Pub Date : 2025-09-17DOI: 10.1080/00397911.2025.2558714
Tarik E. Ali (Conceptualization Funding acquisition Investigation Writing – original draft Writing – review & editing) , Mohammed A. Assiri (Formal analysis Resources Software) , Ali A. Shati (Formal analysis Software Visualization) , Mohammad Y. Alfaifi (Formal analysis Software Visualization) , Serag E. I. Elbehairi (Formal analysis Investigation Methodology Software Validation)
One-pot synthetic strategy was designed for the synthesis of novel diethyl (pyrazolo- [4,3-c]quinolin-3-yl)phosphonates and diethyl (isoxazolo[4,5-c]quinolin-3-yl)phosphonate. The novel phosphorus heterocycles of types 1,4,2-diazaphospholes, 1,4,2-oxazaphosphinines and 1,4,2-diazaphosphinines containing 4-quinolinone ring were also achieved. The designed strategies depended on a three component reaction of 4-oxo-1,4-dihydroquinoline-3-carboxaldehyde (1) with a series of bi-nucleophilic nitrogen reagents in the presence of diethyl phosphite under solvent-free and catalyst-free conditions. This newly developed approach helped to synthesize new ten organophosphorus compounds with good yields. The IR, MS and NMR spectroscopic tools were used to characterize the isolated compounds, and their formation mechanisms were discussed. All synthesized compounds were evaluated for their in vitro cytotoxicity against A549, MDA-MB-231 and HeLa cell lines. Compounds 10 and 11 exhibited the most potent cytotoxicity, in comparison with doxorubicin. Furthermore, these two compounds significantly induced early apoptosis and reducing cell viability in the studied tumor cells. Additionally, both compounds 10 and 11 demonstrated promising ability to arrest the cell cycle at the S and G2 phases. In silico ADMET predictions indicated that compounds 10 and 11 possess higher predicted human intestinal absorption (∼89.6% vs. 51.85% for doxorubicin), absence of AMES mutagenicity, and lower predicted acute and chronic oral toxicities in rats. Potential hepatotoxicity and CYP enzyme inhibition were also observed. Molecular docking against EGFR-T790M/V948R revealed that both compound 10 and 11 exhibited a binding affinity of −8.4 and 8.9 kcal/mol, respectively. The interactions of both compounds with key amino acid residues (e.g., LEU 718, VAL 726, ALA 743, MET 790, ASP 855) were consistent with their strong in vitro cytotoxic activity against A549 (EGFR-mutated) cells, supporting their potential as EGFR-targeted anticancer agents.
设计了一锅法合成新型（吡唑啉- [4,3-c]喹啉-3-基）膦酸二乙酯和（异恶唑啉[4,5-c]喹啉-3-基）膦酸二乙酯。还获得了1,4,2-二氮磷孔型、1,4,2-恶氮磷和含4-喹啉酮环的1,4,2-二氮磷的新型磷杂环。设计的策略依赖于在无溶剂和无催化剂的条件下，4-氧-1,4-二氢喹啉-3-甲醛(1)与一系列双亲核氮试剂在亚磷酸二乙酯存在下的三组分反应。这种新方法有助于合成新的十种有机磷化合物，收率高。利用红外光谱、质谱和核磁共振光谱对分离得到的化合物进行了表征，并对其形成机理进行了探讨。所有合成的化合物对A549、MDA-MB-231和HeLa细胞株的体外细胞毒性进行了评价。与阿霉素相比，化合物10和11表现出最强的细胞毒性。此外，这两种化合物显著诱导肿瘤细胞早期凋亡和降低细胞活力。此外，化合物10和11都显示出在S期和G2期阻止细胞周期的能力。ADMET预测表明，化合物10和11具有较高的预测人体肠道吸收（~ 89.6%，而阿霉素为51.85%），没有AMES诱变性，并且在大鼠中具有较低的预测急性和慢性口服毒性。潜在的肝毒性和CYP酶抑制也被观察到。与EGFR-T790M/V948R的分子对接表明，化合物10和11的结合亲和力分别为−8.4和8.9 kcal/mol。这两种化合物与关键氨基酸残基（如LEU 718， VAL 726, ALA 743, MET 790, ASP 855）的相互作用与它们对A549 （egfr突变）细胞的强体外细胞毒活性一致，支持它们作为egfr靶向抗癌药物的潜力。
{"title":"Synthesis and anticancer evaluation of novel azoloquinolinyl phosphonates, 1,4,2-Diazaphospholes, 1,4,2-Oxazaphosphinines, and 1,4,2-Diazaphosphinines containing a 4-quinolinone ring: Cytotoxicity, apoptosis, cell cycle analysis, In silico ADMET, and molecular docking studies","authors":"Tarik E. Ali (Conceptualization Funding acquisition Investigation Writing – original draft Writing – review & editing) , Mohammed A. Assiri (Formal analysis Resources Software) , Ali A. Shati (Formal analysis Software Visualization) , Mohammad Y. Alfaifi (Formal analysis