Silver-Promoted (4 + 1) Annulation of Isocyanoacetates with Alkylpyridinium Salts: Divergent Regioselective Synthesis of 1,2-Disubstituted Indolizines,Organic Letters

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Silver-Promoted (4 + 1) Annulation of Isocyanoacetates with Alkylpyridinium Salts: Divergent Regioselective Synthesis of 1,2-Disubstituted Indolizines
Organic Letters ( IF 4.9 ) Pub Date : 2021-09-15 , DOI: 10.1021/acs.orglett.1c02754
Yan Chen ₁ , Andrey Shatskiy ₂ , Jian-Quan Liu _{1,

2} , Markus D Kärkäs ₂ , Xiang-Shan Wang ₁

Affiliation

An unprecedented silver-promoted regioselective (4 + 1) annulation of isocyanoacetates with pyridinium salts is reported. The established protocol provides controlled, facile, and modular access to a range of synthetically useful N-fused heterocyclic scaffolds containing indolizines, pyrrolo[1,2-a]quinolines, pyrrolo[2,1-a]isoquinolines, and 1H-imidazo[4,5-a]indolizin-2(3H)-ones. A mechanistic pathway involving nucleophilic addition/protonation/elimination/cycloisomerization is proposed.

中文翻译：

银促进 (4 + 1) 异氰乙酸酯与烷基吡啶盐的环化：1,2-二取代吲哚嗪的不同区域选择性合成

报道了一种前所未有的银促进的区域选择性 (4 + 1) 异氰乙酸酯与吡啶盐的环化。已建立的协议提供对一系列合成有用的 N-稠合杂环支架的受控、简便和模块化访问，这些支架包含吲哚嗪、吡咯并 [1,2- a ] 喹啉、吡咯并 [2,1- a ] 异喹啉和 1 H -咪唑[4,5 - a ]indolizin-2(3 H )-ones。提出了涉及亲核加成/质子化/消除/环异构化的机制途径。

更新日期：2021-10-01

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