从邻卤代乙炔基苯一锅法合成苯并[b]噻吩和苯并[b]硒吩：制备单、双和三硫属元素并苯的简便方法

One-pot synthesis of benzo[b]thiophenes and benzo[b]selenophenes from o-halo-substituted ethynylbenzenes: convenient approach to mono-, bis-, and tris-chalcogenophene-annulated benzenes.

作者信息

Kashiki Tomoya, Shinamura Shoji, Kohara Masahiro, Miyazaki Eigo, Takimiya Kazuo, Ikeda Masaaki, Kuwabara Hirokazu

机构信息

Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan.

出版信息

Org Lett. 2009 Jun 4;11(11):2473-5. doi: 10.1021/ol900809w.

DOI:10.1021/ol900809w

PMID:19432445

Abstract

A convenient one-pot procedure for the synthesis of benzo[b]thiophenes and selenophenes from readily available o-halo-ethynylbenzene precursors is described. Regardless of the substituent on the acetylene terminus or the number of cyclization moieties on the precursors, various benzo[b]thiophenes and selenophenes, including not only the parent, alkyl-, and phenyl-substituted derivatives but also benzo[1,2-b:4,5-b']dithiophenes and diselenophenes and benzo[1,2-b:3,4-b':5,6-b'']trithiophenes and triselenophenes can be prepared in good to high yields.

摘要

本文描述了一种便捷的一锅法，可从容易获得的邻卤代乙炔基苯前体合成苯并[b]噻吩和硒吩。无论乙炔末端的取代基如何，也无论前体上环化部分的数量多少，各种苯并[b]噻吩和硒吩，不仅包括母体、烷基和苯基取代的衍生物，还包括苯并[1,2-b:4,5-b']二噻吩和二硒吩以及苯并[1,2-b:3,4-b':5,6-b'']三噻吩和三硒吩，都能以良好至高收率制备。