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An Electrochemical Route to Novel N‐benzoyl‐1,2,3‐triazoles and Protein Binding Studies of Selected Triazole Derivatives
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400415
Manas Bandyopadhyay , Upasi Goswami , Shubhankar Ghorai , Swastik Pathak , Debabani Ganguly , Jorge Escorihuela , Jhuma Ganguly , Mrinal K. Bera
{"title":"An Electrochemical Route to Novel N‐benzoyl‐1,2,3‐triazoles and Protein Binding Studies of Selected Triazole Derivatives","authors":"Manas Bandyopadhyay ,&nbsp;Upasi Goswami ,&nbsp;Shubhankar Ghorai ,&nbsp;Swastik Pathak ,&nbsp;Debabani Ganguly ,&nbsp;Jorge Escorihuela ,&nbsp;Jhuma Ganguly ,&nbsp;Mrinal K. Bera","doi":"10.1002/ajoc.202400415","DOIUrl":"10.1002/ajoc.202400415","url":null,"abstract":"<div><div>An electrochemical, cost‐efficient and atom‐economic method for the synthesis of novel, structurally unique N‐benzoyl‐1,2,3‐triazole derivatives has been developed via cascade oxidation‐ 1,3‐dipolar cycloaddition reaction of readily available propargyl alcohol and benzoyl azide. The electro‐oxidation of propargyl alcohol and subsequent cycloaddition was performed in an undivided cell using graphite rod and stainless‐steel plate as inexpensive electrode materials. Numerous 4,5‐disubstituted <em>N</em>‐benzoyl‐1,2,3‐triazoles may be synthesized from milli to multi‐gram scale employing this protocol. The biological significance of few selected triazole derivatives were evaluated via protein binding studies.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400415"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143115020","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}
引用次数: 0
N‐Oxyl Radicals in Oxidative C−O Coupling: Free‐Radical Hydrogen Substitution and Addition to C=C Bonds
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400503
Elena R. Lopat'eva , Dr. Igor B. Krylov , Dr. Bing Yu , Prof. Dr. Alexander O. Terent'ev
{"title":"N‐Oxyl Radicals in Oxidative C−O Coupling: Free‐Radical Hydrogen Substitution and Addition to C=C Bonds","authors":"Elena R. Lopat'eva ,&nbsp;Dr. Igor B. Krylov ,&nbsp;Dr. Bing Yu ,&nbsp;Prof. Dr. Alexander O. Terent'ev","doi":"10.1002/ajoc.202400503","DOIUrl":"10.1002/ajoc.202400503","url":null,"abstract":"<div><div><em>N</em>‐oxyl radicals occupy an important place in free‐radical oxidative CH‐functionalization being one of the most efficient redox‐organocatalysts for hydrogen atom abstraction (HAT). Their applications include aerobic radical chain autoxidation, CH‐functionalization with the formation of carbon‐carbon and carbon‐heteroatom bonds. The persistent nature of <em>N‐</em>oxyl radicals combined with their high reactivity in HAT results in their unique dual chemistry: the same radical can both propagate radical chain reaction (at low <em>N‐</em>oxyl concentrations) and effectively “terminate” carbon‐centered radicals (at higher <em>N‐</em>oxyl concentrations). The latter case opens a new synthetic application area of <em>N‐</em>oxyl radicals, in which they act as both hydrogen abstracting species and O‐reagents for cross‐coupling with carbon‐centered radicals thus produced. Apart from the C−H bond cleavage, reactive <em>N‐</em>oxyl radicals have been extensively used recently in C=C double bond functionalization <em>via</em> radical addition reactions. In this review, both free‐radical CH‐functionalization reactions with the introduction of <em>N‐</em>oxyl fragments and alkene difunctionalizations by <em>N‐</em>oxyls are covered with emphasis on the relationship between reaction conditions and selectivity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400503"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143116452","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}
引用次数: 0
A Facile and Regioselective Synthesis of 2‐Formamidothiazoles via the C−H Formamidation of Thiazole N‐Oxides with Isocyanides
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400321
