Journal of the Chemical Society. Perkin transactions I p. 1205 - 1211 (1996)
Update date:2022-07-30
Topics:
Griffin, Roger J.
Evers, Elaine
Davison, Richard
Gibson, Ashleigh E.
Layton, Deborah
Irwin, William J.
A series of 4-azidobenzylcarbamates [4-N3-C6H4-CH2-O-CO-N(H)-C 6H4-X; X = H, Me, MeO, Br, Cl, NO2] have been prepared in good yield, and in high purity, by reaction of 4-azidobenzyl alcohol with the corresponding aryl isocyanate, or by displacement of 4-nitrophenol from 4-azidobenzyl-4-nitrophenylcarbonate by the appropriate amine. The 4-azidobenzylcarbamates were shown to undergo rapid reduction in the presence of dithiothreitol, and the resultant 4-aminobenzylcarbamates underwent immediate cascade degradation to release the target amine. The mild conditions used in this conversion may prove useful in the protection of amines during synthetic procedures or as a possible mode of bioactivation of prodrugs.
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