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A Base Promoted [3+2] Cycloaddition of Benzothiazolium Salts with Isoindigos to Synthesis N, S‐polyheterocyclic 3, 3′ Bispirooxindoles
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400478
Chen‐Yi Li , Yao Wang , Dan Hu , Bin Zhang , Heng Yin , Yu‐Long Li
{"title":"A Base Promoted [3+2] Cycloaddition of Benzothiazolium Salts with Isoindigos to Synthesis N, S‐polyheterocyclic 3, 3′ Bispirooxindoles","authors":"Chen‐Yi Li ,&nbsp;Yao Wang ,&nbsp;Dan Hu ,&nbsp;Bin Zhang ,&nbsp;Heng Yin ,&nbsp;Yu‐Long Li","doi":"10.1002/ajoc.202400478","DOIUrl":"10.1002/ajoc.202400478","url":null,"abstract":"<div><div>A base promoted [3+2] cycloaddition of benzothiazolium salts with isoindigos has been developed, and a series of novel N, S‐polyheterocyclic 3, 3′ bispirooxindoles with four contiguous cycles and two spiro quaternary stereocenters have been successfully and effectively prepared in good to excellent yields (up to 99 %) under mild conditions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400478"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143119115","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
Cobalt‐Catalyzed Synthesis of Functionalized Nordazepams and Benzimidazoquinazolines and Their Photophysical Properties
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400455
Sundararajan Suresh , Pari Keerthana , Fazlurrahman Nawaz Khan
{"title":"Cobalt‐Catalyzed Synthesis of Functionalized Nordazepams and Benzimidazoquinazolines and Their Photophysical Properties","authors":"Sundararajan Suresh ,&nbsp;Pari Keerthana ,&nbsp;Fazlurrahman Nawaz Khan","doi":"10.1002/ajoc.202400455","DOIUrl":"10.1002/ajoc.202400455","url":null,"abstract":"<div><div>An efficient and environmentally friendly one‐pot sequential synthesis of functionalized nordazepam and a benzimidazoquinazoline analogue is reported, utilizing cobalt as the metal catalyst. The reaction proceeds <em>via</em> either the <em>α</em>‐alkenylation or dehydrogenative <em>sp</em><sup><em>3</em></sup> C−H functionalization pathway. This transformation includes mild reaction conditions, operational simplicity, and good functional group tolerance. Additionally, this method is suitable for the gram‐scale synthesis of functionalized nordazepam and benzimidazoquinazoline compounds. Furthermore, the synthetic utility, photophysical properties and real‐life application of the synthesized derivatives were explored.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400455"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143121421","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
Synthesis of Spirocyclic‐1,2‐Benzisothiazoles by Rh(III)‐Catalyzed [4+1] Annulation of Sulfoximines with Maleimides
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400537
Anil Kumar , Sudharshan Nagabhushana Reddy , Vinayak Hanchate , Kandikere Ramaiah Prabhu
{"title":"Synthesis of Spirocyclic‐1,2‐Benzisothiazoles by Rh(III)‐Catalyzed [4+1] Annulation of Sulfoximines with Maleimides","authors":"Anil Kumar ,&nbsp;Sudharshan Nagabhushana Reddy ,&nbsp;Vinayak Hanchate ,&nbsp;Kandikere Ramaiah Prabhu","doi":"10.1002/ajoc.202400537","DOIUrl":"10.1002/ajoc.202400537","url":null,"abstract":"<div><div>Rh(III)‐catalyzed spiro‐annulation of sulfoximines with maleimides leads to the diastereoselective synthesis of spirocyclic‐1,2‐benzisothiazole heterocycles is disclosed here. This strategy rapidly assembles five‐membered sulfur‐nitrogen‐containing spirocyclic molecules in one‐step. Moreover, the method is scalable and exhibits favourable diastereoselectivity, moderate functional group tolerance, and excellent site‐selectivity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400537"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143113192","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
