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Paper | Regular issue | Vol 32, No. 6, 1991, pp.1173-1179
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5727
Reductive Cleavage of Isoxazolo[3,4-d]pyridazinones: A Synthetic Approach to Various 4,5-Functionalized 3(2H)-Pyridazinones

Vittorio Dal Piaz,* Giovanna Ciciani, and Maria Paola Giovannoni

*Dipartimento di Scienze Farmaceutiche, Università di Firenze, Via Gino Capponi 9, I-50121 Firenze, Italy

Abstract

4-Aminopyridazin-3(2H)-ones substituted at position 5 with a variety of oxygenated carbon chains were obtained in good yields by reductive opening of the pentatomic ring of isoxazolo[3,4-d]pyridazinones (1). Starting from ethyl 4-acylisoxazole-3-carboxylates, several 4,5-functionalized 3(2H)-pyridazinones (3) are obtained in a one step by treatment with the appropriate hydrazine and Pd/C.