钢琴-凳子rh -烯醛类烯醛转移：烯醛功能化异喹诺酮类药物的快速构建及其在苯并吩噻啉酮支架中的应用[j]

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-20 DOI:10.1021/acs.orglett.5c0051710.1021/acs.orglett.5c00517

Pratap Kumar Mandal, Sudhir Muduli and Sreenivas Katukojvala*,

{"title":"钢琴-凳子rh -烯醛类烯醛转移：烯醛功能化异喹诺酮类药物的快速构建及其在苯并吩噻啉酮支架中的应用[j]","authors":"Pratap Kumar Mandal, Sudhir Muduli and Sreenivas Katukojvala*, ","doi":"10.1021/acs.orglett.5c0051710.1021/acs.orglett.5c00517","DOIUrl":null,"url":null,"abstract":"Herein, we disclosed a Rh-catalyzed site-selective enal transfer reaction of benzamides with diazoenals leading to multisubstituted enal-functionalized isoquinolone derivatives. The reaction involves arene ortho C–H activation, migratory insertion of a new class of N-heterocyclic Piano-stool Rh-enalcarbenoid, and metal-templated cyclization. The synthetic utility of enal-functionalized isoquinolones has been demonstrated by the short synthesis of valuable benzo[c]phenanthridinone scaffolds, which are present in many naturally occurring alkaloids with broad pharmacological properties and an analogue of oxyavicine natural product used for ophthalmic disorders.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 13","pages":"3231–3236 3231–3236"},"PeriodicalIF":5.0000,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Enal Transfer via Piano-Stool Rh-Enalcarbenoids: Rapid Construction of Enal-Functionalized Isoquinolones, Application Toward Benzo[c]phenanthridinone Scaffolds\",\"authors\":\"Pratap Kumar Mandal, Sudhir Muduli and Sreenivas Katukojvala*, \",\"doi\":\"10.1021/acs.orglett.5c0051710.1021/acs.orglett.5c00517\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Herein, we disclosed a Rh-catalyzed site-selective enal transfer reaction of benzamides with diazoenals leading to multisubstituted enal-functionalized isoquinolone derivatives. The reaction involves arene ortho C–H activation, migratory insertion of a new class of N-heterocyclic Piano-stool Rh-enalcarbenoid, and metal-templated cyclization. The synthetic utility of enal-functionalized isoquinolones has been demonstrated by the short synthesis of valuable benzo[c]phenanthridinone scaffolds, which are present in many naturally occurring alkaloids with broad pharmacological properties and an analogue of oxyavicine natural product used for ophthalmic disorders.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 13\",\"pages\":\"3231–3236 3231–3236\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-03-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.5c00517\",\"RegionNum\":1,\"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":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c00517","RegionNum":1,"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

在此，我们披露了一个铑催化的苯并胺与重氮杂化的位点选择性烯醛转移反应，得到了多取代的烯醛功能化异喹诺酮衍生物。该反应包括芳烃邻位碳氢活化，一类新的n -杂环钢琴-板凳rh -烯醛类化合物的迁移插入，以及金属模板环化。烯醛功能化异喹诺酮类药物的合成用途已被证明是通过短时间合成有价值的苯并[c]菲蒽醌支架，它存在于许多天然存在的生物碱中，具有广泛的药理特性，是用于眼科疾病的天然产物氧维辛的类似物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Enal Transfer via Piano-Stool Rh-Enalcarbenoids: Rapid Construction of Enal-Functionalized Isoquinolones, Application Toward Benzo[c]phenanthridinone Scaffolds

查看原文本刊更多论文

Enal Transfer via Piano-Stool Rh-Enalcarbenoids: Rapid Construction of Enal-Functionalized Isoquinolones, Application Toward Benzo[c]phenanthridinone Scaffolds

Herein, we disclosed a Rh-catalyzed site-selective enal transfer reaction of benzamides with diazoenals leading to multisubstituted enal-functionalized isoquinolone derivatives. The reaction involves arene ortho C–H activation, migratory insertion of a new class of N-heterocyclic Piano-stool Rh-enalcarbenoid, and metal-templated cyclization. The synthetic utility of enal-functionalized isoquinolones has been demonstrated by the short synthesis of valuable benzo[c]phenanthridinone scaffolds, which are present in many naturally occurring alkaloids with broad pharmacological properties and an analogue of oxyavicine natural product used for ophthalmic disorders.

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.