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
TY - JOUR
AU - Tasić, Gordana
AU - Simić, Milena R.
AU - Popović, Stanimir
AU - Husinec, Suren
AU - Maslak, Veselin
AU - Savić, Vladimir
PY - 2013
UR - http://farfar.pharmacy.bg.ac.rs/handle/123456789/1973
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3503
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 - Oxford : Pergamon-Elsevier Science Ltd
T2 - Tetrahedron-Asymmetry
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 Popović, Stanimir and Husinec, Suren and Maslak, Veselin and Savić, Vladimir",
year = "2013",
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 = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron-Asymmetry",
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, M. R., Popović, S., Husinec, S., Maslak, V.,& Savić, V.. (2013). Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B. in Tetrahedron-Asymmetry
Oxford : Pergamon-Elsevier Science Ltd., 54(34), 4536-4539.
https://doi.org/10.1016/j.tetlet.2013.06.069
Tasić G, Simić MR, Popović S, Husinec S, Maslak V, Savić V. Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B. in Tetrahedron-Asymmetry. 2013;54(34):4536-4539.
doi:10.1016/j.tetlet.2013.06.069 .
Tasić, Gordana, Simić, Milena R., Popović, Stanimir, Husinec, Suren, Maslak, Veselin, Savić, Vladimir, "Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B" in Tetrahedron-Asymmetry, 54, no. 34 (2013):4536-4539,
https://doi.org/10.1016/j.tetlet.2013.06.069 . .
