Aziridination of alkenes using 3-amino-2-ethylquinazolin-4(3H)-one and lead tetra-acetate–trifluoroacetic acid

Abstract

Efficient aziridination of terminal alkenes by oxidative addition [lead tetra-acetate (LTA)] of the N-aminoquinazoline (1) is effected by inclusion of trifluoroacetic acid (TFA) in the mixture. The effect of (a) substitution of either lead tetratrifluoroacetate or [bis(trifluoroacetoxy) iodo]benzene for LTA or (b) addition of preformed N-acetoxyaminoquinazolone (7) to allyl chloride in the presence of TFA, suggests that the major factor in bringing about improved aziridination yields of allyl chloride and other unreactive alkenes is protonation of the quinazolone ring.