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Synthesis of nitrogen heterocycles underlain by application of 3-(4-Acetyl[phenyl)-2H-coumarin

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Abstract

3-(4-Acetylphenyl)-2H-chromen-2-one was obtained from 4-acetylphenyldiazonium chloride in the conditions of Meerwein reaction. Reactions of 3-[4-(2-bromoacetyl)phenyl]-2H-chromen-2-one with pyridine, 4-methylpyridine, quinoline, benzo[f]quinoline, and triphenylphosphine afforded quaternary salts, and with thioacetamide, thiourea, 2-aminopyridine, 2-aminopyrimidine, and 6-aminopurine provided the corresponding derivatives of thiazole, imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, imidazo[2,1-i]purine. In the reaction of the same bromo derivative with thiosemicarbazide and aromatic aldehydes a thiazole ring is built and the corresponding hydrazones are formed.

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Authors and Affiliations

  1. Yurii Fed’kovich Chernivtsi National University, Chernivtsi, Ukraine

    O. V. Skripskaya, N. O. Feilo, O. V. Elenich & P. I. Yagodinets

  2. Ivan Franko Lviv National University, Lviv, 79005, Ukraine

    A. O. Neshchadin, R. Z. Lytvyn & N. D. Obushak

Authors
  1. O. V. Skripskaya
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  2. N. O. Feilo
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  3. A. O. Neshchadin
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  4. O. V. Elenich
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  5. R. Z. Lytvyn
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  6. N. D. Obushak
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  7. P. I. Yagodinets
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Correspondence to N. D. Obushak.

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Original English Text © O.V. Skripskaya, N.O. Feilo, A.O. Neshchadin, O.V. Elenich, R.Z. Lytvyn, N.D. Obushak, P.I. Yagodinets, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 11, pp. 1673–1678.

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Skripskaya, O.V., Feilo, N.O., Neshchadin, A.O. et al. Synthesis of nitrogen heterocycles underlain by application of 3-(4-Acetyl[phenyl)-2H-coumarin. Russ J Org Chem 49, 1655–1660 (2013). https://doi.org/10.1134/S1070428013110158

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  • DOI: https://doi.org/10.1134/S1070428013110158

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