Synthesis of Benzimidazole-Fused Medium-Sized N,S-Heterocycles via Palladium-Catalyzed Cyclizations

被引：16

作者：

Lopes, Alexandra Basilio ^{[1
]}

Wagner, Patrick ^{[1
]}

Gulea, Mihaela ^{[1
]}

机构：

[1] Univ Strasbourg, CNRS, Fac Pharm, LIT,UMR 7200, 74 Route Rhin, F-67401 Illkirch Graffenstaden, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 06期

关键词：

Heterocycles; Medium-sized N; S-heterocycles; Benzimidazole; Palladium; Cyclization; COUPLING CASCADE REACTIONS; CHEMICAL SPACE; RING-EXPANSION; EFFICIENT SYNTHESIS; DOMINO REACTIONS; HETEROCYCLES; SULFUR; ACCESS; NITROGEN; ROUTE;

D O I：

10.1002/ejoc.201801686

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of unprecedented benzimidazole-fused thiazocines, thiazonines, and thiazecines having an exocyclic double bond is reported. The process proceeds through an 8-, 9-, or 10-exo-dig cyclocarbopalladation followed by reduction. The scope and limitations were established and showed the importance of the precursor structure for the success of the reaction. A competition between the exo-dig and the endo-dig cyclization was observed for two substrates bearing an N-homopropargyl chain, the endo-cyclization leading to rarely encountered 10- and 11-membered N,S-heterocycles with a trans-endocyclic double bond. X-ray structures of three products were obtained by co-crystallization with fumaric acid and show the twisted structures of these molecules.

引用

页码：1361 / 1370

页数：10

共 69 条

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