Yanqiu Zhang , Qianchen Lu , Jiayi Wang , Gonghua Song
{"title":"A Facile and Regioselective Synthesis of 2‐Formamidothiazoles via the C−H Formamidation of Thiazole N‐Oxides with Isocyanides","authors":"Yanqiu Zhang ,&nbsp;Qianchen Lu ,&nbsp;Jiayi Wang ,&nbsp;Gonghua Song","doi":"10.1002/ajoc.202400321","DOIUrl":"10.1002/ajoc.202400321","url":null,"abstract":"<div><div>A facile, microwave‐promoted, regioselective C−H formamidation of thiazole <em>N</em>‐oxides with isocyanides in the presence of TBDPSCl was developed. Various 2‐(<em>N</em>‐substituted formamido)thiazoles were obtained in moderate to high yields. In the case of the C2‐substituted thiazole <em>N</em>‐oxides, the C−H formamidation took place selectively at the C4 position of the thiazole ring. This transformation is also applicable to some other <em>N</em>‐containing heterocyclic derivatives such as pyridine, quinoline, and pyridazine <em>N</em>‐oxides and has advantages such as broad substrate tolerance, high regioselectivity, and mild reaction conditions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400321"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143120265","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}
引用次数: 0
Ligand‐Free Zn Catalyzed Synthesis of Functionalized Indoloacridines
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400482
Nagarajan Sambavi , Prof. Fazlurrahman Nawaz Khan
{"title":"Ligand‐Free Zn Catalyzed Synthesis of Functionalized Indoloacridines","authors":"Nagarajan Sambavi ,&nbsp;Prof. Fazlurrahman Nawaz Khan","doi":"10.1002/ajoc.202400482","DOIUrl":"10.1002/ajoc.202400482","url":null,"abstract":"<div><div>An efficient, ligand‐free, and Zn‐catalyzed dehydrogenation of acridinol/ cyclization of imine product/ dehydrogenative C(sp<sup>3</sup>)‐H functionalization utilizing ChCl‐based deep eutectic solvent system for the assembly of functionalized indoloacridines <strong>9</strong> is reported. The protocol features mild reaction conditions, VOCs free process, broad substrate scope, and applicable gram‐scale synthesis. Furthermore, absorption and solvatochromism properties were explored for the synthesized compounds.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400482"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143113152","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}
引用次数: 0
DFT Study on Copper‐Catalyzed Hydroboration of 1,3‐Diynes: Mechanism, Selectivity, and Comparison with Ruthenium
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400430
Prof. Lei Zhang , Shan Li , Yanhui Wen , Dr. Xiaosi Ma , Dr. Jie Zhang , Prof. Jianguo Zhou , Prof. Xiangtai Meng
{"title":"DFT Study on Copper‐Catalyzed Hydroboration of 1,3‐Diynes: Mechanism, Selectivity, and Comparison with Ruthenium","authors":"Prof. Lei Zhang ,&nbsp;Shan Li ,&nbsp;Yanhui Wen ,&nbsp;Dr. Xiaosi Ma ,&nbsp;Dr. Jie Zhang ,&nbsp;Prof. Jianguo Zhou ,&nbsp;Prof. Xiangtai Meng","doi":"10.1002/ajoc.202400430","DOIUrl":"10.1002/ajoc.202400430","url":null,"abstract":"<div><div>Density functional theory calculations have been performed to explore the mechanism of copper‐catalyzed hydroboration of 1,3‐diyne with HBpin. The catalytic cycles are composed of three elementary processes in succession, namely, the generation of copper hydride species, migratory insertion and σ‐bond metathesis, among which the σ‐bond metathesis step is rate‐determining with a free‐energy barrier of 19.7 kcal/mol. The <em>syn</em>‐addition selectivity originates from the high barrier for converting (<em>Z</em>)‐product to (<em>E</em>)‐product. Effects of diphosphine ligands and substituents on the reactivity were also addressed. Lastly, this copper‐catalyzed hydroboration was compared with a related ruthenium‐catalyzed one, and the obtained results indicated that copper‐catalyzed hydroboration has a more favorable σ‐bond metathesis step and a more challenging migratory insertion step as compared to the ruthenium‐catalyzed counterpart. Wavefunction analyses were performed to understand the observed behaviors.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400430"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143115001","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}
