SYNTHESIS AND REACTIVITY OF METHYL 3-ACYL-6-AMINO-4-ARYL-5-CYANO-4<i>H</i>-PYRAN-2-CARBOXYLATES

Authors

  • В. П. Шевердов Chuvashia State University named after I. N. Ulyanov
  • А. Ю. Андреев Chuvashia State University named after I. N. Ulyanov
  • О. В. Ершов Chuvashia State University named after I. N. Ulyanov
  • О. Е. Насакин Chuvashia State University named after I. N. Ulyanov
  • В. А. Тафеенко M. V. Lomonosov Moscow State University
  • В. Л. Гейн 3Perm' State Pharmaceutical Academy

DOI:

https://doi.org/10.1007/1114

Keywords:

cyclopentenones, 5-oxopentanoic acid, 4H-pyrans, pyridines, ring opening

Abstract

By treating arylidenemalononitriles with methyl 2,4-dioxobutanoates, derivatives of 4H-pyrans - methyl 3-acyl-6-amino-4-aryl-5-cyano-4H-pyran-2-carboxylates - are obtained, which are novel, promising structural components for the synthesis of carbo- and heterocycles. The reactions of these pyrans with sulfuric and hydrochloric acids, acetic anhydride, and alcohols have been studied. Novel methods have been developed for the preparation of substituted derivatives of cyclopentenone, pyrano[2,3-d]-pyrimidine, 5-oxo-3-phenylpentanoic acid, and nicotinic acid nitrile.

Authors: V. P. Sheverdov, A. Yu. Andreev, O. V. Ershov, O. E. Nasakin, V. A. Tafeenko, and V. L. Gein.

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (7), pp 997-1005

http://link.springer.com/article/10.1007/s10593-012-1091-2

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Published

2013-11-05

Issue

No. 7 (2012)

Section

Original Papers