Intramolecular reactions of N-nitrenes with alkenes

Abstract

Oxidation of 2-but-1-enyl- and 2-(1-phenylbut-1-enyl)-3-aminoquinazplin-4(3H)-ones (8) and (10), respectively, generates the corresponding N-nitrenes which are trapped intramolecularly by the double bonds. The results from competitive intramolecular trapping of the N-nitrene by different double bonds in 3-aminoquinazolones bearing bifurcated chains in position 2 [e.g.(25), (26), (27), and (28)] indicate that these intramolecular nitrene additions are non-concerted and, as in the corresponding intramolecular addition to aromatic rings, proceed via 7-membered transition states with the nitrene functioning as an electrophile.