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Synthesis 2008(9): 1345-1350  
DOI: 10.1055/s-2008-1072532
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Indole Derivatives by Cyclization of Oxo N-Acyliminium Ions

Xiufang Zhenga, Junbiao Chang*a,b, Kang Zhao*a
a School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
b Department of Chemistry, Zhengzhou University, Zhengzou 450001, P. R. of China
Fax: +86(22)27890968; e-Mail: kangzhao@tju.edu.cn;
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Publication History

Received 26 November 2007
Publication Date:
27 March 2008 (online)

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Abstract

The reaction of indole-containing hydroxamates with aldehydes in the presence of Lewis acid leads to oxo N-acyliminium ions, which cyclize to the corresponding N-O fused [1,2]oxazino[4,5-b]indole, [1,2]oxazepino[4,5-b]indole, and [1,2]oxazocino[4,5-b]indole derivatives in good yields.

Key words

oxo N-acyliminium ions - cyclization - hydroxamate - indole - Lewis acid