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
收藏
页码：8794 / 8801
页数：8
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