(1α and 1β)Methyl-1,1a,2,3,4,5-hexahydro-11H-azirino-[1′2′:2,3][1,2]diazocino[8,1-b]quinazolin-11-one: preference for a trans-fused aziridine in an eight-membered ring

Abstract

Intramolecular trapping of the nitrenes from oxidation of cis- and trans-2-(hept-2-en-7-yl)-3-amino-quinazolinones (1) and (3) gives the aziridines (2) and (4) respectively; in solution at room temperature (4) contains a mixture of nitrogen invertomers with the major invertomer having a trans-aziridine ring fusion, the latter being the only form present in the crystalline state.