Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization

An operationally simple protocol for the synthesis of 2,3-dihydrobenzo[f][1,4]oxazepin-3-ones, based on an Ugi reaction of an ortho-(benzyloxy)benzylamine, glycolic acid, an isocyanide and an aldehyde, followed by an intramolecular Mitsunobu substitution was developed. The required ortho-(benzyloxy)...

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Detalles Bibliográficos
Autores principales: Moni, Lisa, Banfi, Luca, Basso, Andrea, Brambilla, Alice, Riva, Renata
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943941/
https://www.ncbi.nlm.nih.gov/pubmed/24605140
http://dx.doi.org/10.3762/bjoc.10.16
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author Moni, Lisa
Banfi, Luca
Basso, Andrea
Brambilla, Alice
Riva, Renata
author_facet Moni, Lisa
Banfi, Luca
Basso, Andrea
Brambilla, Alice
Riva, Renata
author_sort Moni, Lisa
collection PubMed
description An operationally simple protocol for the synthesis of 2,3-dihydrobenzo[f][1,4]oxazepin-3-ones, based on an Ugi reaction of an ortho-(benzyloxy)benzylamine, glycolic acid, an isocyanide and an aldehyde, followed by an intramolecular Mitsunobu substitution was developed. The required ortho-(benzyloxy)benzylamines have been in situ generated from the corresponding azides, in turn prepared in high yields from salicylic derivatives.
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spelling pubmed-39439412014-03-06 Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization Moni, Lisa Banfi, Luca Basso, Andrea Brambilla, Alice Riva, Renata Beilstein J Org Chem Letter An operationally simple protocol for the synthesis of 2,3-dihydrobenzo[f][1,4]oxazepin-3-ones, based on an Ugi reaction of an ortho-(benzyloxy)benzylamine, glycolic acid, an isocyanide and an aldehyde, followed by an intramolecular Mitsunobu substitution was developed. The required ortho-(benzyloxy)benzylamines have been in situ generated from the corresponding azides, in turn prepared in high yields from salicylic derivatives. Beilstein-Institut 2014-01-17 /pmc/articles/PMC3943941/ /pubmed/24605140 http://dx.doi.org/10.3762/bjoc.10.16 Text en Copyright © 2014, Moni 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
Moni, Lisa
Banfi, Luca
Basso, Andrea
Brambilla, Alice
Riva, Renata
Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title_full Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title_fullStr Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title_full_unstemmed Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title_short Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title_sort diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the ugi multicomponent reaction with a mitsunobu cyclization
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943941/
https://www.ncbi.nlm.nih.gov/pubmed/24605140
http://dx.doi.org/10.3762/bjoc.10.16
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