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Organocatalysis in tetrasubstituted imidazole synthesis: A critical review of recent progress 四取代咪唑合成中的有机催化：最新进展综述
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-18 DOI: 10.1080/00397911.2025.2451416
Saptadwipa Bhattacharjee , Puja Basak , Pranab Ghosh
{"title":"Organocatalysis in tetrasubstituted imidazole synthesis: A critical review of recent progress","authors":"Saptadwipa Bhattacharjee ,&nbsp;Puja Basak ,&nbsp;Pranab Ghosh","doi":"10.1080/00397911.2025.2451416","DOIUrl":"10.1080/00397911.2025.2451416","url":null,"abstract":"<div><div>Tetrasubstituted imidazoles are a class of privileged heterocycles with diverse applications in medicinal chemistry, materials science, and catalysis. Organocatalysis has emerged as a powerful tool for the synthesis of these complex molecules. This review provides a critical overview of recent progress in organocatalytic approaches to tetrasubstituted imidazole synthesis, highlighting key advances, challenges, and opportunities in this rapidly evolving field. We discuss the scope of various organocatalytic strategies, and provide insights into the outcomes of these reactions. This review aims to provide a comprehensive and authoritative assessment of the current state of the art in organocatalytic tetrasubstituted imidazole synthesis, and to identify future directions for research in this exciting area.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 7","pages":"Pages 521-535"},"PeriodicalIF":1.8,"publicationDate":"2025-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143609230","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}
引用次数: 0
Recent applications of phenyl hydrazine in photoinduced chemical transformations 苯肼在光致化学转化中的最新应用
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-17 DOI: 10.1080/00397911.2024.2434044
Sangita Yadav , Rohit Kumar , Vishal Srivastava , Praveen P. Singh , Pravin K. Singh
{"title":"Recent applications of phenyl hydrazine in photoinduced chemical transformations","authors":"Sangita Yadav ,&nbsp;Rohit Kumar ,&nbsp;Vishal Srivastava ,&nbsp;Praveen P. Singh ,&nbsp;Pravin K. Singh","doi":"10.1080/00397911.2024.2434044","DOIUrl":"10.1080/00397911.2024.2434044","url":null,"abstract":"<div><div>Phenyl hydrazine has attracted attention in photoredox catalytic synthetic strategies for the formation of carbon-carbon (C-C) bond and Carbon-Heteroatom (C-N, C = N, C-P, C-S, S-N) bonds, because of low cost and ease of availability make it a promising alternative method for typical transition metal complex-based photocatalyzed synthesis. In this review, we have focused on the recent radical coupling ­reactions of phenyl hydrazine <em>via</em> photochemical strategies to form carbon–carbon and carbon–heteroatom (N, P, S) bonds along with mechanism involved in their reaction.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 2","pages":"Pages 93-115"},"PeriodicalIF":1.8,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129700","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}
引用次数: 0
The reactivity of indole-[3,4-b]-azepin-1,5-dione for halogenations and synthesis of alkylamine substituted indole-[3,4-b]-azepine derivatives 吲哚-[3,4-b]-氮平-1,5-二酮在卤化和烷基胺取代吲哚-[3,4-b]-氮平衍生物合成中的反应性
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-17 DOI: 10.1080/00397911.2024.2438716
Aakansha Negi , Anup A. Gupta , Chichanbemo E. Kikon , Swathilakshmi S. , Santosh Kumar Guru , Venkata Rao Kaki
{"title":"The reactivity of indole-[3,4-b]-azepin-1,5-dione for halogenations and synthesis of alkylamine substituted indole-[3,4-b]-azepine derivatives","authors":"Aakansha Negi ,&nbsp;Anup A. Gupta ,&nbsp;Chichanbemo E. Kikon ,&nbsp;Swathilakshmi S. ,&nbsp;Santosh Kumar Guru ,&nbsp;Venkata Rao Kaki","doi":"10.1080/00397911.2024.2438716","DOIUrl":"10.1080/00397911.2024.2438716","url":null,"abstract":"<div><div>A novel method is developed for the synthesis of amine-substituted indole [3,4-<em>b</em>] azepine derivatives. <em>In-situ</em> chlorination, followed by nucleophilic substitution of 1,5-dichloro azepino[3,4-<em>b</em>] indole with respective amines yields the desired compounds. The reactivity of the azepinone ring toward chlorination reactions is intriguing and gives either rearranged or hydrolyzed products under aqueous work up conditions. In brominated azepinones, elimination is favored over nucleophilic substitution reaction. The synthesized compounds displayed <em>in vitro</em> cytotoxicity against human cancer cell lines.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 2","pages":"Pages 166-174"},"PeriodicalIF":1.8,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129706","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}
