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Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes

Using N-sulfonyl triazoles as substrates, compounds as diverse as 2-imino tetrahydrofurans, 13- and 15-membered ring aza-macrocycles can be prepared selectively via formal [1 + 4], [5 + 4 + 4] and [3 + 4 + 4 + 4] condensations of α-imino carbenes and oxetanes under Rh(ii)-catalysis or thermal activa...

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Autores principales: Guarnieri-Ibáñez, Alejandro, Medina, Florian, Besnard, Céline, Kidd, Sarah L., Spring, David R., Lacour, Jérôme
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5621157/
https://www.ncbi.nlm.nih.gov/pubmed/28989611
http://dx.doi.org/10.1039/c7sc00964j
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author Guarnieri-Ibáñez, Alejandro
Medina, Florian
Besnard, Céline
Kidd, Sarah L.
Spring, David R.
Lacour, Jérôme
author_facet Guarnieri-Ibáñez, Alejandro
Medina, Florian
Besnard, Céline
Kidd, Sarah L.
Spring, David R.
Lacour, Jérôme
author_sort Guarnieri-Ibáñez, Alejandro
collection PubMed
description Using N-sulfonyl triazoles as substrates, compounds as diverse as 2-imino tetrahydrofurans, 13- and 15-membered ring aza-macrocycles can be prepared selectively via formal [1 + 4], [5 + 4 + 4] and [3 + 4 + 4 + 4] condensations of α-imino carbenes and oxetanes under Rh(ii)-catalysis or thermal activation. Spirocyclic N-heterocycles are also accessible by means of Buchwald–Hartwig and Pictet–Spengler cyclizations. By reaction control, substrate selection or further derivatization, a large variety of chemical structures is thus achievable. Finally, using triazoles reacting under thermal activation, interesting mechanistic insight was obtained.
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spelling pubmed-56211572017-10-06 Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes Guarnieri-Ibáñez, Alejandro Medina, Florian Besnard, Céline Kidd, Sarah L. Spring, David R. Lacour, Jérôme Chem Sci Chemistry Using N-sulfonyl triazoles as substrates, compounds as diverse as 2-imino tetrahydrofurans, 13- and 15-membered ring aza-macrocycles can be prepared selectively via formal [1 + 4], [5 + 4 + 4] and [3 + 4 + 4 + 4] condensations of α-imino carbenes and oxetanes under Rh(ii)-catalysis or thermal activation. Spirocyclic N-heterocycles are also accessible by means of Buchwald–Hartwig and Pictet–Spengler cyclizations. By reaction control, substrate selection or further derivatization, a large variety of chemical structures is thus achievable. Finally, using triazoles reacting under thermal activation, interesting mechanistic insight was obtained. Royal Society of Chemistry 2017-08-01 2017-06-12 /pmc/articles/PMC5621157/ /pubmed/28989611 http://dx.doi.org/10.1039/c7sc00964j Text en This journal is © The Royal Society of Chemistry 2017 https://creativecommons.org/licenses/by/3.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/ (https://creativecommons.org/licenses/by/3.0/) ) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Guarnieri-Ibáñez, Alejandro
Medina, Florian
Besnard, Céline
Kidd, Sarah L.
Spring, David R.
Lacour, Jérôme
Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes
title Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes
title_full Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes
title_fullStr Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes
title_full_unstemmed Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes
title_short Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes
title_sort diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5621157/
https://www.ncbi.nlm.nih.gov/pubmed/28989611
http://dx.doi.org/10.1039/c7sc00964j
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