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Synlett 2013; 24(1): 73-78
DOI: 10.1055/s-0032-1317703
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Indolo[2,3-c]quinolin-6-ones by Sequential Photocyclizations of 3-(2-Azidophenyl)-N-phenylacrylamides

Zhanshan Li
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China   Fax: +86(931)8625657   Email: zhangwei6275@lzu.edu.cn
,
Weixia Wang
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China   Fax: +86(931)8625657   Email: zhangwei6275@lzu.edu.cn
,
Xiaotian Zhang
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China   Fax: +86(931)8625657   Email: zhangwei6275@lzu.edu.cn
,
Congcong Hu
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China   Fax: +86(931)8625657   Email: zhangwei6275@lzu.edu.cn
,
Wei Zhang*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China   Fax: +86(931)8625657   Email: zhangwei6275@lzu.edu.cn
› Author Affiliations
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Publication History

Received: 19 September 2012

Accepted after revision: 05 November 2012

Publication Date:
05 December 2012 (online)

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Abstract

A one-pot synthesis of indolo[2,3-c]quinolin-6(7H)-ones was achieved by sequential photocyclizations of 3-(2-azidophenyl)-N-phenylacrylamides in moderate to high yields. The reactions proceeded via photochemical cyclization of aryl azides to form N-phenylindol-2-carbamides and subsequent 6π-electrocyclic reaction and oxidative aromatization to afford the corresponding indolo[2,3-c]quinolin-6(7H)-ones.

Key words

indolo[2,3-c]quinolin-6(7H)-ones - photocyclization - 3-(2-azidophenyl)-N-phenylacrylamides - aryl azides - 6π-electrocyclic reaction

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
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  • References and Notes

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