Software Visualization) , Serag E. I. Elbehairi (Formal analysis Investigation Methodology Software Validation)","doi":"10.1080/00397911.2025.2558714","DOIUrl":"10.1080/00397911.2025.2558714","url":null,"abstract":"<div><div>One-pot synthetic strategy was designed for the synthesis of novel diethyl (pyrazolo- [4,3-c]quinolin-3-yl)phosphonates and diethyl (isoxazolo[4,5-c]quinolin-3-yl)phosphonate. The novel phosphorus heterocycles of types 1,4,2-diazaphospholes, 1,4,2-oxazaphosphinines and 1,4,2-diazaphosphinines containing 4-quinolinone ring were also achieved. The designed strategies depended on a three component reaction of 4-oxo-1,4-dihydroquinoline-3-carboxaldehyde (<strong>1</strong>) with a series of <em>bi</em>-nucleophilic nitrogen reagents in the presence of diethyl phosphite under solvent-free and catalyst-free conditions. This newly developed approach helped to synthesize new ten organophosphorus compounds with good yields. The IR, MS and NMR spectroscopic tools were used to characterize the isolated compounds, and their formation mechanisms were discussed. All synthesized compounds were evaluated for their in <em>vitro</em> cytotoxicity against A549, MDA-MB-231 and HeLa cell lines. Compounds <strong>10</strong> and <strong>11</strong> exhibited the most potent cytotoxicity, in comparison with doxorubicin. Furthermore, these two compounds significantly induced early apoptosis and reducing cell viability in the studied tumor cells. Additionally, both compounds <strong>10</strong> and <strong>11</strong> demonstrated promising ability to arrest the cell cycle at the S and G2 phases. In <em>silico</em> ADMET predictions indicated that compounds <strong>10</strong> and <strong>11</strong> possess higher predicted human intestinal absorption (∼89.6% vs. 51.85% for doxorubicin), absence of AMES mutagenicity, and lower predicted acute and chronic oral toxicities in rats. Potential hepatotoxicity and CYP enzyme inhibition were also observed. Molecular docking against EGFR-T790M/V948R revealed that both compound <strong>10</strong> and <strong>11</strong> exhibited a binding affinity of −8.4 and 8.9 kcal/mol, respectively. The interactions of both compounds with key amino acid residues (e.g., LEU 718, VAL 726, ALA 743, MET 790, ASP 855) were consistent with their strong in <em>vitro</em> cytotoxic activity against A549 (EGFR-mutated) cells, supporting their potential as EGFR-targeted anticancer agents.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 18","pages":"Pages 1413-1435"},"PeriodicalIF":1.8,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145108292","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}
In the current scenario, the use of nature-friendly methods in organic synthesis is regarded as invaluable and irreplaceable. Significant progress has been made in developing more sustainable and eco-friendly approaches for various organic syntheses and transformations. Within the scope of green synthesis, ILs have attracted a lot of interest since their special features fit for sustainable chemistry. Organic synthesis has increasingly utilized ILs as green catalysts and solvents for the development of countless heterocycles. Among these, imidazole is recognized as a highly valuable and preferred heterocyclic motif. It presents interesting chances for finding ideal structures in the synthesis of synthetic compounds with possible therapeutic uses and other major prospects. A diverse array of ILs has been successfully exploited toward the development of imidazoles. Therefore, this review article offers a thorough review of current studies on the function of ecologically safe ILs in producing a wide range of valuable imidazoles.
