CER - Central Repository
Institute of Chemistry, Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrillic)
    • Serbian (Latin)
  • Login
View Item 
  •   CER
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
  •   CER
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Acid-catalyzed rearrangement of some steroidal isoxazolidines

Authorized Users Only
1999
Authors
Rajković, Milica M.
Lorenc, Ljubinka B.
Juranić, Ivan
Vitnik, Željko
Mihailović, Milhailo Lj.
Article (Published version)
Metadata
Show full item record
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.
Keywords:
steroidal / rearrangement / Acid-catalyzed reaction / semiempirical molecular orbital MNDO-PM3 method / Isoxazolidines / Molecular rearrangement / Perhydro-oxazines / Seco steroids
Source:
Tetrahedron, 1999, 55, 21, 6681-6690
Publisher:
  • 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
[ Google Scholar ]
6
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4391
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - 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 . .

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

re3dataOpenAIRERCUB
 

 

All of DSpaceInstitutions/communitiesAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

re3dataOpenAIRERCUB