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Synthesis of 1,2-azidoamines


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An efficient ring opening of epoxides and aziridines has been carried out at room temperature using poly(ethylene glycol) (PEG-400) as reaction medium to form the corresponding 2-azido alcohols and 2-azido amines, respectively, in excellent yields within 30-45 minutes and with high regio- and stereoselectivity.
B. Das, V. S. Reddy, F. Tehseen, M. Krishnaiah, Synthesis, 2007, 666-668.

Tetrabutylammonium fluoride promotes ring-opening reactions of aziridines with trimethylsilyl compounds to give the corresponding products regioselectively in excellent yield. This reaction provides a facile and efficient access to cyano-, azido-, or chloroamines. The products are easily transformed to vicinal diamines or β-amino acids.
J. Wu, X.-L. Hou, L.-X. Dai, J. Org. Chem., 2000, 65, 1344-1348.

A wide variety of epoxides and aziridines were converted to the corresponding β-azido alcohols and β-azido amines with sodium azide using OxoneŽ in aqueous acetonitrile. The reactions were highly regioselective and efficient with excellent yields at room temperature under mild reaction conditions.
G. Sabitha, S. R. Babu, M. S. K. Reddy, J. S. Yadav, Synthesis, 2002, 2254-2258.

Aziridines react smoothly with sodium azide and sodium cyanide in the presence of a catalytic amount of lithium perchlorate under essentially mild and neutral reaction conditions to afford the corresponding β-azido and β-cyanoamines in high yields with high regioselectivity.
J. S. Yadav, B. V. S. Reddy, G. Parimala, P. Venkatram Reddy, Synthesis, 2002, 2383-2386.

A convenient, efficient, and highly regioselective synthesis of 1,2-azidoalcohols and 1,2-azidoamines in excellent yields has been achieved by using cerium(III) chloride and sodium azide for a mild ring opening of epoxides and aziridines.
G. Sabitha, R. S. Babu, M. Rajkumar, J. S. Vadav, Org. Lett., 2002, 4, 343-345.

β-Functionalized sulfonamides were produced in good yields by the regioselective ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N',N'-tetramethylethylenediamine (TMEDA).
S. Minakata, Y. Okada, Y. Oderaotoshi, M. Komatsu, Org. Lett., 2005, 7, 3509-3512.