{"title":"IL-assisted strategy for imidazole: A green recipe","authors":"Vaishali (Writing – original draft) , Shubham Sharma (Supervision Writing – review & editing) , Vinod (Conceptualization Investigation Methodology) , Swati Rani (Software Validation Visualization) , Man Vir Singh (Investigation Validation) , Sodeeq Aderotimi Salami (Validation Visualization) , Sobhi M. Gomha (Project administration Supervision)","doi":"10.1080/00397911.2025.2521832","DOIUrl":"10.1080/00397911.2025.2521832","url":null,"abstract":"<div><div>In the current scenario, the use of nature-friendly methods in organic synthesis is regarded as invaluable and irreplaceable. Significant progress has been made in developing more sustainable and eco-friendly approaches for various organic syntheses and transformations. Within the scope of green synthesis, ILs have attracted a lot of interest since their special features fit for sustainable chemistry. Organic synthesis has increasingly utilized ILs as green catalysts and solvents for the development of countless heterocycles. Among these, imidazole is recognized as a highly valuable and preferred heterocyclic motif. It presents interesting chances for finding ideal structures in the synthesis of synthetic compounds with possible therapeutic uses and other major prospects. A diverse array of ILs has been successfully exploited toward the development of imidazoles. Therefore, this review article offers a thorough review of current studies on the function of ecologically safe ILs in producing a wide range of valuable imidazoles.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 18","pages":"Pages 1351-1389"},"PeriodicalIF":1.8,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145108728","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 : 2025-09-17DOI: 10.1080/00397911.2025.2550435
Chuang Liu (Writing – original draft Writing – review & editing) , Yang Zhou (Formal analysis Supervision) , Wenqiang Pei (Data curation Investigation) , Jinjun Hou (Formal analysis Supervision Validation) , Huali Long (Data curation Supervision) , Zijia Zhang (Conceptualization Supervision Validation) , Qinhua Chen (Funding acquisition Resources) , Yang Yang (Funding acquisition Investigation Resources) , Min Lei (Conceptualization Methodology Supervision Writing – original draft) , Wanying Wu (Funding acquisition Project administration Resources Supervision)
A green and efficient method for synthesizing imidazolidin-4-one derivatives catalyzed by thiamin hydrochloride (VB1) has been developed. This protocol involves the reaction of α-amino amides with carbonyl compounds (aldehydes or ketones) in the presence of VB1 (5 mol%) in EtOH, affording the target products in 50–85% yields. The reaction demonstrates broad substrate compatibility, accommodating aromatic aldehydes, heteroaromatic aldehydes, alkyl aldehydes, and alkyl ketones. Notably, estrone as a ketone substrate successfully undergoes condensation, yielding the corresponding product in 72% yield. The VB1 catalyst offers advantages such as short reaction times, high efficiency, excellent environmental friendliness, and recyclability, maintaining performance over at least three cycles.
{"title":"Thiamin hydrochloride (VB1): A green and efficient catalyst for the synthesis of imidazolidin-4-ones","authors":"Chuang Liu (Writing – original draft Writing – review & editing) , Yang Zhou (Formal analysis Supervision) , Wenqiang Pei (Data curation Investigation) , Jinjun Hou (Formal analysis Supervision Validation) , Huali Long (Data curation Supervision) , Zijia Zhang (Conceptualization Supervision Validation) , Qinhua Chen (Funding acquisition Resources) , Yang Yang (Funding acquisition Investigation Resources) , Min Lei (Conceptualization Methodology Supervision Writing – original draft) , Wanying Wu (Funding acquisition Project administration Resources Supervision)","doi":"10.1080/00397911.2025.2550435","DOIUrl":"10.1080/00397911.2025.2550435","url":null,"abstract":"<div><div>A green and efficient method for synthesizing imidazolidin-4-one derivatives catalyzed by thiamin hydrochloride (VB<sub>1</sub>) has been developed. This protocol involves the reaction of α-amino amides with carbonyl compounds (aldehydes or ketones) in the presence of VB<sub>1</sub> (5 mol%) in EtOH, affording the target products in 50–85% yields. The reaction demonstrates broad substrate compatibility, accommodating aromatic aldehydes, heteroaromatic aldehydes, alkyl aldehydes, and alkyl ketones. Notably, estrone as a ketone substrate successfully undergoes condensation, yielding the corresponding product in 72% yield. The VB<sub>1</sub> catalyst offers advantages such as short reaction times, high efficiency, excellent environmental friendliness, and recyclability, maintaining performance over at least three cycles.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 18","pages":"Pages 1390-1401"},"PeriodicalIF":1.8,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145108729","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}
