A novel method for the synthesis of 2-haloalkyl-3(2H)-pyridazinones by o → N-alkyl rearrangement

P. Mátyus, Nándor Makk, Endre Kasztreiner, Gyula Jerkovich

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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.

Original languageEnglish
Pages (from-to)67-77
Number of pages11
JournalHeterocycles
Volume29
Issue number1
Publication statusPublished - Jan 1 1989

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Dilatation and Curettage
thionyl chloride

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  • Organic Chemistry

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A novel method for the synthesis of 2-haloalkyl-3(2H)-pyridazinones by o → N-alkyl rearrangement. / Mátyus, P.; Makk, Nándor; Kasztreiner, Endre; Jerkovich, Gyula.

In: Heterocycles, Vol. 29, No. 1, 01.01.1989, p. 67-77.

Research output: Contribution to journalArticle

Mátyus, P. ; Makk, Nándor ; Kasztreiner, Endre ; Jerkovich, Gyula. / A novel method for the synthesis of 2-haloalkyl-3(2H)-pyridazinones by o → N-alkyl rearrangement. In: Heterocycles. 1989 ; Vol. 29, No. 1. pp. 67-77.
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