KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones

An efficient and simple KOt-Bu-promoted selective ring-opening N-alkylation of 2-methyl-2-oxazoline or 2-(methylthio)-4,5-dihydrothiazole with benzyl halides under basic conditions is described for the first time. The method provides a convenient and practical pathway for the synthesis of versatile...

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Detalles Bibliográficos
Autores principales: Lin, Qiao, Zhang, Shiling, Li, Bin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7113552/
https://www.ncbi.nlm.nih.gov/pubmed/32273909
http://dx.doi.org/10.3762/bjoc.16.44
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author Lin, Qiao
Zhang, Shiling
Li, Bin
author_facet Lin, Qiao
Zhang, Shiling
Li, Bin
author_sort Lin, Qiao
collection PubMed
description An efficient and simple KOt-Bu-promoted selective ring-opening N-alkylation of 2-methyl-2-oxazoline or 2-(methylthio)-4,5-dihydrothiazole with benzyl halides under basic conditions is described for the first time. The method provides a convenient and practical pathway for the synthesis of versatile 2-aminoethyl acetates and N-substituted thiazolidinones with good functional group tolerance and selectivity. KOt-Bu not only plays an important role to promote this ring-opening N-alkylation, but also acts as an oxygen donor.
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spelling pubmed-71135522020-04-09 KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones Lin, Qiao Zhang, Shiling Li, Bin Beilstein J Org Chem Full Research Paper An efficient and simple KOt-Bu-promoted selective ring-opening N-alkylation of 2-methyl-2-oxazoline or 2-(methylthio)-4,5-dihydrothiazole with benzyl halides under basic conditions is described for the first time. The method provides a convenient and practical pathway for the synthesis of versatile 2-aminoethyl acetates and N-substituted thiazolidinones with good functional group tolerance and selectivity. KOt-Bu not only plays an important role to promote this ring-opening N-alkylation, but also acts as an oxygen donor. Beilstein-Institut 2020-03-25 /pmc/articles/PMC7113552/ /pubmed/32273909 http://dx.doi.org/10.3762/bjoc.16.44 Text en Copyright © 2020, Lin et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Lin, Qiao
Zhang, Shiling
Li, Bin
KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones
title KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones
title_full KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones
title_fullStr KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones
title_full_unstemmed KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones
title_short KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones
title_sort kot-bu-promoted selective ring-opening n-alkylation of 2-oxazolines to access 2-aminoethyl acetates and n-substituted thiazolidinones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7113552/
https://www.ncbi.nlm.nih.gov/pubmed/32273909
http://dx.doi.org/10.3762/bjoc.16.44
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