Discovery and MD Simulation of a Triterpenoid Zj7 as GR Modulator Targeting Non‐Classical GRE with Potent Anti‐Obesity Activity
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400540
Dr. Yeonghun Song , Junekyoung Lee , Seonghun Kim , Prof. Dr. Seunghee Lee , Prof. Dr. Sanghee Kim
{"title":"Discovery and MD Simulation of a Triterpenoid Zj7 as GR Modulator Targeting Non‐Classical GRE with Potent Anti‐Obesity Activity","authors":"Dr. Yeonghun Song ,&nbsp;Junekyoung Lee ,&nbsp;Seonghun Kim ,&nbsp;Prof. Dr. Seunghee Lee ,&nbsp;Prof. Dr. Sanghee Kim","doi":"10.1002/ajoc.202400540","DOIUrl":"10.1002/ajoc.202400540","url":null,"abstract":"<div><div>Despite the potential of non‐classical glucocorticoid response element (GRE)‐selective glucocorticoid receptor (GR) modulators in biomedical sciences, progress has not yet been made. In this study, we discovered a first‐in‐class chemical modulator that selectively suppresses the transcriptional activity of the GR in a gene with a non‐classical GRE, but not with classical GREs. The orexigenic agouti‐related peptide (<em>Agrp</em>)‐gene with a non‐classical GRE was chosen for this study. Similarity‐implemented virtual screening and rational modification of the structure of the initial hit compounds led to the identification of a pentacyclic natural triterpenoid, Zj7 (2‐<em>O‐trans‐p</em>‐coumaroylalphitolic acid). With this compound, we recently reported the verification of the orexigenic function and mechanism of action of GR in AgRP neurons. Herein, we describe the detailed discovery process leading to the identification of Zj7 and propose its molecular mode of action using molecular dynamics simulation.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400540"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143114145","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
Acid Sensors Based on Luminochromism of Solid‐State Excimer Emission of Pyrene‐Modified Polyhedral Oligomeric Silsesquioxane
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400508
Hayato Narikiyo , Masayuki Gon , Kazuo Tanaka , Yoshiki Chujo
{"title":"Acid Sensors Based on Luminochromism of Solid‐State Excimer Emission of Pyrene‐Modified Polyhedral Oligomeric Silsesquioxane","authors":"Hayato Narikiyo ,&nbsp;Masayuki Gon ,&nbsp;Kazuo Tanaka ,&nbsp;Yoshiki Chujo","doi":"10.1002/ajoc.202400508","DOIUrl":"10.1002/ajoc.202400508","url":null,"abstract":"<div><div>To obtain solid‐state fluorescence sensors, it is essential to simultaneously obtain solid‐state emission and stimuli‐responsiveness. In this research, the modified polyhedral oligomeric silsesquioxane (POSS) tethered with pyrenes was synthesized and we confirmed that both demands for developing solid‐state fluorescence sensors can be satisfied. The POSS derivative exhibited strong emission even in the solid state. In particular, we found that exposure of the POSS films to trifluoroacetic acid vapor resulted in a significant red‐shift of the peak wavelength of the emission band. Excitation spectroscopy and comparison with model compounds suggest that this significant red‐shift should be attributable to the formation of static excimer, meaning a preformed dimer in the ground state induced by protonation of the secondary amino groups. These results indicate that POSS is a promising scaffold for a solid‐state fluorescence sensor.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400508"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143118504","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
Rh(III)‐Catalyzed Annulation of (Het)aryl Amides with α‐Allenyl‐Containing α‐Amino Acid Derivatives
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400476
Daria V. Vorobyeva , Alexandra S. Bubnova , Ivan A. Godovikov , Alexander F. Smol'yakov , Sergey N. Osipov
