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

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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.

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Authors and Affiliations

  1. Yuriy Fedkovych Chernivtsi National University, Lesya Ukrainka str. 25, Chernivtsi, 58012, Ukraine

    O. V. Elenich, O. V. Skripskaya, O. S. Lyavinets & P. I. Yagodinets

  2. Ivan Franko National University of Lviv, Kyryla i Mefodiya str. 6, Lviv, 79005, Ukraine

    R. Z. Lytvyn, Kh. E. Pitkovych & M. D. Obushak

Authors
  1. O. V. Elenich
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  2. R. Z. Lytvyn
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  3. O. V. Skripskaya
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  4. O. S. Lyavinets
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  5. Kh. E. Pitkovych
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  6. P. I. Yagodinets
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  7. M. D. Obushak
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Correspondence to O. V. Elenich.

Additional information

Original Russian Text © O.V. Elenich, R.Z. Lytvyn, O.V. Skripskaya, O.S. Lyavinets, Kh.E. Pitkovych, P.I. Yagodinets, M.D. Obushak, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 3, pp. 394–399.

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Elenich, O.V., Lytvyn, R.Z., Skripskaya, O.V. et al. Synthesis of nitrogen-containing heterocycles on the basis of 3-(4-acetylphenyl)-1-methylquinolin-2(1H)-one. Russ J Org Chem 52, 373–378 (2016). https://doi.org/10.1134/S1070428016030131

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  • DOI: https://doi.org/10.1134/S1070428016030131

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