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Synthesis 2013; 45(2): 205-218
DOI: 10.1055/s-0032-1316826
DOI: 10.1055/s-0032-1316826
paper
Efficient [5+1] Synthesis of 4-Quinolones by Domino Amination and Conjugate Addition Reactions of 1-(2-Fluorophenyl)prop-2-yn-1-ones with Amines
Further Information
Publication History
Received: 14 September 2012
Accepted after revision: 19 November 2012
Publication Date:
07 December 2012 (online)
Abstract
A catalyst-free synthetic approach is described for the synthesis of 4-quinolone derivatives through a tandem amination/conjugated Michael addition sequence of 1-(2-fluorophenyl)prop-2-yn-1-one derivatives. The [5+1]-cyclization proceeds efficiently at a high temperature under an inert atmosphere with lithium carbonate as a base, and it provides a practical route to a diverse range of 4-quinolones. The mechanism was studied in details and several of the intermediates were isolated.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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