引用次数: 0
Synthesis and biological evaluation of aryl derivatives of indole-1,3,4-thiadiazole as anticancer agents 吲哚-1,3,4-噻二唑抗癌芳基衍生物的合成及生物学评价
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-17 DOI: 10.1080/00397911.2024.2431034
Sudhakar Kalagara , Sudhakar Reddy Baddam , Srinivas Ganta , Balaraju Vudari , Sreenivas Enaganti , Anil Damarancha , Laxminarayana Eppakayala
{"title":"Synthesis and biological evaluation of aryl derivatives of indole-1,3,4-thiadiazole as anticancer agents","authors":"Sudhakar Kalagara ,&nbsp;Sudhakar Reddy Baddam ,&nbsp;Srinivas Ganta ,&nbsp;Balaraju Vudari ,&nbsp;Sreenivas Enaganti ,&nbsp;Anil Damarancha ,&nbsp;Laxminarayana Eppakayala","doi":"10.1080/00397911.2024.2431034","DOIUrl":"10.1080/00397911.2024.2431034","url":null,"abstract":"<div><div>A library of aryl substituted indole-1,3,4-thiadiazole derivatives (<strong>10a–j</strong>) is synthesized. The in vitro anticancer properties of newly developed compounds <strong>10a–j</strong> were investigated against four human cancer cell lines like MCF-7 (breast cancer), A549 (lung cancer), Colo-205 (colon cancer) and A2780 (ovarian cancer) by employing of MTT assay. The obtained IC<sub>50</sub> value was compared with etoposide which was used as positive control. The promising IC<sub>50</sub> values of compounds 11.6 ± 8.54 µM, 3.34 ± 0.152 µM. Among the synthesized compounds, three compounds <strong>10a, 10b</strong> and <strong>10c</strong> displayed more cytotoxic activity than positive control.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 2","pages":"Pages 138-145"},"PeriodicalIF":1.8,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129701","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}
引用次数: 0
Synthesis of novel benzimidazole-based retrochalcones and their anticancer activity against breast and colon cancer 新型苯并咪唑类后查尔酮的合成及其对乳腺癌和结肠癌的抗癌作用
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-17 DOI: 10.1080/00397911.2024.2440026
Aboudramane Koné , Coulibaly Souleymane , Mabintou Kalo , Camara Tchambaga Etienne , Sylvain Collet , Drissa Sissouma
{"title":"Synthesis of novel benzimidazole-based retrochalcones and their anticancer activity against breast and colon cancer","authors":"Aboudramane Koné ,&nbsp;Coulibaly Souleymane ,&nbsp;Mabintou Kalo ,&nbsp;Camara Tchambaga Etienne ,&nbsp;Sylvain Collet ,&nbsp;Drissa Sissouma","doi":"10.1080/00397911.2024.2440026","DOIUrl":"10.1080/00397911.2024.2440026","url":null,"abstract":"<div><div>A series of novel 3-benzimidazolyl retrochalcones (<strong>6a–g</strong>) was synthesized and evaluated for their anticancer activities against breast (MDA-MB-231, MCF-7) and human colon (Caco-2, HCT-116) cancer cell lines. The compounds demonstrated significant anticancer potential, with compound <strong>6d</strong> exhibiting the most potent activity (IC<sub>50</sub> &lt; 1.56 μM) across all tested cell lines. Most compounds were more active than Roscovitine but less potent than Paclitaxel (Taxol<sup>®</sup>). Notably, compound <strong>6e</strong> was inactive against both Caco-2 and MDA-MB-231 cell lines. The presence of electron-donating methoxy groups enhanced anticancer efficacy, while electron-withdrawing nitro groups had a detrimental effect. The high amplitude values (70%–98%) observed for the compounds indicate effective targeting of cancer cells, while lower amplitudes in fibroblasts (27%–49%) suggest selective antimitotic effects. These findings highlight the potential of benzimidazole-supported retrochalcones as promising candidates for further development as broad anticancer agents.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 2","pages":"Pages 175-182"},"PeriodicalIF":1.8,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129705","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}
引用次数: 0
An efficient synthesis of some new bipyrazole derivatives by three-component reaction between 3-methyl-1H-pyrazol-4(5H)-one, aroylphenylhydrazones and arylglyoxals 用3-甲基- 1h -吡唑-4(5H)- 1、芳基苯基腙和芳基乙二醛三组分反应高效合成了一些新的联吡唑衍生物
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-17 DOI: 10.1080/00397911.2024.2431990
Maryam Oudi , Mohammad Anary-Abbasinejad
