An Efficient Aromatization of 2-Amino-4,5,6,7-tetrahydrobenzo-[b]thiophene-3-carboxylates in Dimethyl Sulfoxide Catalyzed by p-Toluenesulfonic Acid

被引：21

作者：

Adib, Mehdi ^{[1
]}

Soheilizad, Mehd ^{[1
]}

Rajai-daryasaraei, Saideh ^{[1
]}

Mirzaei, Peiman ^{[2
]}

机构：

[1] Univ Tehran, Coll Sci, Sch Chem, Tehran, Iran

[2] Shahid Beheshti Univ, Dept Chem, Tehran, Iran

来源：

SYNLETT | 2015年 / 26卷 / 08期

关键词：

2-aminobenzo[b]thiophene-3-carboxylates; Gewald reaction; oxidation-aromatization; dimethyl sulfoxide; p-toluenesulfonic acid; ESTROGEN-RECEPTOR MODULATORS; BIOLOGICAL EVALUATION; BENZOTHIOPHENE; DERIVATIVES; LIGANDS; ARZOXIFENE; INHIBITORS; THIOPHENE; AGENTS;

D O I：

10.1055/s-0034-1379998

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

A novel oxidation-aromatization of alkyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates is reported. The Gewald product, obtained from three-component condensation reaction between a cyclohexanone, an alkyl cyanoacetate, and sulfur, underwent an oxidation reaction in dimethyl sulfoxide in the presence of a catalytic amount of p-toluenesulfonic acid to give the corresponding alkyl 2-aminobenzo[b]thiophene-3-carboxylate in excellent yield.

引用

收藏

页码：1101 / 1105

页数：5

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