Acid-catalyzed rearrangement of some steroidal isoxazolidines
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1999
Authors
Rajković, Milica M.Lorenc, Ljubinka B.
Juranić, Ivan

Vitnik, Željko

Mihailović, Milhailo Lj.
Article (Published version)

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Acid-catalyzed reaction of the steroidal Δ 1 -unsaturated 3β,5β- epoxyimino compound 2 and Δ 3 -unsaturated 1β,5β-epoxyimino products 3 and 7, results in intramolecular rearrangement involving the N-CH 3 group to give the corresponding perhydro-3,1-oxazine derivatives 9-11. Under similar reaction conditions, the saturated analogues 4, 6 and 8 remain unchanged. The difference in reactivity between the unsaturated and saturated compounds is studied and elucidated by the semiempirical molecular orbital MNDO-PM3 method.
Keywords:
steroidal / rearrangement / Acid-catalyzed reaction / semiempirical molecular orbital MNDO-PM3 method / Isoxazolidines / Molecular rearrangement / Perhydro-oxazines / Seco steroidsSource:
Tetrahedron, 1999, 55, 21, 6681-6690Publisher:
- Elsevier
Funding / projects:
- The Serbian Academy of Science and Arts
- The Serbian Ministry of Sciences and Technology
DOI: 10.1016/S0040-4020(99)00314-2
ISSN: 0040-4020; 1464-5416
Scopus: 2-s2.0-0033591170
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IHTMTY - JOUR AU - Rajković, Milica M. AU - Lorenc, Ljubinka B. AU - Juranić, Ivan AU - Vitnik, Željko AU - Mihailović, Milhailo Lj. PY - 1999 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4391 AB - Acid-catalyzed reaction of the steroidal Δ 1 -unsaturated 3β,5β- epoxyimino compound 2 and Δ 3 -unsaturated 1β,5β-epoxyimino products 3 and 7, results in intramolecular rearrangement involving the N-CH 3 group to give the corresponding perhydro-3,1-oxazine derivatives 9-11. Under similar reaction conditions, the saturated analogues 4, 6 and 8 remain unchanged. The difference in reactivity between the unsaturated and saturated compounds is studied and elucidated by the semiempirical molecular orbital MNDO-PM3 method. PB - Elsevier T2 - Tetrahedron T1 - Acid-catalyzed rearrangement of some steroidal isoxazolidines VL - 55 IS - 21 SP - 6681 EP - 6690 DO - 10.1016/S0040-4020(99)00314-2 ER -
@article{ author = "Rajković, Milica M. and Lorenc, Ljubinka B. and Juranić, Ivan and Vitnik, Željko and Mihailović, Milhailo Lj.", year = "1999", abstract = "Acid-catalyzed reaction of the steroidal Δ 1 -unsaturated 3β,5β- epoxyimino compound 2 and Δ 3 -unsaturated 1β,5β-epoxyimino products 3 and 7, results in intramolecular rearrangement involving the N-CH 3 group to give the corresponding perhydro-3,1-oxazine derivatives 9-11. Under similar reaction conditions, the saturated analogues 4, 6 and 8 remain unchanged. The difference in reactivity between the unsaturated and saturated compounds is studied and elucidated by the semiempirical molecular orbital MNDO-PM3 method.", publisher = "Elsevier", journal = "Tetrahedron", title = "Acid-catalyzed rearrangement of some steroidal isoxazolidines", volume = "55", number = "21", pages = "6681-6690", doi = "10.1016/S0040-4020(99)00314-2" }
Rajković, M. M., Lorenc, L. B., Juranić, I., Vitnik, Ž.,& Mihailović, M. Lj.. (1999). Acid-catalyzed rearrangement of some steroidal isoxazolidines. in Tetrahedron Elsevier., 55(21), 6681-6690. https://doi.org/10.1016/S0040-4020(99)00314-2
Rajković MM, Lorenc LB, Juranić I, Vitnik Ž, Mihailović ML. Acid-catalyzed rearrangement of some steroidal isoxazolidines. in Tetrahedron. 1999;55(21):6681-6690. doi:10.1016/S0040-4020(99)00314-2 .
Rajković, Milica M., Lorenc, Ljubinka B., Juranić, Ivan, Vitnik, Željko, Mihailović, Milhailo Lj., "Acid-catalyzed rearrangement of some steroidal isoxazolidines" in Tetrahedron, 55, no. 21 (1999):6681-6690, https://doi.org/10.1016/S0040-4020(99)00314-2 . .