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. Elenich
  • R. Z. Lytvyn
  • O. V. Skripskaya
  • O. S. Lyavinets
  • Kh. E. Pitkovych
  • P. I. Yagodinets
  • M. D. Obushak
Article
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Abstract

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.

Keywords

Thioacetamide Phosphonium Salt Oxoethyl Pyridinium Bromide Hydrazinyl 

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Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • O. V. Elenich
    • 1
  • 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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