A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide

A straightforward synthesis of 4,4-spirocyclic indol γ-lactams by tandem radical cyclization of iodoaryl allyl azides with CO was achieved. The reaction of iodoaryl allyl azides, TTMSS and AIBN under CO pressure (80 atm) in THF at 80 °C gave the desired 4,4-spirocyclic indoline, benzofuran, and oxin...

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Autores principales: Ueda, Mitsuhiro, Uenoyama, Yoshitaka, Terasoma, Nozomi, Doi, Shoko, Kobayashi, Shoji, Ryu, Ilhyong, Murphy, John A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740707/
https://www.ncbi.nlm.nih.gov/pubmed/23946829
http://dx.doi.org/10.3762/bjoc.9.151
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author Ueda, Mitsuhiro
Uenoyama, Yoshitaka
Terasoma, Nozomi
Doi, Shoko
Kobayashi, Shoji
Ryu, Ilhyong
Murphy, John A
author_facet Ueda, Mitsuhiro
Uenoyama, Yoshitaka
Terasoma, Nozomi
Doi, Shoko
Kobayashi, Shoji
Ryu, Ilhyong
Murphy, John A
author_sort Ueda, Mitsuhiro
collection PubMed
description A straightforward synthesis of 4,4-spirocyclic indol γ-lactams by tandem radical cyclization of iodoaryl allyl azides with CO was achieved. The reaction of iodoaryl allyl azides, TTMSS and AIBN under CO pressure (80 atm) in THF at 80 °C gave the desired 4,4-spirocyclic indoline, benzofuran, and oxindole γ-lactams in moderate to good yields.
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spelling pubmed-37407072013-08-14 A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide Ueda, Mitsuhiro Uenoyama, Yoshitaka Terasoma, Nozomi Doi, Shoko Kobayashi, Shoji Ryu, Ilhyong Murphy, John A Beilstein J Org Chem Letter A straightforward synthesis of 4,4-spirocyclic indol γ-lactams by tandem radical cyclization of iodoaryl allyl azides with CO was achieved. The reaction of iodoaryl allyl azides, TTMSS and AIBN under CO pressure (80 atm) in THF at 80 °C gave the desired 4,4-spirocyclic indoline, benzofuran, and oxindole γ-lactams in moderate to good yields. Beilstein-Institut 2013-07-05 /pmc/articles/PMC3740707/ /pubmed/23946829 http://dx.doi.org/10.3762/bjoc.9.151 Text en Copyright © 2013, Ueda et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Ueda, Mitsuhiro
Uenoyama, Yoshitaka
Terasoma, Nozomi
Doi, Shoko
Kobayashi, Shoji
Ryu, Ilhyong
Murphy, John A
A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide
title A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide
title_full A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide
title_fullStr A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide
title_full_unstemmed A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide
title_short A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide
title_sort construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740707/
https://www.ncbi.nlm.nih.gov/pubmed/23946829
http://dx.doi.org/10.3762/bjoc.9.151
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