{"title":"An efficient synthesis of some new bipyrazole derivatives by three-component reaction between 3-methyl-1H-pyrazol-4(5H)-one, aroylphenylhydrazones and arylglyoxals","authors":"Maryam Oudi ,&nbsp;Mohammad Anary-Abbasinejad","doi":"10.1080/00397911.2024.2431990","DOIUrl":"10.1080/00397911.2024.2431990","url":null,"abstract":"<div><div>A simple one-pot and catalyst-free method is reported for synthesis of some new bipyrazole derivatives by three-component reaction between arylglyoxals, 3-methyl-1<em>H</em>-pyrazol-4(5<em>H</em>)-one and aroylphenylhydrazone derivatives. The reactions were carried out in ethanol as a green solvent in neutral reaction conditions and products were simply isolated by filtering of the precipitated solids in high yields. All products were characterized by their <sup>1</sup>H and <sup>13</sup>C NMR and IR spectral and elemental analysis data.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 2","pages":"Pages 146-151"},"PeriodicalIF":1.8,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129704","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}
引用次数: 0
Green and sustainable synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones via the Biginelli reaction using L-arabinose as a renewable catalyst under solvent-free conditions 在无溶剂条件下，以l -阿拉伯糖为可再生催化剂，通过Biginelli反应绿色可持续合成3,4-二氢嘧啶-2(1H)-酮/硫酮
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-17 DOI: 10.1080/00397911.2024.2435463
Priya C. Saroj , Sai Srinivas Ponugoti , Shivangi Sawant , Shreerang V. Joshi
{"title":"Green and sustainable synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones via the Biginelli reaction using L-arabinose as a renewable catalyst under solvent-free conditions","authors":"Priya C. Saroj ,&nbsp;Sai Srinivas Ponugoti ,&nbsp;Shivangi Sawant ,&nbsp;Shreerang V. Joshi","doi":"10.1080/00397911.2024.2435463","DOIUrl":"10.1080/00397911.2024.2435463","url":null,"abstract":"<div><div>In the pursuit of sustainable methodologies in organic synthesis, the application of renewable and biodegradable catalysts has received significant attention. This work processes the synthesizing of 3,4-dihydropyrimidin-2(1H)-ones/thiones using L-arabinose, an environment-friendly catalyst <em>via</em> the Biginelli reaction in a solvent-free environment is reported herein. L-arabinose, a naturally occurring sugar, efficiently catalyzes the condensation reaction between β-ketoesters and aldehyde with urea or thiourea to form DHPMs with high yields and excellent atom economy. The reaction proceeds efficiently at mild temperatures, and the catalyst is easily regenerated, enabling multiple catalytic cycles. The use of L-arabinose avoids not only toxic solvents and metal catalysts but also processes green chemistry due to the exploitation of renewable resources. It is a significant step forward in the domain of sustainable catalysis and provides an environmentally benign and operationally simple procedure for the synthesis of DHPMs.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 2","pages":"Pages 152-165"},"PeriodicalIF":1.8,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129703","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}
引用次数: 0
Synthesis and characterization of new isatin hybrids based on isatin-coumarin hybrid as potent antioxidant, anti-inflammatory and antimicrobial agents 以isatin-香豆素为基础的isatin-coumarin复合物的合成与表征
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-17 DOI: 10.1080/00397911.2024.2431029
Omyma A. Abd Allah , Ehab S. M. Elkhayat , Amr H. Moustafa , Alaa A. Fahmy
{"title":"Synthesis and characterization of new isatin hybrids based on isatin-coumarin hybrid as potent antioxidant, anti-inflammatory and antimicrobial agents","authors":"Omyma A. Abd Allah ,&nbsp;Ehab S. M. Elkhayat ,&nbsp;Amr H. Moustafa ,&nbsp;Alaa A. Fahmy","doi":"10.1080/00397911.2024.2431029","DOIUrl":"10.1080/00397911.2024.2431029","url":null,"abstract":"<div><div>Iisatin hybrids have emerged as effective weapons against diseases. In this context, chalcone tethered isatin-coumarin hybrid <strong>3</strong> was synthesized and used as a building block for the preparation of a new series of isatin-pyrazole, isatin-bridged dibenzo-diazonin and isatin-coumarin hybrids <strong>4–10</strong> by reaction with ammonium acetate or primary aromatic amines. The hybrids <strong>4–10</strong> were linked with bioactive linkers named ethene, furan, pyrrole or its derivatives. Through another reaction route, the polyfused pyrano-indoles <strong>11–13</strong> were synthesized