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Paper | Regular issue | Vol 57, No. 11, 2002, pp.2115-2128
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9599
Study of the Reactivity of 5-Alkynyl-4-chloro- and 4-Alkynyl-5-chloropyridazin-3(2H)-ones towards Oxygen and Sulfur Nucleophiles

Omar R’kyek, Bert U. W. Maes, Guy L. F. Lemière,* and Roger A. Dommisse

*Department of Chemistry, University of Antwerp (RUCA), Groenenborgerlaan 171, B-2020 Antwerp, Belgium

Abstract

A study of the reactivity of 5-alkynyl-4-chloro- (1a,b) and 4-alkynyl-5-chloropyridazin-3(2H)-ones (4a,b) towards oxygen and sulfur nucleophiles (NaOCH3, NaSCH3, KOH and Na2S) is reported. The synthesis of 5-alkynyl-2-methyl-4-methoxy- (2a,b) and 5-alkynyl-2-methyl-4-methylthiopyridazin-3(2H)-ones (3a,b) and their regioisomers 4-alkynyl-2-methyl-5-methoxy- (5a,b) and 4-alkynyl-2-methyl-5-methylthiopyridazin-3(2H)-ones (6a,b) is described, as well as the synthesis of 2-substituted 6-methylfuro[2,3-d]- (7a,b,c) and 2-substituted 6-methylthieno[2,3-d]pyridazin-7(6H)-ones (8a,b) and their regioisomers 2-substituted 5-methylfuro[2,3-d]- (9a,b,c) and 2-substituted 5-methylthieno[2,3-d]pyridazin-4(5H)-ones (10a,b).