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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2020
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Materias: | |
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. |
format | Online Article Text |
id | pubmed-7113552 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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