An Unprecedented and Concise Method for the Synthesis of 1,3-Thiazino-[3,4a][1,3]benzimidazoles via a Three-Component Reaction

被引：13

作者：

Alizadeh, Abdolali ^{[1
]}

Noaparast, Zohreh ^{[1
]}

Sabahnoo, Hamideh ^{[1
]}

Zohreh, Nasrin ^{[1
]}

机构：

[1] Tarbiat Modares Univ, Dept Chem, Tehran 1411713116, Iran

来源：

SYNLETT | 2010年 / 10期

关键词：

benzimidazole; 1,3-thiazine; thiazinobenzimidazole; methyl propiolate; o-phenylenediamine; aryl isothiocyanate; multi-component reaction; ONE-POT SYNTHESIS; MINOR-GROOVE-BINDING; STEREOSELECTIVE-SYNTHESIS; SUBSTITUTED IMIDAZOLINES; DERIVATIVES; ANTIOXIDANT; INHIBITORS; ALKYL;

D O I：

10.1055/s-0029-1219934

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

For the first time, a novel, simple, and highly efficient synthesis of N-aryl-N-[1,3]thiazino[3,4a][1,3]benzimidazol-1ylidenamines is presented. The one-pot reaction of o-phenylenediamine, aryl isothiocyanate, and methyl acetylenecarboxylate proceeds in toluene-dichloromethane without any catalyst under reflux conditions to produce the title compounds in 60-70% yield. From a mechanistic point of view, the reaction is proposed to occur via two cyclizations and four heteroatom-carbon bond formations.

引用

收藏

页码：1469 / 1472

页数：4

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