Treatment of steroidal isoxazolidines 3a, 3b and 5b with N-methylhydroxylamine hydrochloride in boiling ethanol-pyridine (1:1) solution results in elimination of the CH3NH2fragment, affording products of oxidative hydrolysis 4a, 4b, and 6b, while acid-catalyzed reaction of isoxazolidines 2a, 3a and 5b leads to rearrangement involving the N-CH3 group with formation of the perhydro-3,1-oxazine derivatives 8a, 9a and 10b.
TY - JOUR
AU - Rajković, Milica M.
AU - Lorenc, Ljubinka
AU - Petrović, Ivanka
AU - Milovanović, Aleksandar Ž.
AU - Mihailović, Milhailo Lj.
PY - 1991
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4362
AB - Treatment of steroidal isoxazolidines 3a, 3b and 5b with N-methylhydroxylamine hydrochloride in boiling ethanol-pyridine (1:1) solution results in elimination of the CH3NH2fragment, affording products of oxidative hydrolysis 4a, 4b, and 6b, while acid-catalyzed reaction of isoxazolidines 2a, 3a and 5b leads to rearrangement involving the N-CH3 group with formation of the perhydro-3,1-oxazine derivatives 8a, 9a and 10b.
PB - Elsevier
T2 - Tetrahedron Letters
T1 - Oxidative hydrolysis and acid-catalyzed rearrangement of steroidal isoxazolidines
VL - 32
IS - 51
SP - 7605
EP - 7608
DO - 10.1016/0040-4039(91)80546-I
ER -
@article{
author = "Rajković, Milica M. and Lorenc, Ljubinka and Petrović, Ivanka and Milovanović, Aleksandar Ž. and Mihailović, Milhailo Lj.",
year = "1991",
abstract = "Treatment of steroidal isoxazolidines 3a, 3b and 5b with N-methylhydroxylamine hydrochloride in boiling ethanol-pyridine (1:1) solution results in elimination of the CH3NH2fragment, affording products of oxidative hydrolysis 4a, 4b, and 6b, while acid-catalyzed reaction of isoxazolidines 2a, 3a and 5b leads to rearrangement involving the N-CH3 group with formation of the perhydro-3,1-oxazine derivatives 8a, 9a and 10b.",
publisher = "Elsevier",
journal = "Tetrahedron Letters",
title = "Oxidative hydrolysis and acid-catalyzed rearrangement of steroidal isoxazolidines",
volume = "32",
number = "51",
pages = "7605-7608",
doi = "10.1016/0040-4039(91)80546-I"
}
Rajković, M. M., Lorenc, L., Petrović, I., Milovanović, A. Ž.,& Mihailović, M. Lj.. (1991). Oxidative hydrolysis and acid-catalyzed rearrangement of steroidal isoxazolidines. in Tetrahedron Letters
Elsevier., 32(51), 7605-7608.
https://doi.org/10.1016/0040-4039(91)80546-I
Rajković MM, Lorenc L, Petrović I, Milovanović AŽ, Mihailović ML. Oxidative hydrolysis and acid-catalyzed rearrangement of steroidal isoxazolidines. in Tetrahedron Letters. 1991;32(51):7605-7608.
doi:10.1016/0040-4039(91)80546-I .
Rajković, Milica M., Lorenc, Ljubinka, Petrović, Ivanka, Milovanović, Aleksandar Ž., Mihailović, Milhailo Lj., "Oxidative hydrolysis and acid-catalyzed rearrangement of steroidal isoxazolidines" in Tetrahedron Letters, 32, no. 51 (1991):7605-7608,
https://doi.org/10.1016/0040-4039(91)80546-I . .
