Aziridination of alkenes with 3-acetoxyaminoquinazolinones in the presence of hexamethyldisilazane

Abstract

Yields of aziridines from reaction of some alkenes, including α,β-unsaturated esters, with 3-acetoxyamino-2-isopropylquinazolinone 6 (Q³NHOAc) are greatly increased in the presence of hexamethyldisilazane (HMDS). A mono-aziridination product of naphthalene is obtained only in the presence of HMDS. It is concluded that the enhanced yields in these aziridinations are the result of scavenging of acetic acid by HMDS, thus prolonging the lifetime of the aziridinating agent Q³NHOAc.

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