The Regiospecific C-Benzylation of Heterocyclic Ketene Aminals with Ethyl 2-(Bromomethyl)benzoate: A Simple Route to 1H-Imidazo[1,2-b][2]benzazepin-5-one Derivatives

Zhan-Hui Xu; Yu-Fei Jie; Mei-Xiang Wang; Zhi-Tang Huang

doi:10.1055/s-2002-20957

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The Regiospecific C-Benzylation of Heterocyclic Ketene Aminals with Ethyl 2-(Bromomethyl)benzoate: A Simple Route to 1H-Imidazo[1,2-b][2]benzazepin-5-one Derivatives

Zhan-Hui Xu, Yu-Fei Jie, Mei-Xiang Wang, Zhi-Tang Huang*
Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Fax: +86(10)62559373; e-Mail: huangzt@public.bta.net.cn;

Abstract

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Abstract

Heterocyclic ketene aminals reacted with ethyl 2-(bromomethyl)benzoate in refluxing acetonitrile to afford the C-benzylated products that underwent intramolecular cyclocondensation reaction to produce ε-lactam fused heterocyclic compounds. The heterocyclic ring size effect on the reaction was discussed.

Key words

heterocyclic ketene aminals - ethyl 2-(bromomethyl)benzoate - 1H-imidazo[1,2-b][2]benzazepin-5-one

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References

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All compounds gave satisfactory elemental analyses C, ±0.33; H, ±0.30; N, ±0.38.