Synthesis of 2-(arylthio)benzoates by [3+3] cyclocondensations of 3-arylthio-1-silyloxy-1,3-butadienes with 3-oxo-orthoesters, 1,1,3,3-tetramethoxypropane and 1,1-bis(methylthio)-1-en-3-ones

被引：4

作者：

Imran, Muhammad ^{[1
]}

Iqbal, Inam ^{[1
]}

Rasool, Nasir ^{[1
,3
]}

Fischer, Christine ^{[2
]}

Langer, Peter ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

[3] GC Univ Faisalabad, Dept Chem, Faisalabad, Pakistan

来源：

TETRAHEDRON | 2009年 / 65卷 / 43期

关键词：

Arenes; Cyclizations; Diaryl sulfides; Regioselectivity; Silyl enol ethers; DIELS-ALDER REACTIONS; REGIOSELECTIVE SYNTHESIS; DIARYL SULFIDES; ALKYNYL SULFIDES; ARYL HALIDES; CYCLIZATIONS; SULFUR; BENZOPENTATHIEPIN; EFFICIENT; VARACIN;

D O I：

10.1016/j.tet.2009.08.078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of 2-arylthio-4-methoxybenzoates are regioselectively prepared by TiCl4-mediated [3+3] cyclocondensations of 3-arylthio-1-trimethylsilyloxy-1,3-butadienes with 3-oxo-orthoesters. Unsubstituted 2-(arylthio)benzoates were prepared by Me3SiOTf-catalyzecl cyclization of 3-arylthio-1-trimethylsilyloxy-1,3-butadienes with 1,1,3,3-tetramethoxypropane. The TiCl4-mediated cyclization of 3-arylthio-1-trimethylsilyloxy-1,3-butadienes with 1,1-bis(methylthio)-1-en-3-ones results in regioselective formation of 2-arylthio-6-(methylthio)benzoates. (c) 2009 Elsevier Ltd. All rights reserved.

引用

页码：8794 / 8801

页数：8

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