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Chemistry of Heterocyclic Compounds

, Volume 48, Issue 10, pp 1492–1502 | Cite as

Studies on quinazoline chemistry. 5.* Synthesis of 3,4-dihydroquinazolines with functional substituents at C-2 atom and their alkylation reactions

  • E. V. Gromachevskaya
  • E. A. Kaigorodova
  • K. S. Pushkareva
  • G. D. Krapivin
Article

Syntheses are reported for a new series of 2-substituted 4,4-diphenyl-3,4-dihydroquinazolines by the reaction of o-aminophenyldiphenylcarbinol (APC) with various nitriles. The reaction of APC with substituted 5-bromo-3-cyano-2(1H)-pyridones leads to the formation of derivatives of two products: 3,4-dihydroquinazolines and 4H-3,1-benzoxazines. The alkylation of 3,4-dihydroquinazolines using dimethyl sulfate proceeds through N,N-dimethylation. The structure of these products is a function of the nature of the substituent at C-2 atom of the heterocycle.

Keywords

dimethyl sulfate 4,4-diphenyl-3,4-dihydroquinazolines alkylation mass-spectral fragmentation 

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • E. V. Gromachevskaya
    • 1
  • E. A. Kaigorodova
    • 2
  • K. S. Pushkareva
    • 3
  • G. D. Krapivin
    • 1
  1. 1.Kuban State Technological UniversityKrasnodarRussia
  2. 2.Kuban State Agrarian UniversityKrasnodarRussia
  3. 3.Kuban State UniversityKrasnodarRussia

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