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Synthesis 2013; 45(16): 2328-2336
DOI: 10.1055/s-0033-1339191
DOI: 10.1055/s-0033-1339191
paper
Selective Synthesis of Polysubstituted Dihydroquinolines and α,β-Unsaturated Amidines by a Catalytic Reaction of Ynamides with Ketimines
Further Information
Publication History
Received: 01 May 2013
Accepted after revision: 16 May 2013
Publication Date:
25 June 2013 (online)
Abstract
Ynamides reacted with benzophenone imines in the presence of triflic imide as a catalyst. Ynamides bearing a sulfonamide moiety gave the corresponding 2-amino-3,4-dihydroquinolines selectively in good to high yields. In contrast, yne-carbamates gave the corresponding α,β-unsaturated amidines exclusively. These methods permit simple preparation of sterically crowded polysubstituted quinolines and α,β-unsaturated amidines.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For Diels–Alder reactions of azoquinone methides, see: