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Chemistry of Heterocyclic Compounds

, Volume 14, Issue 6, pp 653–656 | Cite as

Acetals of lactams and acid amides

XXVI. Syntheses of heterocycles from enamino ketones and enamino amides
  • O. Ya. Belyaeva
  • V. G. Granik
  • R. G. Glushkov
  • T. F. Vlasova
  • O. S. Anisimova
Article
  • 42 Downloads

Abstract

A new approach to the synthesis of one-, two-, and three-ring compounds from enamides and enamino ketones was investigated. Thus the reaction of α-cyano-β-dimethylaminoacrylamide with guanidine gave 2, 4-diamino-5-carbamidopyrimidine, the cyclization of which with dimethylformamide acetal and subsequent hydrolysis gave 2-amino-5,6-dihydro-5-oxopyrimido[4,5-d]pyrimidine. An enamino ketone — 1-benzoyl-2-dimethylamino-2-methylethylene — was subjected to condensation with guanidine, thiourea, and acetamidine, as a result of which 2-substituted 4-phenyl-6-methylpyrimidines were synthesized. The reaction of 1-benzoyl-2-dimethylamino-2-methylethylene with acryloyl chloride leads to 3-dimethylamino-4-benzoyl-Δ2-cyclohexenone, which was converted to the corresponding diethylacetal. A new synthesis of an acridine derivative was realized by reaction of the latter with ethyl anthranilate.

Keywords

Pyrimidine Thiourea Guanidine Dimethylformamide Acridine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • O. Ya. Belyaeva
    • 1
  • V. G. Granik
    • 1
  • R. G. Glushkov
    • 1
  • T. F. Vlasova
    • 1
  • O. S. Anisimova
    • 1
  1. 1.S. Ordzhonikidze All-Union Pharmaceutical-Chemistry InstituteMoscow

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