Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines

Alkyl 2-diazo-3-oxoalkanoates generate alkoxycarbonylketenes, which undergo an electrophilic ring expansion with aziridines to afford alkyl 2-(oxazolin-2-yl)alkanoates in good to excellent yields under microwave heating. The method is a convenient and clean reaction without any activators and cataly...

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Autores principales: Lei, Yelong, Xu, Jiaxi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8744460/
https://www.ncbi.nlm.nih.gov/pubmed/35047083
http://dx.doi.org/10.3762/bjoc.18.6
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author Lei, Yelong
Xu, Jiaxi
author_facet Lei, Yelong
Xu, Jiaxi
author_sort Lei, Yelong
collection PubMed
description Alkyl 2-diazo-3-oxoalkanoates generate alkoxycarbonylketenes, which undergo an electrophilic ring expansion with aziridines to afford alkyl 2-(oxazolin-2-yl)alkanoates in good to excellent yields under microwave heating. The method is a convenient and clean reaction without any activators and catalysts and can be also applied in the synthesis of 2-(oxazolin-2-yl)alkanamides and 1-(oxazolin-2-yl)alkylphosphonates.
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spelling pubmed-87444602022-01-18 Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines Lei, Yelong Xu, Jiaxi Beilstein J Org Chem Full Research Paper Alkyl 2-diazo-3-oxoalkanoates generate alkoxycarbonylketenes, which undergo an electrophilic ring expansion with aziridines to afford alkyl 2-(oxazolin-2-yl)alkanoates in good to excellent yields under microwave heating. The method is a convenient and clean reaction without any activators and catalysts and can be also applied in the synthesis of 2-(oxazolin-2-yl)alkanamides and 1-(oxazolin-2-yl)alkylphosphonates. Beilstein-Institut 2022-01-05 /pmc/articles/PMC8744460/ /pubmed/35047083 http://dx.doi.org/10.3762/bjoc.18.6 Text en Copyright © 2022, Lei and Xu https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Lei, Yelong
Xu, Jiaxi
Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines
title Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines
title_full Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines
title_fullStr Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines
title_full_unstemmed Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines
title_short Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines
title_sort efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8744460/
https://www.ncbi.nlm.nih.gov/pubmed/35047083
http://dx.doi.org/10.3762/bjoc.18.6
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AT xujiaxi efficientsynthesisofethyl2oxazolin2ylalkanoatesviaethoxycarbonylketeneinducedelectrophilicringexpansionofaziridines

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