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Paper | Regular issue | Vol 32, No. 10, 1991, pp.1913-1921
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5799
Reactions of 3,5-Dimethyl-4-nitroisoxazole with Cyclic Enamines and 1-Diethylaminopropyne

Rodolfo Nesi,* Donatella Giomi,* Sandro Papaleo, Stefania Turchi, Paolo Dapporto, and Paola Paoli

*CNR, Centro di Studio Sulla Chimica e la Struttura dei Composti Eterociclici e lolo Applicazioni, c/o Dipartimento di Chimica Organica "Ugo Schiff", Università di Firenze, Via Gino Capponi 9, I-50121 Firenze, Italy

Abstract

3,5-Dimethyl-4-nitroisoxazole (1) was found to undergo tandem condensation-cyclization processes with 4-(1-cyclopenten-1-yl)- and 4-(1-cyclohexen-1-yl)morpholine in ethanol solution to give, through the intermediates (4) and (7), the N-oxides (5) and (9), respectively. The reactivity of 1 towards 1-diethylaminopropyne in different solvents was also investigated; the structure of the unexpected acyloxime (13), coming from the above reagents in acetonitrile, was determined by an X-ray analysis. Plausible mechanistic pathways for these new reactions are suggested.