Aziridination of alkenes using 3-acetoxyaminoquinazolin-4-(3 H) ones in the presence of tertiary amines: evidence for an azaimide (N-nitrene) intermediate

RS Atkinson, E Barker

Index: Atkinson, Robert S.; Barker, Emma Journal of the Chemical Society, Chemical Communications, 1995 , # 8 p. 819 - 820

Full Text: HTML

Citation Number: 14

Abstract

Oxidation of certain heterocyclic N-amino compounds with lead tetraacetate (LTA) in the presence of alkenes gives aziridinesl (Scheme 1). ... 1 Scheme 1 The reactive intermediates in these aziridinations were thought to be N-nitrenes (azaimides) 1 but, at least for 2-substituted-3-aminoquinazolinones 2 (Scheme 2) are now known to be 3-acetoxyaminoquinazolinones 3.2 As a result, aziridination using 3 can be considered as the nitrogen analogue of epoxidation using peroxyacetic ...