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Synthesis 2010(20): 3536-3544  
DOI: 10.1055/s-0030-1258195
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Route to 1,3-Diazaheterocycle-Fused [1,2-a]Indole Derivatives via Acetic Acid Catalyzed Cyclocondensation Reactions

Li-Juan Yang, Sheng-Jiao Yan, Wen Chen, Jun Lin*
Key Laboratory of Medicinal Chemistry for Natural Resources (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. of China
Fax: +86(871)5033215; e-Mail: linjun@ynu.edu.cn;
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Publication History

Received 7 June 2010
Publication Date:
04 August 2010 (online)

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Abstract

A concise and efficient route for the synthesis of 1,3-diazaheterocycle-fused [1,2-a]indoles by simply refluxing a reaction mixture of different types of heterocyclic ketene aminals and 1,4-benzoquinones catalyzed by acetic acid was developed. This protocol provides an alternative method for application in combinatorial and parallel synthesis in drug discovery.

Key words

1,3-diazaheterocycle-fused [1,2-a]indoles - heterocyclic ketene aminals - 1,4-benzoquinones - catalyst - acetic acid

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1

These authors contributed equally to this paper.

17

CCDC 777124 contains the supplementary crystallographic data for compound 3a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.