Categories: C-N Bond Formation > Synthesis of azides >
Synthesis of 1,2-azidoamines
Related |
|
Recent Literature
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.