Isoxazoles and Isoxazolines by 1, 3??Dipolar Cycloaddition: Base??Catalysed Condensation of Primary Nitro Compounds with Dipolarophiles

F Machetti, L Cecchi, E Trogu…

Index: Machetti, Fabrizio; Cecchi, Luca; Trogu, Elena; De Sarlo, Francesco European Journal of Organic Chemistry, 2007 , # 26 p. 4352 - 4359

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Citation Number: 25

Abstract

Abstract 1, 4-Diazabicyclo [2.2. 2] octane (DABCO) or other suitable N-bases cause primary activated nitro compounds to condense with alkenes to yield isoxazolines or with alkynes to give isoxazoles. As the molar ratio of the base with respect to the dipolarophile decreased, the reaction became slower, but the nitro compound became more resistant to hydrolytic cleavage. The best results were achieved with a molar ratio of base in the range of 0.05– ...