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Paper | Regular issue | Vol 26, No. 3, 1987, pp.731-744
Published online, 1st January, 1970
DOI: 10.3987/R-1987-03-0731
Homolytic Alkoxycarbonylation Reactions in Two-phase Systems 3. Introduction of a Single Carboxylic Acid Ester Function into Cyano- or Alkoxycarbonyl Substituted N-Heteroaromatics

Gottfried Heinisch and Gerhard Lötsch

*Institut für Pharmazeutische Chemie, Universität Wien , Pharmaziezentrum, Althanstrasse, 14 A-1090 Wien, Austria


Homolytic alkoxycarbonylatlon reactions with cyanopyridines 1a, 2a, 3a, alkyl pyridinecarboxylates 1b, 2b, 3b, 3c and ethyl 4-pyridazinecarboxylate 4 in presence of dichloromethane were studied. It is demonstrated that under these conditions multiple substitution in general is suppressed markedly. Thus, this experimentally simple procedure represents an efficient and versatile method for single-step preparations of slkyl cyanopyridinecarboxylates 7a, 8a, 9a, 10a. Furthermore,it provides convenient access to so far not available mixed esters 5b, 7b, 8b,10b,13, derived from 2,3-pyridine-, 2,4-pyridine-, 3,4- pyridine- and 4,5-pyridazinedicarbaxylic acid.