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
收藏
页码：590 / 596
页数：7
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