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New derivatives of 6-phenylcomanic acid

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Abstract

Ethyl 6-phenylcomanic acid with hydrazine hydrate and hydroxylamine gives 4-oxo-6-phenyl-4H-pyran-2-carbohydrazide and 4-oxo-6-phenyl-4H-pyran-2-carbohydroxamic acid, whereas 6-phenylcomanic acid with ammonia in aqueous DMSO gives 4-hydroxy-6-phenylpicolinic acid, converted further to its ethyl ester and hydrazide. The reaction of 6-phenylcomanic acid with phenylhydrazine gives rise to 3-(1,5-diphenyl-1H-pyrazol-3-yl)-2-(2-phenylhydrazono)propionic acid, which by the Fischer reaction was converted to 3-(1,5-diphenyl-1H-pyrazol-3-yl)-1H-indole-2-carboxylic acid.

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Authors and Affiliations

  1. A. M. Gorky Ural State University, 51 prosp. Lenina, 620083, Ekaterinburg, Russian Federation

    B. I. Usachev, D. L. Obydennov & V. Ya. Sosnovskikh

  2. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620041, Ekaterinburg, Russian Federation

    M. I. Kodess

  3. School of Engineering and Science, Jacobs University of Bremen, P.O. Box 750 561, D-28725, Bremen, Germany

    G. -V. Röschenthaler

Authors
  1. B. I. Usachev
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  2. D. L. Obydennov
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  3. M. I. Kodess
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  4. G. -V. Röschenthaler
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  5. V. Ya. Sosnovskikh
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Correspondence to B. I. Usachev.

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Dedicated to Academician O. N. Chupakhin on the occasion of his 75th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1213–1217, June, 2009.

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Usachev, B.I., Obydennov, D.L., Kodess, M.I. et al. New derivatives of 6-phenylcomanic acid. Russ Chem Bull 58, 1248–1252 (2009). https://doi.org/10.1007/s11172-009-0162-8

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  • DOI: https://doi.org/10.1007/s11172-009-0162-8

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