Facile synthesis of disubstituted isoxazoles from homopropargylic alcohol via C═N bond formation.

ABSTRACT

A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H2O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C═N bond and C═O bond, C-H oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.