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

  • М. П. Немерюк D. I. Mendeleev Russian University of Chemical Technology, Moscow 125047
  • В. Д. Димитрова D. I. Mendeleev Russian University of Chemical Technology, Moscow 125047
  • О. С. Анисимова Center for Drug Chemistry, All Russian Research Institute of Pharmaceutical Chemistry, Moscow 119815
  • А. Л. Седов Center for Drug Chemistry, All Russian Research Institute of Pharmaceutical Chemistry, Moscow 119815
  • Н. П. Соловьева Center for Drug Chemistry, All Russian Research Institute of Pharmaceutical Chemistry, Moscow 119815
  • В. Ф. Травень D. I. Mendeleev Russian University of Chemical Technology, Moscow 125047

DOI:

https://doi.org/10.1007/8164

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

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.

How to Cite
Nemeryuk, M. P.; Dimitrova, V. D.; Anisimova, O. S.; Sedov, A. L.; Solov'eva, N. P.; Traven, V. F.  Chem. Heterocycl. Compd. 2005, 41, 1255. [Khim. Geterotsikl. Soedin. 2005, 1502.]

For this article in the English edition, see DOI 10.1007/s10593-005-0311-4

 

Downloads

Published

2023-10-18

Issue

No. 10 (2005)

Section

Original Papers