A new method for the synthesis of various pyrrole-3-carboximidamide (imidate) derivatives from the multicomponent reaction of alkynes, trichloroacetamide (imidate), and nitro compounds-trichloroacetonitrile adducts under ultrasound (US) irradiation has been reported. The reaction of nitromethane (or ethane) with trichloroacetonitrile in the presence of sodium hydride as a base led to the formation of nitro compounds-trichloroacetonitrile adducts, which subsequently led to the synthesis of new pyrrole-3-carboxyimidamide (imidate) derivatives in good yields by the addition of alkynes and trichloroacetamide (imidate). The use of an inexpensive copper (I) catalyst, under ultrasonic conditions as an energy source for 50 min, in the absence of ligands and oxidants, CH2Cl2 solvent, and the synthesis and identification of new compounds are important in this research. The combination of mild reaction conditions, one-pot, five-component, catalytic systems, available starting materials, and ease of purification methods facilitates the synthesis of diverse new substituted pyrroles, including amidine and imidate skeletons.
{"title":"Innovative ultrasound‐assisted synthesis of new highly functionalized pyrroles derivatives from alkynes, trichloroacet-amidine(imidate), and nitro compounds-trichloroacetonitrile adducts","authors":"Manijeh Nematpour (Data curation Formal analysis Supervision Writing – review & editing)","doi":"10.1080/00397911.2025.2558717","DOIUrl":"10.1080/00397911.2025.2558717","url":null,"abstract":"<div><div>A new method for the synthesis of various pyrrole-3-carboximidamide (imidate) derivatives from the multicomponent reaction of alkynes, trichloroacetamide (imidate), and nitro compounds-trichloroacetonitrile adducts under ultrasound (US) irradiation has been reported. The reaction of nitromethane (or ethane) with trichloroacetonitrile in the presence of sodium hydride as a base led to the formation of nitro compounds-trichloroacetonitrile adducts, which subsequently led to the synthesis of new pyrrole-3-carboxyimidamide (imidate) derivatives in good yields by the addition of alkynes and trichloroacetamide (imidate). The use of an inexpensive copper (I) catalyst, under ultrasonic conditions as an energy source for 50 min, in the absence of ligands and oxidants, CH<sub>2</sub>Cl<sub>2</sub> solvent, and the synthesis and identification of new compounds are important in this research. The combination of mild reaction conditions, one-pot, five-component, catalytic systems, available starting materials, and ease of purification methods facilitates the synthesis of diverse new substituted pyrroles, including amidine and imidate skeletons.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 18","pages":"Pages 1402-1412"},"PeriodicalIF":1.8,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145108724","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 : 2025-09-02DOI: 10.1080/00397911.2025.2548301
Yawen Hu (Conceptualization Data curation Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) , Li Xu (Data curation Formal analysis) , Xue Jiang (Data curation Supervision) , Haiyang Guo (Formal analysis Investigation) , Di Wu (Conceptualization Data curation Methodology Writing – review & editing)
A recyclable ligand chitosan was developed for the copper-catalyzed Ullmann-type cross-coupling reaction of aryl halides with amines. A variety of functionalized (hetero)aryl halides reacted smoothly with pyrazole, imidazole, aliphatic amines and ammonia to provide a wide range of (hetero)aryl amines in good to excellent yields under the catalyst of Cu2O/chitosan system. This method has the advantages of wide substrate range, high chemoselectivity, and good functional group compatibility. The ligand is easily recycled and no significant decrease in the catalytic potency after being reused 7 times.
