Aziridines and Azirines: Fused-ring Derivatives

This review covers the literature on fused-ring aziridines and azirines from late 1995 through 2006. The review considers the two general types of fused-ring aziridines. The two structural classes of fused-ring aziridines are: (1) fused-ring aziridines with the aziridine nitrogen at the bridgehead position and fused-ring aziridines with the aziridine nitrogen exocyclic to the annulated ring. Several aspects of the structure and reactivity of fused-ring aziridine and azirines are covered. Methods for the formation, and reactions of fused-ring aziridines have been considered separately. The formation and transformations of fused-ring aziridinium ions and highly unstable yet useful fused-ring azirines are also covered. In addition to the synthesis and reactivity of the basic fused-ring aziridines, the synthesis of fused-ring aziridine containing natural products such as azinomycin, mitomycin, and FR900482 are discussed. The use of fused-ring aziridines and aziridinium ions for the syntheses of a number of natural products are also presented.