Synthesis of Polysubstituted Benzo[b][1,5]naphthyridine via Mn(III)-Mediated Domino Cascade Reactions of Cyclopropanols and 2-(2-Isocyanophenyl)acetonitriles

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-02 DOI:10.1021/acs.orglett.4c04097

Shiqiang Mu, Qingqing Xuan, Ying Luo, Yu Guo, Jian Xu, Qiuling Song

引用次数: 0

Abstract

Domino cascade reactions, which can construct multiple bonds in one pot, are efficient methods to synthesize N-heterocycles and other useful skeletons. Herein, we report an expedient synthesis of polysubstituted benzo[b][1,5]naphthyridine via Mn(III)-mediated C–C bond cleavage of cyclopropanols. These reactions were initiated by addition of β-carbonyl radicals, generated from cyclopropyl alcohols in the presence of Mn(III), to 2-(2-isocyanophenyl)acetonitriles to give quinolin-3-amines, which went through intramolecular cyclizations and dehydrogenation to give the final products.

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Mn（III）介导环丙醇和2-（2-异氰苯基）乙腈多米诺级联反应合成多取代苯并[b][1,5]萘啶

多米诺级联反应是合成n -杂环和其他有用骨架的有效方法，它可以在一个锅中构建多个键。本文报道了一种通过Mn（III）介导的环丙醇C-C键裂解合成多取代苯并[b][1,5]萘啶的方法。这些反应是由环丙醇在Mn（III）存在下生成的β-羰基自由基加入到2-（2-异氰苯）乙腈中得到喹啉-3胺，并经过分子内环化和脱氢得到最终产物。

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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.

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