{"title":"Rh(III)‐Catalyzed Annulation of (Het)aryl Amides with α‐Allenyl‐Containing α‐Amino Acid Derivatives","authors":"Daria V. Vorobyeva ,&nbsp;Alexandra S. Bubnova ,&nbsp;Ivan A. Godovikov ,&nbsp;Alexander F. Smol'yakov ,&nbsp;Sergey N. Osipov","doi":"10.1002/ajoc.202400476","DOIUrl":"10.1002/ajoc.202400476","url":null,"abstract":"<div><div>An efficient pathway to a new series of CF<sub>3</sub>‐substituted α‐amino acid derivatives decorated with pharmacophore isoquinolone and pyrimido[1,6‐<em>a</em>]indolone cores has been developed. The method includes Rh(III)‐catalyzed C−H activation/[4+2]‐annulation of <em>N‐</em>(pivaloyloxy)‐substituted aryl hydroxamates and indole‐1‐carboxamides with readily available allenyl‐containing α‐amino carboxylates and their phosphorus analogues. It was established that the reactions occur <em>via</em> Rh‐σ‐alkenyl intermediates to provide new C−C bond forming process with the participation of terminal carbon atom of allene moiety.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400476"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143120121","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
Recyclable Ag/g‐C3N4 Catalyzed Visible‐light Promoted Heterogeneous Synthesis of Unsymmetric Diaryl Chalcogenides
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400413
Hong‐Tao Ji , Yu‐Tao Yi , Min‐Hang Zhou , Qing‐Xia Luo , Jun Jiang , Wei‐Min He
{"title":"Recyclable Ag/g‐C3N4 Catalyzed Visible‐light Promoted Heterogeneous Synthesis of Unsymmetric Diaryl Chalcogenides","authors":"Hong‐Tao Ji ,&nbsp;Yu‐Tao Yi ,&nbsp;Min‐Hang Zhou ,&nbsp;Qing‐Xia Luo ,&nbsp;Jun Jiang ,&nbsp;Wei‐Min He","doi":"10.1002/ajoc.202400413","DOIUrl":"10.1002/ajoc.202400413","url":null,"abstract":"<div><div>With Ag/g‐C<sub>3</sub>N<sub>4</sub> semiconductor as the heterogeneous photocatalyst, the visible light promoted heterogeneous synthesis of unsymmetric diaryl chalcogenides could be achieved under additive‐free and mild conditions. A series of unsymmetric diaryl chalcogenides were generated in good to excellent yields with high functional group tolerance. The Ag/g‐C<sub>3</sub>N<sub>4</sub> photocatalyst is easily recovered from the reaction mixture and reused at least 5 times, opening the way for larger‐scale industrial applications of this type of photocatalytic bond‐forming reactions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400413"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143120122","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
In Situ Generated 1‐Naphthylmethyl Radicals from Bis(1‐Naphthylmethyl)tin Dichlorides: Utilization for C−C, C−N, and C−O Bond‐Forming Reactions
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400593
Kisturi Dhanwant , Dharmveer Bhedi , M. Bhanuchandra , Ramalingam Thirumoorthi
{"title":"In Situ Generated 1‐Naphthylmethyl Radicals from Bis(1‐Naphthylmethyl)tin Dichlorides: Utilization for C−C, C−N, and C−O Bond‐Forming Reactions","authors":"Kisturi Dhanwant ,&nbsp;Dharmveer Bhedi ,&nbsp;M. Bhanuchandra ,&nbsp;Ramalingam Thirumoorthi","doi":"10.1002/ajoc.202400593","DOIUrl":"10.1002/ajoc.202400593","url":null,"abstract":"<div><div>The in situ‐generated 1‐naphthylmethyl radicals from the thermolysis of bis(1‐naphthylmethyl)tin dichlorides combine with persistent organic radicals, 4‐hydroxy‐TEMPO or 4‐oxo‐TEMPO designs C−O bond forming products. Subsequently, the C−N bond occurs when the 1‐naphthylmethyl radicals unite with nitric oxide (NO) under a nitrogen atmosphere. In contrast, the oxidation instead of the addition reaction predominantly happens in the 1‐naphthylmethyl radicals when nitrogen dioxide contains a high oxidation state nitrogen center, i. e., N(IV) used. The by‐product, dodecanuclear organotin cages, with twelve peripheral naphthyl units, could be isolated