemical and microbiological - was shown. Microbiological 3-keto-4-ene steroid 1(2)-dehydrogenation was carried out using actinobacterial cells of Nocardioides simplex VKM Ac-2033D. The structures of the synthesized compounds were confirmed by the IR, MS, and 1H-NMR methods.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214516","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-26DOI: 10.2174/0113852728316945240807114705
Azhaar T. Alsaggaf, Mostafa Sayed, Ahmed I.A. Soliman, Mostafa Ahmed
Organocatalysis has been recognized as a part of chemical research for a long time, and it gained significant attention in catalysis in recent decades. Amine catalyst is a substantial type of organocatalysis, and it is successively employed for the activation of carbonyl compounds. This manuscript delves into the exploration of a proline-based organocatalyst for the synthesis of arylidene benzofuranone intermediates, a critical step that facilitates the subsequent construction of aurone-derived azadienes. In this work, we successfully reported the synthesis of arylidene benzofuranone intermediates through Aldol condensation of benzofuranone with different aldehydes enabled by proline-derived organic catalysts. To achieve this strategy, six examples of amine organocatalysts (A1-A6) were evaluated to showcase the optimal catalyst for this transformation. Moreover, the arylidene benzofuranone intermediates were further employed for the synthesis of interesting aurone-derived azadiene substrates through its reaction with TsNH2. Notably, the using of organocatalyst A6 resulted in the delivery of the product with the best yield (94% isolated yield). Under the optimized conditions, different aromatic and heterocyclic containing aldehydes were effectively tolerated to generate the corresponding arylidene benzofuranone intermediates, which further converted to the azadiene products in high to excellent yield. The claimed structures were confirmed by the spectral analysis.
{"title":"Proline-based Organocatalyst for the Synthesis of Arylidene Benzofuranone Intermediates Enabling the Construction of Aurone-derived Azadienes","authors":"Azhaar T. Alsaggaf, Mostafa Sayed, Ahmed I.A. Soliman, Mostafa Ahmed","doi":"10.2174/0113852728316945240807114705","DOIUrl":"https://doi.org/10.2174/0113852728316945240807114705","url":null,"abstract":"Organocatalysis has been recognized as a part of chemical research for a long time, and it gained significant attention in catalysis in recent decades. Amine catalyst is a substantial type of organocatalysis, and it is successively employed for the activation of carbonyl compounds. This manuscript delves into the exploration of a proline-based organocatalyst for the synthesis of arylidene benzofuranone intermediates, a critical step that facilitates the subsequent construction of aurone-derived azadienes. In this work, we successfully reported the synthesis of arylidene benzofuranone intermediates through Aldol condensation of benzofuranone with different aldehydes enabled by proline-derived organic catalysts. To achieve this strategy, six examples of amine organocatalysts (A1-A6) were evaluated to showcase the optimal catalyst for this transformation. Moreover, the arylidene benzofuranone intermediates were further employed for the synthesis of interesting aurone-derived azadiene substrates through its reaction with TsNH2. Notably, the using of organocatalyst A6 resulted in the delivery of the product with the best yield (94% isolated yield). Under the optimized conditions, different aromatic and heterocyclic containing aldehydes were effectively tolerated to generate the corresponding arylidene benzofuranone intermediates, which further converted to the azadiene products in high to excellent yield. The claimed structures were confirmed by the spectral analysis.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142214518","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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