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Conversions of Coumarins Accompanied by Intermediate Opening and Recyclization of the Lactone Ring. 2. Study of the Interaction of Malonic Acid Hydrazide and Amide Derivatives with 3-Acyl(3-cyano, 3-ethoxycarbonyl)Coumarins
Authors:M. P. Nemeryuk  V. D. Dimitrova  O. S. Anisimova  A. L. Sedov  N. P. Solov'eva  V. F. Traven
Affiliation:(1) D. I. Mendeleev Russian University of Chemical Technology, Moscow, 125047, Russia;(2) Center for Drug Chemistry, All Russian Research Institute of Pharmaceutical Chemistry, Moscow, 119815, Russia
Abstract:Reaction between the N,N′-diisopropylidene and N,N′-diacetyl derivatives of malonic acid dihydrazide and 3-acyl(3-cyano, 3-ethoxycarbonyl)coumarins under the conditions of the Michael reaction lead to the formation of N′-isopropylidene and N′-acetyl derivatives of coumarin-3-carboxylic acid hydrazide. Ethoxycarbonylacethydrazide reacts in an analogous manner. Special features have been studied of the interaction of malonic acid amide derivatives with unsubstituted coumarin and with coumarins containing electron-withdrawing groupings in position 3 of the ring. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1502–1514, October, 2005.
Keywords:3-acyl(3-cyano  3-ethoxycarbonyl)coumarins  malonic acid hydrazide and amide derivatives  mass spectrometric study of reaction products and reaction mixtures  opening and recyclization of the coumarin lactone ring  Michael reaction
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