from the 4‐hydroxy‐TEMPO reaction. Besides, the synthesis of unsymmetrical diarylmethanes RArCH<sub>2</sub> (R=1‐naphthyl, 2,4,6‐Me<sub>3</sub>C<sub>6</sub>H<sub>2</sub>, 3‐ and 4‐MeC<sub>6</sub>H<sub>4</sub>, phenyl, 4‐ClC<sub>6</sub>H<sub>4</sub>; Ar=4‐MeOC<sub>6</sub>H<sub>4</sub>, 3,4‐, 2,4‐ and 2,5‐Me<sub>2</sub>C<sub>6</sub>H<sub>3</sub>) in high yields and with good regioselectivity is reported. This new methodology involves the iodine‐mediated thermolysis of bis(arylmethyl)tin dichlorides (RCH<sub>2</sub>)<sub>2</sub>SnCl<sub>2</sub> and an excess of an arene. This reaction involves homolytic cleavage of Sn−C bonds to give arylmethyl radicals that react with iodine in the presence of SnCl<sub>2</sub> to give the corresponding cations, which undergo electrophilic attack on the arene. Functionalised diarylmethanes have wide applications in pharmaceutical, agrochemical, and materials sciences. Alternative synthetic approaches to this class of organic compounds that avoid using a transition‐metal catalyst or a strong Lewis acid are desirable.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400593"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143112004","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
Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3+2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400558
Mengcheng Zhang , Yuying Chen , Jiayu Liu , Xiaoyu Yan , Kexin Huang , Xiantao Ma
{"title":"Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3+2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides","authors":"Mengcheng Zhang ,&nbsp;Yuying Chen ,&nbsp;Jiayu Liu ,&nbsp;Xiaoyu Yan ,&nbsp;Kexin Huang ,&nbsp;Xiantao Ma","doi":"10.1002/ajoc.202400558","DOIUrl":"10.1002/ajoc.202400558","url":null,"abstract":"<div><div>We developed a novel method for the synthesis of 2‐substituted‐4,5‐dihydrothiazol‐4‐ols compounds through cyclization of thioamides and 1,4‐dithiane‐2,5‐diol in the presence of Et<sub>3</sub>N. Stable hydroxy‐substituted thiazole compounds were isolated of substituted thioamides. The reaction conditions are simple, the substrate range is wide, and the target compounds were obtained in up to 82 % yield.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400558"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143113935","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
Base‐Catalyzed [4+2] Annulation of Ynones and Acetates for the Synthesis of 2‐Pyrones
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400524
Ting Chen , Moudan Ye , Ting Huang , Zhichao Chen , Jinhai Shen
{"title":"Base‐Catalyzed [4+2] Annulation of Ynones and Acetates for the Synthesis of 2‐Pyrones","authors":"Ting Chen ,&nbsp;Moudan Ye ,&nbsp;Ting Huang ,&nbsp;Zhichao Chen ,&nbsp;Jinhai Shen","doi":"10.1002/ajoc.202400524","DOIUrl":"10.1002/ajoc.202400524","url":null,"abstract":"<div><div>An efficient, practical, and scalable Cs<sub>2</sub>CO<sub>3</sub>‐catalyzed [4+2] annulation reaction between ynones and acetates is presented, wherein ynones serve as the four‐atom annulation partners. This methodology facilitates the synthesis of substituted 2‐pyrones with yields ranging from good to excellent. The ready availability of the starting materials, coupled with the simplicity of the annulation protocol, renders this approach highly amenable to the preparation of a diverse range of 2‐pyrones. Furthermore, the feasibility of the reaction on a gram scale and its application in the synthesis of a potent and selective cyclooxygenase‐2 inhibitor underscore the practical significance and utility of this method.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400524"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143120712","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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