Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B
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2013
Authors
Tasić, GordanaSimić, Milena R.

Popović, Stanimir
Husinec, Suren
Maslak, Veselin

Savić, Vladimir

Article (Published version)

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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 BSource:
Tetrahedron-Asymmetry, 2013, 54, 34, 4536-4539Publisher:
- Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
DOI: 10.1016/j.tetlet.2013.06.069
ISSN: 0040-4039
WoS: 000322608000011
Scopus: 2-s2.0-84880293280
URI
http://farfar.pharmacy.bg.ac.rs/handle/123456789/1973https://cer.ihtm.bg.ac.rs/handle/123456789/3503
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IHTMTY - 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 . .