Ylide-Induced Ring Contraction of Coumarins to Benzofurans: Applications to the Synthesis of Bis-Heterocycles

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-15 DOI:10.1021/acs.orglett.5c00079

Sandeep Kumar, Dinesh Kumar Gopalakrishnan, Shashank Shrotriya, Tarak Karmakar, Janakiram Vaitla

引用次数: 0

Abstract

We report an unusual ring contraction of 4-chlorocoumarin to benzofuranoyl sulfoxonium ylides using a Corey-ylide. These stabilized ylides were subsequently utilized for the synthesis of various valuable bis-heterocycles under both metal and metal-free conditions. The synthetic utility of this method is illustrated through the synthesis of known bioactive compounds. Detailed mechanistic investigations and quantum chemical calculations have provided valuable insights into the mechanism of the ring contraction reaction.

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Ylide-Induced Ring Contraction of Coumarins to Benzofurans：双杂环合成的应用

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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.