吲哚-2- carboxamides与MBH碳酸盐定向基团控制区域选择性[4 + 3]环化向高取代吲哚-1,2-融合地氮酮

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-04-11 DOI:10.1021/acs.joc.5c0033510.1021/acs.joc.5c00335

Shutao Wang, Wenyao Zhang, Zhuoqi Zhang, Jinbao Xiang* and Lianyou Zheng*,

{"title":"吲哚-2- carboxamides与MBH碳酸盐定向基团控制区域选择性[4 + 3]环化向高取代吲哚-1,2-融合地氮酮","authors":"Shutao Wang, Wenyao Zhang, Zhuoqi Zhang, Jinbao Xiang* and Lianyou Zheng*, ","doi":"10.1021/acs.joc.5c0033510.1021/acs.joc.5c00335","DOIUrl":null,"url":null,"abstract":"A Lewis base-catalyzed [4 + 3] annulation between dinucleophilic indole-2-carboxamides and Morita–Baylis–Hillmann (MBH) carbonates was developed to access densely substituted indole-1,2-fused diazepanones. This reaction is initiated by a Lewis base-catalyzed N-allylic alkylation of the indole scaffold with MBH carbonates, followed by intramolecular Michael cyclization. Notably, the selectivity of this process is controlled by a removable o-methoxyphenyl (OMP) directing group attached to the indole-2-carboxamides. The wide scope of substrates, high regio- and stereoselectivity, and diverse transformations highlight the potential synthetic utility of this method in drug discovery.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 16","pages":"5651–5661 5651–5661"},"PeriodicalIF":3.6000,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Directing Group-Controlled Regioselective [4 + 3] Annulation of Indole-2-Carboxamides with MBH Carbonates toward Highly Substituted Indole-1,2-Fused Diazepanones\",\"authors\":\"Shutao Wang, Wenyao Zhang, Zhuoqi Zhang, Jinbao Xiang* and Lianyou Zheng*, \",\"doi\":\"10.1021/acs.joc.5c0033510.1021/acs.joc.5c00335\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A Lewis base-catalyzed [4 + 3] annulation between dinucleophilic indole-2-carboxamides and Morita–Baylis–Hillmann (MBH) carbonates was developed to access densely substituted indole-1,2-fused diazepanones. This reaction is initiated by a Lewis base-catalyzed N-allylic alkylation of the indole scaffold with MBH carbonates, followed by intramolecular Michael cyclization. Notably, the selectivity of this process is controlled by a removable o-methoxyphenyl (OMP) directing group attached to the indole-2-carboxamides. The wide scope of substrates, high regio- and stereoselectivity, and diverse transformations highlight the potential synthetic utility of this method in drug discovery.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"90 16\",\"pages\":\"5651–5661 5651–5661\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-04-11\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.5c00335\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.5c00335","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

在二亲核吲哚-2-羧酰胺和森田-贝里斯-希尔曼（MBH）碳酸盐之间建立了路易斯碱催化的[4 + 3]环反应，以获得密集取代的吲哚-1,2-融合的二氮杂酮。该反应由Lewis碱催化的吲哚支架与MBH碳酸盐的n -烯丙基烷基化引发，然后是分子内的Michael环化。值得注意的是，该过程的选择性是由附着在吲哚-2-羧酰胺上的可移动的邻甲氧基（OMP）导向基团控制的。底物范围广，区域选择性和立体选择性高，转化多样，突出了该方法在药物发现中的潜在合成用途。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Directing Group-Controlled Regioselective [4 + 3] Annulation of Indole-2-Carboxamides with MBH Carbonates toward Highly Substituted Indole-1,2-Fused Diazepanones

查看原文本刊更多论文

Directing Group-Controlled Regioselective [4 + 3] Annulation of Indole-2-Carboxamides with MBH Carbonates toward Highly Substituted Indole-1,2-Fused Diazepanones

A Lewis base-catalyzed [4 + 3] annulation between dinucleophilic indole-2-carboxamides and Morita–Baylis–Hillmann (MBH) carbonates was developed to access densely substituted indole-1,2-fused diazepanones. This reaction is initiated by a Lewis base-catalyzed N-allylic alkylation of the indole scaffold with MBH carbonates, followed by intramolecular Michael cyclization. Notably, the selectivity of this process is controlled by a removable o-methoxyphenyl (OMP) directing group attached to the indole-2-carboxamides. The wide scope of substrates, high regio- and stereoselectivity, and diverse transformations highlight the potential synthetic utility of this method in drug discovery.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.