引用次数: 0
Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400456
Sergey S. Grishin , Olga M. Mulina , Leiyang Lv , Vera A. Vil , Zhiping Li , Alexander O. Terent'ev
{"title":"Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles","authors":"Sergey S. Grishin ,&nbsp;Olga M. Mulina ,&nbsp;Leiyang Lv ,&nbsp;Vera A. Vil ,&nbsp;Zhiping Li ,&nbsp;Alexander O. Terent'ev","doi":"10.1002/ajoc.202400456","DOIUrl":"10.1002/ajoc.202400456","url":null,"abstract":"<div><div>The use of C−H compounds as reactive partners in a variety of transformations represents the state of the art in synthetic methodology. In this review, we have summarized the main achievements in using ethers as building blocks for the construction and modification of one of the basic platforms of organic chemistry, nitrogen‐containing heterocycles. Ethers, previously considered mainly as solvents, are excellent CH‐partners, capable of generating radical or cationic reactive species under the action of HAT agents and oxidants. The challenge in this field is the still limited number of heterocyclic systems and other starting reagents, with which the processes can be carried out selectively due to closer bond dissociation energies and oxidation potentials of heterocycles, reactive intermediates and ethers. However, the fine‐tuning of the reaction system using electro‐ and photochemical approaches and a deep understanding of the reaction pathways make the use of ethers as C−H reagents a promising synthetic strategy.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400456"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143115319","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}
引用次数: 0
Integrating Sustainable Chemistry Principles in Polydiacetylene (PDA) Synthesis
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400465
Dr. David Gendron , Dr. Pierre Baillargeon
{"title":"Integrating Sustainable Chemistry Principles in Polydiacetylene (PDA) Synthesis","authors":"Dr. David Gendron ,&nbsp;Dr. Pierre Baillargeon","doi":"10.1002/ajoc.202400465","DOIUrl":"10.1002/ajoc.202400465","url":null,"abstract":"<div><div>Polydiacetylenes (PDAs) represent one of the most intriguing classes of semiconducting polymers, captivating researchers with their unique properties and diverse applications. They possess remarkable electronic and optical characteristics, as well as their ability to undergo dramatic color changes in response to various stimuli. This perspective explores the integration of sustainable chemistry principles into the synthesis of PDAs. We highlight how several elements such as diacetylene green‐coupling synthesis, biodegradability, solid state synthesis and biobased precursors, can contribute to the advancement of more responsible and innovative PDAs materials.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400465"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143117388","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}
引用次数: 0
Recent Advances for Synthesis of Benzothiazoles from Arylmethylamines
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400427
Vikas D. Kadu
{"title":"Recent Advances for Synthesis of Benzothiazoles from Arylmethylamines","authors":"Vikas D. Kadu","doi":"10.1002/ajoc.202400427","DOIUrl":"10.1002/ajoc.202400427","url":null,"abstract":"<div><div>The benzofused <em>N</em>,<em>S</em>‐containing benzothiazole heterocycles and their scaffolds have remarkable biological and pharmaceutical applications. Attentively, the development towards structurally diverse benzothiazoles <em>via</em> C(sp<sup>3</sup>)−<em>H</em> functionalization of arylmethylamines has been the main attraction for synthetic organic chemists. In this review, the various synthetic approaches from C−H/C−N bond functionalization of arylmethylamines/amines as a new emerging substrate are described in detail towards the synthesis of substituted benzothiazoles. Furthermore, it gives insights into substrate scope and the reaction mechanistic pathway for the formation of final targeted benzothiazole products.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400427"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143120120","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}
