4.4 Article

Molecular iodine-mediated S-N and C-N cross-coupling and oxidative aromatization of 3,4-dihydropyrimidin-2(1H)-thiones with secondary amines

Journal

TETRAHEDRON LETTERS
Volume 54, Issue 14, Pages 1884-1887

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.01.113

Keywords

C2-Functionalized pyrimidines; Oxidative aromatization; 3,4-Dihydropyrimidin-2(1H)-ones; S-N coupling; C-N coupling

Funding

  1. National Nature Science Foundation of China [20902073, 21062017]
  2. Northwest Normal University [nwnu-kjcxgc-03-64]

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A domino S-N and C-N coupling/oxidative aromatization process to synthesize 2-aminothio-phenylpyrimidines and 2-amino-phenylpyrimidines by S-N and C-N cross-coupling reactions is described. This methodology couples 3,4-dihydropyrimidine-2-thiones and secondary amines catalyzed by molecular iodine. Remarkably the C-N coupled product was obtained via a desulfitative coupling-aromatization reaction in one-pot reaction. (C) 2013 Elsevier Ltd. All rights reserved.

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