{"title":"Recyclable chitosan for copper-catalyzed Ullmann C-N coupling reaction","authors":"Yawen Hu (Conceptualization Data curation Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) , Li Xu (Data curation Formal analysis) , Xue Jiang (Data curation Supervision) , Haiyang Guo (Formal analysis Investigation) , Di Wu (Conceptualization Data curation Methodology Writing – review & editing)","doi":"10.1080/00397911.2025.2548301","DOIUrl":"10.1080/00397911.2025.2548301","url":null,"abstract":"<div><div>A recyclable ligand chitosan was developed for the copper-catalyzed Ullmann-type cross-coupling reaction of aryl halides with amines. A variety of functionalized (hetero)aryl halides reacted smoothly with pyrazole, imidazole, aliphatic amines and ammonia to provide a wide range of (hetero)aryl amines in good to excellent yields under the catalyst of Cu<sub>2</sub>O/chitosan system. This method has the advantages of wide substrate range, high chemoselectivity, and good functional group compatibility. The ligand is easily recycled and no significant decrease in the catalytic potency after being reused 7 times.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 17","pages":"Pages 1340-1350"},"PeriodicalIF":1.8,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048723","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 : 2025-09-02DOI: 10.1080/00397911.2025.2547391
Zhila Zharf Zaki (Conceptualization Investigation Methodology Writing – original draft) , Abbas Ali Esmaeili (Conceptualization Investigation Project administration Supervision Writing – review & editing)
A novel and efficient one-pot, three-component reaction was developed for the synthesis of 2-phenyl-4-((arylamino)methylene)-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one derivatives. The reaction proceeds via the condensation of 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one, aniline derivatives, and trimethyl orthoformate under solvent-free conditions at 110 °C. This green protocol integrates multiple pharmacophores, offering potential for biological applications. Key advantages include operational simplicity, high yields (80%–92%), and the absence of catalysts and solvents. IR,1H,1³C, 19F NMR, mass spectrometry, and elemental analysis confirmed product structures.
{"title":"Efficient solvent- and catalyst-free one-pot synthesis of novel trifluoromethylated pyrazole derivatives","authors":"Zhila Zharf Zaki (Conceptualization Investigation Methodology Writing – original draft) , Abbas Ali Esmaeili (Conceptualization Investigation Project administration Supervision Writing – review & editing)","doi":"10.1080/00397911.2025.2547391","DOIUrl":"10.1080/00397911.2025.2547391","url":null,"abstract":"<div><div>A novel and efficient one-pot, three-component reaction was developed for the synthesis of 2-phenyl-4-((arylamino)methylene)-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one derivatives. The reaction proceeds via the condensation of 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one, aniline derivatives, and trimethyl orthoformate under solvent-free conditions at 110 °C. This green protocol integrates multiple pharmacophores, offering potential for biological applications. Key advantages include operational simplicity, high yields (80%–92%), and the absence of catalysts and solvents. IR,<sup>1</sup>H,<sup>1</sup>³C, <sup>19</sup>F NMR, mass spectrometry, and elemental analysis confirmed product structures.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 17","pages":"Pages 1306-1314"},"PeriodicalIF":1.8,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048720","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}
A direct α‑iodination of α,β‑unsaturated aldehydes and ketones carried out without metal bases at room temperature in water, utilizing 1–7 equivalents of pyridine, is reported herein. High yields are obtained in the iodination of enals. Liquid and solid enones give good to moderate yields of the iodo products. Pyridine was the most effective catalyst among the secondary and tertiary amines studied. An absence of water reduces yields, while yields of (Z)-α-iodo-α,β-unsaturated aldehydes and ketones improved significantly with water as the solvent. The reactivities of the enals and, to a certain extent, enones such as (E)-4-phenylbut-3-en-2-one and mesityl oxide could be accounted for by the Mayr electrophilicity parameter (E). However, the lower reactivities of (E)-hex-4-en-3-one and chalcone were the outliers of their E parameter values prediction.