by one pot reaction of isatin - coumarin hybrid <strong>3</strong> with some primary amines having electron donating substituents. The chemical structures of the synthesized compounds were evaluated by infrared, nuclear magnetic resonance, MS and elemental analyses. The synthesized compounds were screened for their antioxidant, anti-inflammatory and antimicrobial effects. The results revealed that all the compounds have high antioxidant activity and some of these compounds provide anti-inflammatory effects close to that of indomethacin. While the antimicrobial effects were studied against both Gram - positive and Gram-negative bacteria, greater activity for compounds <strong>3</strong> and <strong>6</strong> was observed against Gram-positive bacteria (<em>B. Subtilis</em>). While compounds <strong>3, 4, 6, 9</strong> and <strong>10</strong> were active against Gram-negative bacteria (<em>E. coli</em>).</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 2","pages":"Pages 116-137"},"PeriodicalIF":1.8,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129702","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}
引用次数: 0
A linear approach for the total synthesis of sex pheromone (3S, 5R, 6S)-6-isopropyl-3,5-dimethyltetrahydro-2H-pyran-2-one and prelactone B 全合成性信息素(3S, 5R, 6S)-6-异丙基-3,5-二甲基四氢- 2h -吡喃-2-酮和预内酯B的线性方法
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-11 DOI: 10.1080/00397911.2025.2449591
Manohar Surve , Naresh Gantasala , Sudheer Pudi , Srihari Pabbaraja
{"title":"A linear approach for the total synthesis of sex pheromone (3S, 5R, 6S)-6-isopropyl-3,5-dimethyltetrahydro-2H-pyran-2-one and prelactone B","authors":"Manohar Surve ,&nbsp;Naresh Gantasala ,&nbsp;Sudheer Pudi ,&nbsp;Srihari Pabbaraja","doi":"10.1080/00397911.2025.2449591","DOIUrl":"10.1080/00397911.2025.2449591","url":null,"abstract":"<div><div>A linear 10-step approach for the stereoselective total synthesis of (3<em>S</em>,5<em>R</em>,6<em>S</em>)-6-isopropyl-3,5-dimethyltetrahydro-2<em>H</em>-pyran-2-one, the sex pheromone component of <em>Macrocentrus grandii</em> is presented. The key steps involve an enantioselective cross Aldol reaction between isobutyraldehyde and propionaldehyde, a chiral auxiliary mediated diastereoselective methylation reaction, chemoselective reduction of α,β-unsaturated ester and chemoselective oxidation reaction to get lactone. A similar strategy has been applied for the total synthesis of prelactone B.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 4","pages":"Pages 305-314"},"PeriodicalIF":1.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143378071","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}
引用次数: 0
Advancements in biocatalysis: A comprehensive review of applications in organic synthesis 生物催化的新进展：在有机合成中的应用综述
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-09 DOI: 10.1080/00397911.2024.2449258
Vasavi Nayak , Deepika D , Glanish Jude Martis , Santosh L. Gaonkar
{"title":"Advancements in biocatalysis: A comprehensive review of applications in organic synthesis","authors":"Vasavi Nayak ,&nbsp;Deepika D ,&nbsp;Glanish Jude Martis ,&nbsp;Santosh L. Gaonkar","doi":"10.1080/00397911.2024.2449258","DOIUrl":"10.1080/00397911.2024.2449258","url":null,"abstract":"<div><div>Biocatalysis is an essential tool in the green synthesis of compounds. These catalysts exhibit regioselectivity and stereoselectivity toward specific products, enabling nontoxic and eco-friendly synthetic routes with high-yield biotransformation and enantioselectivity, resulting in enantiopure products. Moreover, the <em>E</em>-factor, which measures the efficiency of a process by calculating the ratio of waste generated to the product formed, is significantly lower in biocatalytic organic synthesis than in traditional methods. The reusability of biocatalysts allows for economically advantageous designs, enabling the reproducibility of products with better yields and energy efficiency in the synthetic route. In this context, enzymes and their modified counterparts have been emphasized as biocatalysts for the biotransformation and asymmetric bio-reduction of various ketones, aldehydes, esters, alcohols, and other substrates.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 6","pages":"Pages 443-464"},"PeriodicalIF":1.8,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143521107","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}
引用次数: 0
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