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.
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.
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DOI：
10.1021/jo102167g
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发表时间：
2011-04
期刊：
影响因子：
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通讯作者：
Ming Li;Zhongmin Zhou;L. Wen;Zhongxuan Qiu
中科院分区：
文献类型：
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作者：
Ming Li;Zhongmin Zhou;L. Wen;Zhongxuan Qiu
具有四个活性中心的2-(2-氯芳酰基)亚甲基咪唑烷具有迷人的结构特征，可作为合成新型杂环化合物的新策略。本文报道了2-(2-氯芳酰基)亚甲基咪唑烷与烯酸酯通过DABCO催化的串联环合反应得到功能化的咪唑(吡啶)[1，2-a]吡啶的新发现。具有特殊意义的是在2-苯甲酰亚甲基咪唑烷的芳环上引入邻卤基，为合成不常见的咪唑(吡啶)[3，2，1-ij][1，8]萘啶提供了一种方便、通用的方法。
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.