Lawesson's reagent-initiated domino reaction of aminopropenoyl cyclopropanes: synthesis of thieno[3,2-c]pyridinones

被引：12
|
作者：
Huang, Peng [1 ]
Zhang, Rui [1 ]
Liang, Yongjiu [1 ]
Dong, Dewen [1 ]
机构：
[1] Chinese Acad Sci, Changchun Inst Appl Chem, Changchun 130022, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 08期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; RING-OPENING/RECYCLIZATION REACTIONS; SUBSTITUTED PYRIDINE-2,4(1H,3H)-DIONES; HETEROCYCLIC ENAMINONITRILES; DIVERGENT SYNTHESIS; FACILE SYNTHESIS; INHIBITORS; EFFICIENT; TICLOPIDINE; CHEMISTRY;
D O I：
10.1039/c2ob06709a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient and efficient synthesis of substituted 2,3-dihydrothieno[3,2-c]pyridin-4(5H)-ones has been developed and relies upon a domino reaction of dimethylaminopropenoyl cyclopropanes initiated by Lawesson's reagent. A mechanism involving regioselective thionation, ring-enlargement, and an intramolecular aza-cyclization sequence is proposed. This protocol was utilized as a one-pot route to thieno[3,2-c] pyridin-4(5H)-ones with DDQ as an oxidant.
引用
收藏
页码：1639 / 1644
页数：6
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