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


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.


Pyrimidine Thiourea Guanidine Dimethylformamide Acridine 
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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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