Russian Journal of Organic Chemistry

, Volume 52, Issue 3, pp 373–378 | Cite as

Synthesis of nitrogen-containing heterocycles on the basis of 3-(4-acetylphenyl)-1-methylquinolin-2(1H)-one

  • O. V. ElenichEmail author
  • R. Z. Lytvyn
  • O. V. Skripskaya
  • O. S. Lyavinets
  • Kh. E. Pitkovych
  • P. I. Yagodinets
  • M. D. Obushak


The Meerwein reaction of 1-methylquinolin-2(1H)-one with 4-acetylbenzenediazonium chloride gave 3-(4-acetylphenyl)-1-methylquinolin-2(1H)-one which was brominated to 3-[4-(2-bromoacetyl)phenyl]-1-methylquinolin-2(1H)-one. The latter reacted with pyridine, 4-methylpyridine, quinoline, benzo[f]quinoline, and triphenylphosphine to afford the corresponding quaternary salts, and its reactions with thioacetamide, thiourea, 2-aminopyridine, and 2-aminopyrimidine led to the corresponding thiazole, imidazo[1,2-a]pyridine, and imidazo[1,2-a]pyrimidine derivatives containing a 2-oxoquinoline fragment. 3-(4-{2-[2-(Arylmethylidene)-hydrazinyl]-1,3-thiazol-4-yl}phenyl)-1-methylquinolin-2(1H)-ones were obtained by condensation of 3-[4-(2-bromoacetyl)phenyl]-1-methylquinolin-2(1H)-one with thiosemicarbazide and aromatic aldehydes.


Thioacetamide Phosphonium Salt Oxoethyl Pyridinium Bromide Hydrazinyl 
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

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • O. V. Elenich
    • 1
    Email author
  • R. Z. Lytvyn
    • 2
  • O. V. Skripskaya
    • 1
  • O. S. Lyavinets
    • 1
  • Kh. E. Pitkovych
    • 2
  • P. I. Yagodinets
    • 1
  • M. D. Obushak
    • 2
  1. 1.Yuriy Fedkovych Chernivtsi National UniversityChernivtsiUkraine
  2. 2.Ivan Franko National University of LvivLvivUkraine

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