Aziridination of alkenes using 3-acetoxyamino-2-trifluoromethylquinazolin-4(3H)-one

Abstract

Oxidation of 3-amino-2-trifluoromethylquinazolin-4(3H)-one 6 with lead tetraacetate in dichloromethane gives the title 3-acetoxyamino derivative 7 which is isolable at room temperature and considerably more stable than the corresponding 2-alkyl substituted analogues. Compound 7 aziridinates alkenes in yields which are consistently higher than those from the 2-alkyl substituted analogues. Aziridinations using 3-acetoxyaminoquinazolinones bearing other electron-withdrawing groups on the 2-position of the quinazolinone ring have been examined.