SYNTHESIS OF 2H-BENZO[b]THIETES BY TFA-MEDIATED CYCLIZATION OF O-tert-BUTYL S-(2-VINYLPHENYL) CARBONOTHIOATES VIA 4H-3,1-BENZOXATHIIN-2-ONE INTERMEDIATES

被引：1

作者：

Kobayashi, Kazuhiro ^{[1
,2
]}

Ueyama, Takuma ^{[1
]}

机构：

[1] Tottori Univ, Grad Sch Sustainabil Sci, Dept Engn, Appl Chem Field Chem & Biotechnol Course, 4-101 Koyama Minami, Tottori 6808552, Japan

[2] Tottori Univ, Ctr Res Green Sustainable Chem, 4-101 Koyama Minami, Tottori 6808552, Japan

来源：

HETEROCYCLES | 2019年 / 98卷 / 01期

关键词：

CYCLOADDITION REACTIONS; HYDRIODIC ACID; THIOQUINONE METHIDE; DERIVATIVES; IODINE; BENZYNE;

D O I：

10.3987/COM-18-14021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the preparation of 2H-benzo[b]thiete derivatives under mild conditions has been developed. The reaction of 2-(1-arylethenyl)phenyl bromides with butyllithium at -78 degrees C generates 2-(1-arylethenyl)phenyllithiums, which are successively treated with sulfur and Boc(2)O at the same temperature to afford S-[2-(1-arylethenyl)phenyl] O-tert-butyl carbonothioates. These compounds are then treated with TFA at 0 or 20 degrees C to yield 2-aryl-2-methyl-2H-benzo[b]thietes via formation of the 4-aryl-4-methyl-4H-3,1-benzoxathiin-2-ones followed by decarboxylation.

引用

页码：126 / 135

页数：10