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Paper | Regular issue | Vol 29, No. 1, 1989, pp.67-77
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4622
A Novel Mehtod for the Synthesis of 2-Haloalkyl-3(2H)-pyridazinones by ON-Alkyl Rearrangement

Péter Mátyus,* Nándor Makk, Endre Kasztreiner, and Gyula Jerkovich

*Institute for Drug Research Ltd., H-1325 Budapest, POB 82, Hungary

Abstract

The reaction of (6-substituted 3-pyridazinyloxy)alkanols 2a-d, 3a-d and 14a-c with thionyl chloride is described. The 2-chloroalkylpyridazinones 5b-d, 6b-d and 15a-c were formed from 2b-d, 3b-d and 14a-c, respectively, while the 3-chloroalkoxypyridazines, 7a and 8a were isolated from the reaction of 2a and 3a, respectively. It was shown by chemical and spectroscopic evidences that the rearrangement reaction followed an intramolecular process through bicyclic intermediates.