Faculty of Chemistry Repository - Cherry
University of Belgrade - Faculty of Chemistry
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrilic)
    • Serbian (Latin)
  • Login
View Item 
  •   Faculty of Chemistry Repository - Cherry
  • Hemijski fakultet
  • Publikacije
  • View Item
  •   Faculty of Chemistry Repository - Cherry
  • Hemijski fakultet
  • Publikacije
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B

Authorized Users Only
2013
Authors
Tasić, Gordana
Simić, Milena R.
Popovic, Stanimir
Husinec, Suren
Maslak, Veselin
Savić, Vladimir
Article (Published version)
Metadata
Show full item record
Abstract
Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B.
Keywords:
N-Vinylindoles / Isomerisation / Base / Debromoarborescidine B
Source:
Tetrahedron Letters, 2013, 54, 34, 4536-4539
Publisher:
  • Pergamon-Elsevier Science Ltd, Oxford
Projects:
  • Computational design, synthesis and biological evaluation of new heterocyclic compounds as selective tumorogenesis inhibitors (RS-172009)
Note:
  • Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3501

DOI: 10.1016/j.tetlet.2013.06.069

ISSN: 0040-4039

WoS: 000322608000011

Scopus: 2-s2.0-84880293280
[ Google Scholar ]
7
6
URI
http://cherry.chem.bg.ac.rs/handle/123456789/1382
Collections
  • Publikacije
Institution
Hemijski fakultet
TY  - JOUR
AU  - Tasić, Gordana
AU  - Simić, Milena R.
AU  - Popovic, Stanimir
AU  - Husinec, Suren
AU  - Maslak, Veselin
AU  - Savić, Vladimir
PY  - 2013
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1382
AB  - Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron Letters
T1  - Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B
VL  - 54
IS  - 34
SP  - 4536
EP  - 4539
DO  - 10.1016/j.tetlet.2013.06.069
ER  - 
@article{
author = "Tasić, Gordana and Simić, Milena R. and Popovic, Stanimir and Husinec, Suren and Maslak, Veselin and Savić, Vladimir",
year = "2013",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1382",
abstract = "Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron Letters",
title = "Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B",
volume = "54",
number = "34",
pages = "4536-4539",
doi = "10.1016/j.tetlet.2013.06.069"
}
Tasić G, Simić MR, Popovic S, Husinec S, Maslak V, Savić V. Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B. Tetrahedron Letters. 2013;54(34):4536-4539
Tasić, G., Simić, M. R., Popovic, S., Husinec, S., Maslak, V.,& Savić, V. (2013). Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B.
Tetrahedron LettersPergamon-Elsevier Science Ltd, Oxford., 54(34), 4536-4539.
https://doi.org/10.1016/j.tetlet.2013.06.069
Tasić Gordana, Simić Milena R., Popovic Stanimir, Husinec Suren, Maslak Veselin, Savić Vladimir, "Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B" 54, no. 34 (2013):4536-4539,
https://doi.org/10.1016/j.tetlet.2013.06.069 .

DSpace software copyright © 2002-2015  DuraSpace
About CHERRY - CHEmistry RepositoRY | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceInstitutionsAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CHERRY - CHEmistry RepositoRY | Send Feedback

OpenAIRERCUB