Literature DB >> 19769334

Three-component synthesis of alpha-branched amines under Barbier-like conditions.

Erwan Le Gall1, Caroline Haurena, Stéphane Sengmany, Thierry Martens, Michel Troupel.   

Abstract

An array of alpha-branched amines has been prepared by using an expedient three-component Mannich-type reaction among organic halides, aldehyde derivatives, and amines. The experimental procedure, which is characterized by its simplicity, employs zinc dust for the in situ generation of organozinc reagents. We show that this Barbier-like protocol constitutes a useful entry to diarylmethylamines, 1,2-diarylethylamines, alpha- or beta-amino esters, benzylamines, and beta-arylethylamines.

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Year:  2009        PMID: 19769334     DOI: 10.1021/jo901704s

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

2.  A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates.

Authors:  Erwan Le Gall; Antoine Pignon; Thierry Martens
Journal:  Beilstein J Org Chem       Date:  2011-07-20       Impact factor: 2.883

3.  A new manganese-mediated, cobalt-catalyzed three-component synthesis of (diarylmethyl)sulfonamides.

Authors:  Antoine Pignon; Erwan Le Gall; Thierry Martens
Journal:  Beilstein J Org Chem       Date:  2014-02-17       Impact factor: 2.883

4.  2-chlorophenyl zinc bromide: a convenient nucleophile for the mannich-related multicomponent synthesis of clopidogrel and ticlopidine.

Authors:  Isabelle Aillaud; Caroline Haurena; Erwan Le Gall; Thierry Martens; Gino Ricci
Journal:  Molecules       Date:  2010-11-11       Impact factor: 4.411

  4 in total

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