Ionic-liquid-promoted Four-component One-pot Synthesis of Highly Functionalized Benzimidazo[2,1-b][1,3]thiazines: Facile Construction of N-fused Heterocycles

被引：13

作者：

Siddiqui, I. R. ^{[1
]}

Srivastava, Anjali ^{[1
]}

Shamim, Shayna ^{[1
]}

Srivastava, Arjita ^{[1
]}

Shireen ^{[1
]}

Waseem, Malik A. ^{[1
]}

Abumhdi, Afaf A. H. ^{[1
]}

Rahila ^{[1
]}

Srivastava, Anushree ^{[1
]}

Rai, Pragati ^{[1
]}

Singh, R. K. P. ^{[2
]}

机构：

[1] Univ Allahabad, Dept Chem, Lab Green Synth, Allahabad 211002, Uttar Pradesh, India

[2] Univ Allahabad, Dept Chem, Electroorgan & Green Synth Lab, Allahabad 211002, Uttar Pradesh, India

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2卷 / 06期

关键词：

benzimidazo[2,1-b]-[1,3]thiazines; ionic liquids; isocyanides; phenylenediamines; zwitterions; DIVERSITY-ORIENTED SYNTHESIS; MULTICOMPONENT REACTIONS; RING TRANSFORMATION; CHEMISTRY; DERIVATIVES; EFFICIENT; STRATEGY;

D O I：

10.1002/ajoc.201300049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot, four-component, efficient, and facile synthesis of highly functionalized benzimidazo[2,1-b]-[1,3]thiazines promoted by ionic liquid ([bmim]Br)/Et3N has been developed. The protocol involves nucleophilic addition of o-phenylenediamine to carbon disulfide to give 2-mercaptobenzimidazole. After nucleo-philic addition to the activated olefinic bond of a zwitterionic intermediate, which is generated by reaction of isocyanide with an electrophilic alkyne, subsequent cyclization gives benzimidazo[2,1-b][1,3] thiazines with high atom economy. The ionic liquid was recovered and reused without any appreciable decrease in activity and product yield.

引用

页码：519 / 524

页数：6

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