Chemistry of Heterocyclic Ketene Aminals: Construction of Imidazo (pyrido)[1,2-a]pyridines and Imidazo(pyrido)[3,2,1-ij][1,8]naphthyridines via DABCO-Catalyzed Tandem Annulations

被引：63

作者：

Li, Ming ^{[1
]}

Zhou, Zhong-Min ^{[1
]}

Wen, Li-Rong ^{[1
]}

Qiu, Zhong-Xuan ^{[1
]}

机构：

[1] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, State Key Lab Base Ecochem Engn, Qingdao 266042, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 09期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; AZA-ENE REACTION; FUSED 1,3-DIAZAHETEROCYCLES; ALLENIC ESTERS; EFFICIENT SYNTHESIS; SYNTHETIC ROUTE; SUBSTITUTED 1,4-DIHYDROPYRIDINES; SALICYLIC ALDEHYDES; BICYCLIC PYRIDONES; MICHAEL ADDITION;

D O I：

10.1021/jo102167g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(2-Chloroaroyl)methyleneimidazolidines with four reactive sites show fascinating structural features and could be used as a new strategy for the synthesis of novel heterocycles. This paper presents our new findings in the reaction of 2-(2-chloroaroyl) methyleneimidazolidines with allenic esters affording functionalized imidazo(pyrido)[1,2-a]pyridines via DABCO-catalyzed tandem annulations. Of particular significance is the incorporation of an o-halo group into the aryl ring of 2-benzoylmethylene-imidazolidines to set up a convenient and general way for constructing unusual imidazo(pyrido)[3,2,1-ij] [1,8]naphthyridines.

引用

页码：3054 / 3063

页数：10

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