{"title":"The impact of water and pyridine on the α-iodination of α,β-unsaturated aldehydes and ketones","authors":"Phutawan Kittithanaluk (Investigation Methodology Visualization) , Pakorn Bovonsombat (Conceptualization Formal analysis Investigation Methodology Project administration Supervision Writing – original draft Writing – review & editing) , Eaint Thu Thu Mon (Investigation) , Fahsai Ploymanee (Investigation) , Nattawadee Srikamhom (Investigation) , Jing Ting We (Investigation) , Sirirat Choosakoonkriang (Investigation Resources) , Amber Hocks (Investigation)","doi":"10.1080/00397911.2025.2548310","DOIUrl":"10.1080/00397911.2025.2548310","url":null,"abstract":"<div><div>A direct α‑iodination of α,β‑unsaturated aldehydes and ketones carried out without metal bases at room temperature in water, utilizing 1–7 equivalents of pyridine, is reported herein. High yields are obtained in the iodination of enals. Liquid and solid enones give good to moderate yields of the iodo products. Pyridine was the most effective catalyst among the secondary and tertiary amines studied. An absence of water reduces yields, while yields of (<em>Z</em>)-α-iodo-α,β-unsaturated aldehydes and ketones improved significantly with water as the solvent. The reactivities of the enals and, to a certain extent, enones such as (<em>E</em>)-4-phenylbut-3-en-2-one and mesityl oxide could be accounted for by the Mayr electrophilicity parameter (<em>E</em>). However, the lower reactivities of (<em>E</em>)-hex-4-en-3-one and chalcone were the outliers of their <em>E</em> parameter values prediction.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 17","pages":"Pages 1315-1327"},"PeriodicalIF":1.8,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048722","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}
The catalyst plays an important role while the organic transformations are taking place. They enhance the reaction process by reducing the reaction time and provide highly efficient yields. Imidazole is one of the most common heterocyclic rings with several pharmaceutical and other significances. Trisubstituted imidazoles have various scientific and biological applications among the different types of imidazole rings. This review compiles the list of catalysts used in the synthesis of trisubstituted imidazoles using benzil, aldehydes and ammonium sources like ammonium acetate or urea. Hence, the study evaluates the efficiency of different catalytic systems in promoting the above-mentioned multicomponent reaction, leading to enhanced yields and reduced reaction times.
{"title":"Significant advances in catalytic strategies for the synthesis of trisubstituted imidazoles: a review","authors":"Saloni Mangal (Writing – original draft) , Salahuddin (Methodology Writing – review & editing) , Avijit Mazumder (Supervision) , Rajnish Kumar (Validation Visualization) , Sapna Rani (Data curation) , Mohamed Jawed Ahsan (Investigation) , Mohammad Shahar Yar (Conceptualization Formal analysis)","doi":"10.1080/00397911.2025.2505901","DOIUrl":"10.1080/00397911.2025.2505901","url":null,"abstract":"<div><div>The catalyst plays an important role while the organic transformations are taking place. They enhance the reaction process by reducing the reaction time and provide highly efficient yields. Imidazole is one of the most common heterocyclic rings with several pharmaceutical and other significances. Trisubstituted imidazoles have various scientific and biological applications among the different types of imidazole rings. This review compiles the list of catalysts used in the synthesis of trisubstituted imidazoles using benzil, aldehydes and ammonium sources like ammonium acetate or urea. Hence, the study evaluates the efficiency of different catalytic systems in promoting the above-mentioned multicomponent reaction, leading to enhanced yields and reduced reaction times.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 17","pages":"Pages 1281-1305"},"PeriodicalIF":1.8,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048719","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 : 2025-09-02DOI: 10.1080/00397911.2025.2548309
Austin Carter (Data curation Methodology Writing – review & editing) , Daniel Wright (Data curation Methodology) , Giavanna Alongi (Data curation) , Christopher G. Hamaker (Data curation) , Shawn R. Hitchcock (Conceptualization Funding acquisition Methodology Project administration Supervision Writing – original draft) , Desmond H. Murray (Conceptualization Data curation Methodology Writing – review & editing)
The drug ataluren has been prepared using a one-pot synthesis of 1,2,4-oxadiazoles from amidoximes. This one-pot approach involves the in situ formation of O-acylamidoximes via the DMAP catalyzed O-acylation of amidoximes followed by cyclization in the presence of potassium hydroxide in DMSO. Using this methodology, a series of 17 examples of 1,2,4-oxadiazoles were formed in isolated yields up to 94% and the synthesis of ataluren was completed.