引用次数: 0
Uncommon Phosphonylation of Pyrazine‐2,3‐dicarbonitrile Derivatives via C(sp2)−CN Bond Cleavage
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400448
Marina V. Volostnykh , Yulia Yu. Enakieva , Gayane A. Kirakosyan , Mikhail S. Grigoriev , Aleksey E. Chufarin , Hailong Wang , Pavel A. Stuzhin , Yulia G. Gorbunova , Aslan Yu. Tsivadze
{"title":"Uncommon Phosphonylation of Pyrazine‐2,3‐dicarbonitrile Derivatives via C(sp2)−CN Bond Cleavage","authors":"Marina V. Volostnykh ,&nbsp;Yulia Yu. Enakieva ,&nbsp;Gayane A. Kirakosyan ,&nbsp;Mikhail S. Grigoriev ,&nbsp;Aleksey E. Chufarin ,&nbsp;Hailong Wang ,&nbsp;Pavel A. Stuzhin ,&nbsp;Yulia G. Gorbunova ,&nbsp;Aslan Yu. Tsivadze","doi":"10.1002/ajoc.202400448","DOIUrl":"10.1002/ajoc.202400448","url":null,"abstract":"<div><div>A direct phosphonylation of the C(sp<sup>2</sup>)−CN bond under mild catalytic and non‐catalytic reaction conditions is disclosed. Pyrazine‐2,3‐dicarbonitriles are readily coupled with HPO(OEt)<sub>2</sub> to produce the corresponding dialkoxyphosphoryl‐substituted pyrazines. The phosphonylation reaction occurs in the presence of a base (Et<sub>3</sub>N, Cs<sub>2</sub>CO<sub>3</sub>) as nucleophilic substitution of the CN groups. The yield of target diphosphonates depends on the nature of substituents in the 5,6‐positions of the pyrazine ring: it exceeds 90 % for di‐5,6‐aryl‐substituted pyrazines and is significantly lower when electron‐donating alkyl (<em>n</em>‐propyl) groups are attached to the 5,6‐positions. It should be noted that for pyrazine‐2,3‐dicarbonitriles bearing vicinal 4‐bromophenyl groups, the nucleophilic phosphonylation leading to C−CN/P−H coupling in the pyrazine ring is predominant over Pd‐catalyzed Hirao's C−Br/P−H coupling reaction in phenyl rings. Detailed structural characterization, both in solution by means of <sup>1</sup>H, <sup>13</sup>C and <sup>31</sup>P NMR spectroscopy and in the solid state by single crystal X‐ray diffraction, of a series of newly synthesized pyrazine phosphonates is reported.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400448"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143114147","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}
引用次数: 0
Site Specific C3‐Alkenylation of Indoles Mediated by In Situ C−H Iodination
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400599
Yongli Zhao , Dingsheng Cao , Prof. Dr. Jie‐Ping Wan , Yunyun Liu
{"title":"Site Specific C3‐Alkenylation of Indoles Mediated by In Situ C−H Iodination","authors":"Yongli Zhao ,&nbsp;Dingsheng Cao ,&nbsp;Prof. Dr. Jie‐Ping Wan ,&nbsp;Yunyun Liu","doi":"10.1002/ajoc.202400599","DOIUrl":"10.1002/ajoc.202400599","url":null,"abstract":"<div><div>The C3‐alkenylation of indoles have been developed by means of a novel <em>in situ</em> iodination tactic which is capable of mediating the Heck coupling with alkenes. The method features specific site‐selectivity oriented by the C−I bond, high‐step efficiency without pre‐functionalization for C‐halogen bond construction, as well as the highly general tolerance to different terminal alkenes, including unactivated alkenes, acrylates, acrylic acid, vinyl sulfone as well as different vinyl functionalized natural products.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400599"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143120267","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}
引用次数: 0
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