ChemInform Abstract: Electrochemical Reduction of Isoxazoles and Related Compounds.

ChemInform Abstract

Some isoxazoles (I), isoxazolines (IV) and their quaternized derivatives (II), (III) are investigated by polarography and preparative reduction. A reductive cleavage of the oxygen-nitrogen bond without reduction of the carbon-nitrogen bond can be achieved in protic medium for the quaternized derivatives (II), (III), whereas for the parent compounds (I), (IV) this is possible only in aprotic medium. The individual preparative reactions described are shown in the scheme. Thus, in this manner, isoxazoles and isoxazolines may be transformed preferentially via quaternization to β-diketones such as (VII) (formed from the reduction products (V)), β-hydroxyketones such as (X), or, using suitable reaction conditions, to 1,3-aminoalcohols such as (VI) or (XI).