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 |
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Authors: | M. P. Nemeryuk V. D. Dimitrova O. S. Anisimova A. L. Sedov N. P. Solov'eva V. F. Traven |
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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 |
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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. |
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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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