Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration

[Image: see text] Herein, we disclose the first report on iodo-cycloisomerization of 1-(indol-3-yl)-1-arylbut-3-yn-2-ols to form 3-iodocarbazoles. The synthesis proceeds through a cascade 5-endo-spirocyclization, followed by selective 1,2-alkyl migration. This method governs the green synthesis prin...

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Autores principales: Yaragorla, Srinivasarao, Bag, Debojyoti, Dada, Ravikrishna, Jose, K.V. Jovan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6643784/
https://www.ncbi.nlm.nih.gov/pubmed/31458169
http://dx.doi.org/10.1021/acsomega.8b02393
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author Yaragorla, Srinivasarao
Bag, Debojyoti
Dada, Ravikrishna
Jose, K.V. Jovan
author_facet Yaragorla, Srinivasarao
Bag, Debojyoti
Dada, Ravikrishna
Jose, K.V. Jovan
author_sort Yaragorla, Srinivasarao
collection PubMed
description [Image: see text] Herein, we disclose the first report on iodo-cycloisomerization of 1-(indol-3-yl)-1-arylbut-3-yn-2-ols to form 3-iodocarbazoles. The synthesis proceeds through a cascade 5-endo-spirocyclization, followed by selective 1,2-alkyl migration. This method governs the green synthesis principles such as open-flask reaction, AcOEt as the solvent, rt reaction with short time, use of iodine, and broad substrate scope with atom and step economy.
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spelling pubmed-66437842019-08-27 Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration Yaragorla, Srinivasarao Bag, Debojyoti Dada, Ravikrishna Jose, K.V. Jovan ACS Omega [Image: see text] Herein, we disclose the first report on iodo-cycloisomerization of 1-(indol-3-yl)-1-arylbut-3-yn-2-ols to form 3-iodocarbazoles. The synthesis proceeds through a cascade 5-endo-spirocyclization, followed by selective 1,2-alkyl migration. This method governs the green synthesis principles such as open-flask reaction, AcOEt as the solvent, rt reaction with short time, use of iodine, and broad substrate scope with atom and step economy. American Chemical Society 2018-11-07 /pmc/articles/PMC6643784/ /pubmed/31458169 http://dx.doi.org/10.1021/acsomega.8b02393 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Yaragorla, Srinivasarao
Bag, Debojyoti
Dada, Ravikrishna
Jose, K.V. Jovan
Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration
title Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration
title_full Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration
title_fullStr Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration
title_full_unstemmed Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration
title_short Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration
title_sort iodo-cycloisomerization of aryl(indol-3-yl)methane-tethered propargyl alcohols to 3-iodocarbazoles via selective 1,2-alkyl migration
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6643784/
https://www.ncbi.nlm.nih.gov/pubmed/31458169
http://dx.doi.org/10.1021/acsomega.8b02393
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