A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes

[Image: see text] Indoles are converted into α-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolyl aldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 °C under microwave irradiation undergo loss of the...

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Autores principales: Markey, Sophie J., Lewis, William, Moody, Christopher J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2013
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3971735/
https://www.ncbi.nlm.nih.gov/pubmed/24280001
http://dx.doi.org/10.1021/ol403191k
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author Markey, Sophie J.
Lewis, William
Moody, Christopher J.
author_facet Markey, Sophie J.
Lewis, William
Moody, Christopher J.
author_sort Markey, Sophie J.
collection PubMed
description [Image: see text] Indoles are converted into α-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolyl aldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 °C under microwave irradiation undergo loss of the Boc-group, and 6π-electrocyclization to α-carbolines, following aromatization by loss of methanol (11 examples, 30–90% yield).
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spelling pubmed-39717352014-04-01 A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes Markey, Sophie J. Lewis, William Moody, Christopher J. Org Lett [Image: see text] Indoles are converted into α-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolyl aldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 °C under microwave irradiation undergo loss of the Boc-group, and 6π-electrocyclization to α-carbolines, following aromatization by loss of methanol (11 examples, 30–90% yield). American Chemical Society 2013-11-26 2013-12-20 /pmc/articles/PMC3971735/ /pubmed/24280001 http://dx.doi.org/10.1021/ol403191k Text en Copyright © 2013 American Chemical Society Terms of Use CC-BY (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html)
spellingShingle Markey, Sophie J.
Lewis, William
Moody, Christopher J.
A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes
title A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes
title_full A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes
title_fullStr A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes
title_full_unstemmed A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes
title_short A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes
title_sort new route to α-carbolines based on 6π-electrocyclization of indole-3-alkenyl oximes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3971735/
https://www.ncbi.nlm.nih.gov/pubmed/24280001
http://dx.doi.org/10.1021/ol403191k
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