Journal of Organic Chemistry p. 4648 - 4653 (1991)
Update date:2022-07-29
Topics:
Han, Insook
Kohn, Harold
7-Aminoleucoaziridinomitosene (2a) has been proposed as a key intermediate in the reductive activation process for the antineoplastic agent, mitomycin C (1a).Little is known about 2a and its oxidised equivalent, 7-aminoaziridinomitosene (3a).An expedient electrochemical procedure for 3a and the corresponding N-methyl analogue 3b has been developed.NMR spectral studies of 3a in DMF-d7 and DMSO-d6 provided important information concerning the solution-state structure for this adduct.Factors controlling the aziridine ring-opening process under reductive and nonreductive conditions have been determined, as well as evidence for the intermediacy of 2a in the reductive activation cascade of 1a.
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