Facile Assembly of 11H-Indolo[3,2-c]quinoline
by a Two-Step Protocol Involving a Regioselective 6-endo-Cyclization Promoted by the Hendrickson Reagent

Min Xu; Qiwen Hou; Shaozhong Wang; Huaqin Wang; Zhu-Jun Yao

doi:10.1055/s-0030-1258411

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Synthesis 2011(4): 626-634
DOI: 10.1055/s-0030-1258411

PAPER

Facile Assembly of 11H-Indolo[3,2-c]quinoline by a Two-Step Protocol Involving a Regioselective 6-endo-Cyclization Promoted by the Hendrickson Reagent

Min Xu^a, Qiwen Hou^a, Shaozhong Wang*^a, Huaqin Wang^b, Zhu-Jun Yao^a
^a School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P. R. of China
Fax: +86(25)83317761; e-Mail: wangsz@nju.edu.cn;
^b Modern Analytical Center of Nanjing University, Nanjing 210093, P. R. of China

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Publication History

Received 1 November 2010
Publication Date:
14 January 2011 (online)

Abstract
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Abstract

An expedient approach was developed to construct the 11H-indolo[3,2-c]quinoline scaffold starting from acyclic alkyne substrates. The five- and six-membered nitrogen-containing rings in the tetracyclic skeleton were elaborated efficiently by gold(III)-catalyzed 5-endo-dig cyclization and Hendrickson reagent promoted regioselective 6-endo cyclization.

Key words

alkyne - cyclization - gold - quinoline - Hendrickson reagent

Reference

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CCDC 780631 and 793932 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.