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Synthesis 1986; 1986(11): 886-891
DOI: 10.1055/s-1986-31817
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Synthesis of 4-Amino-3-pyridinyl and 4-Amino-5-pyrimidinyl Aryl Ketones and Related Compounds via an ortho-Lithiation Reaction

Rumen Radinov* , Marietta Haimova, Ekaterina Simova
  • *Faculty of Chemistry, University of Sofia, 1 Anton Ivanov Ave., 1126 Sofia, Bulgaria
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Publication Date:
20 August 2002 (online)

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4-Chloropyridine and 4,6-dïchloropyrimidine react regioselectively with lithium diisopropylamide to give 4-chloro-3-lithiopyridine and 4,6-dichloro-5-lithiopyrimidine, respectively. These intermediates react with benzaldehydes to give (4-chloro-3-pyridinyl) and 4,6-dichloro-5-pyrimidinyl)-arylmethanols which are oxidized to the corresponding ketones by chromium(VI) oxide in acetone. These compounds ran be nucleophilically substituted with ammonia or primary amines to give 4-amino-3-aroylpyridines or amino-5-aroylpyridines. The 3 aroyl-4-chloropyridines can also be easily converted into 3-aroyl-4(1H)-pyridinones.