{"title":"Synthetic preparation of Ataluren via a one-pot synthesis of 1,2,4-oxadiazoles employing a DMAP catalyzed amidoxime O-acylation/cyclization pathway","authors":"Austin Carter (Data curation Methodology Writing – review & editing) , Daniel Wright (Data curation Methodology) , Giavanna Alongi (Data curation) , Christopher G. Hamaker (Data curation) , Shawn R. Hitchcock (Conceptualization Funding acquisition Methodology Project administration Supervision Writing – original draft) , Desmond H. Murray (Conceptualization Data curation Methodology Writing – review & editing)","doi":"10.1080/00397911.2025.2548309","DOIUrl":"10.1080/00397911.2025.2548309","url":null,"abstract":"<div><div>The drug ataluren has been prepared using a one-pot synthesis of 1,2,4-oxadiazoles from amidoximes. This one-pot approach involves the <em>in situ</em> formation of <em>O</em>-acylamidoximes via the DMAP catalyzed <em>O</em>-acylation of amidoximes followed by cyclization in the presence of potassium hydroxide in DMSO. Using this methodology, a series of 17 examples of 1,2,4-oxadiazoles were formed in isolated yields up to 94% and the synthesis of ataluren was completed.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 17","pages":"Pages 1328-1339"},"PeriodicalIF":1.8,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048721","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 : 2025-08-18DOI: 10.1080/00397911.2025.2535655
Ajay J. Jani (Conceptualization Data curation Formal analysis Investigation Methodology Software Visualization Writing – original draft Writing – review & editing) , Jignesh H. Kamdar (Methodology Software Validation Visualization Writing – original draft) , Satishkumar D. Tala (Conceptualization Investigation Methodology Project administration Resources Supervision Writing – original draft Writing – review & editing)
A series of benzoxazole-piperazine hybrids (9a–n) has been synthesized via a multistep approach incorporating the Mitsunobu reaction. These compounds were obtained in good yields using cost-effective and readily available starting materials under mild reaction conditions. Structural characterization was performed using 1H NMR,13C NMR, LCMS, elemental analysis, and FTIR spectroscopy. The antimicrobial potential of 9a–n was assessed against bacterial strains Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli and fungal strains Aspergillus niger, and Candida albicans. Notably, compounds 9b, 9c and 9f exhibited potent antibacterial activity, comparable to chloramphenicol and gentamicin, and antifungal activity similar to nystatin. Molecular docking and dynamics simulations suggested that 9f inhibits E. coli DNA gyrase, forming a stable protein-ligand complex with strong binding interactions and low docking scores. Furthermore, in silico ADMET analysis indicated favorable pharmacokinetic properties with no significant toxicity concerns, highlighting their potential as promising antimicrobial agents.
{"title":"Design, synthesis, antimicrobial evaluation, in-silico molecular docking, and ADME-T evaluation of novel benzoxazole-piperazine hybrids with amide linkage","authors":"Ajay J. Jani (Conceptualization Data curation Formal analysis Investigation Methodology Software Visualization Writing – original draft Writing – review & editing) , Jignesh H. Kamdar (Methodology Software Validation Visualization Writing – original draft) , Satishkumar D. Tala (Conceptualization Investigation Methodology Project administration Resources Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2535655","DOIUrl":"10.1080/00397911.2025.2535655","url":null,"abstract":"<div><div>A series of benzoxazole-piperazine hybrids (<strong>9a–n</strong>) has been synthesized via a multistep approach incorporating the Mitsunobu reaction. These compounds were obtained in good yields using cost-effective and readily available starting materials under mild reaction conditions. Structural characterization was performed using <sup>1</sup>H NMR,<sup>13</sup>C NMR, LCMS, elemental analysis, and FTIR spectroscopy. The antimicrobial potential of <strong>9a–n</strong> was assessed against bacterial strains <em>Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa,</em> and <em>Escherichia coli</em> and fungal strains <em>Aspergillus niger,</em> and <em>Candida albicans</em>. Notably, compounds <strong>9b</strong>, <strong>9c</strong> and <strong>9f</strong> exhibited potent antibacterial activity, comparable to chloramphenicol and gentamicin, and antifungal activity similar to nystatin. Molecular docking and dynamics simulations suggested that <strong>9f</strong> inhibits <em>E. coli</em> DNA gyrase, forming a stable protein-ligand complex with strong binding interactions and low docking scores. Furthermore, in silico ADMET analysis indicated favorable pharmacokinetic properties with no significant toxicity concerns, highlighting their potential as promising antimicrobial agents.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 16","pages":"Pages 1228-1246"},"PeriodicalIF":1.8,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144908835","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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