Synthesis of 6H-thieno[3,2-b]pyridin-7-ones from N-(2-X-carbonyl)-3-thienyl ketenimines (X = RS, ArO, R2N) via consecutive [1,5]-X sigmatropic rearrangement and 6π-electrocyclization

被引：4

作者：

Alajarin, Mateo ^{[1
]}

Vidal, Angel ^{[1
]}

Ortin, Maria-Mar ^{[1
]}

机构：

[1] Univ Murcia, Fac Quim, Dept Quim Organ, Murcia 30100, Spain

来源：

SYNTHESIS-STUTTGART | 2007年 / 04期

关键词：

azides; ketenimines; rearrangements; ketenes; thienopyridines;

D O I：

10.1055/s-2007-965874

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(2-X-Carbonyl)-3-thienyl ketenimines (X = RS, ArO, R2N) undergo cyclization under thermal conditions, through a [1,5]X sigmatropic rearrangement followed by a 6 pi-electrocyclic ring closure of the resulting intermediate ketene, to provide 6H-thieno[3,2-b]pyridin-7-ones, bearing alkylthio, arylthio, aryloxy or amino groups at their 5-position.

引用

页码：590 / 596

页数：7