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β-Amino functionalization of cinnamic Weinreb amides in ionic liquid
2-Ns-Protected β-amino Weinreb amides were synthesized by aminochlorination of α,β-unsaturated Weinreb amides in an ionic liquid, 1-n-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([BMIM][NTf(2)]). Processed without the use of metal catalysts or the need of an inert gas atmosphere, th...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Beilstein-Institut
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238596/ https://www.ncbi.nlm.nih.gov/pubmed/28144305 http://dx.doi.org/10.3762/bjoc.12.231 |
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author | Wang, Yi-Ning Sun, Guo-Xiang Qi, Gang |
author_facet | Wang, Yi-Ning Sun, Guo-Xiang Qi, Gang |
author_sort | Wang, Yi-Ning |
collection | PubMed |
description | 2-Ns-Protected β-amino Weinreb amides were synthesized by aminochlorination of α,β-unsaturated Weinreb amides in an ionic liquid, 1-n-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([BMIM][NTf(2)]). Processed without the use of metal catalysts or the need of an inert gas atmosphere, the presented process can be readily performed as a one-pot synthesis at room temperature. Moreover, the preparation has the distinct advantages of the use of 2-NsNCl(2) as an inexpensive and stable nitrogen/halogen source and the ionic liquid as a recyclable reaction media. Nine examples were examined, and modest to good isolated chemical yields (40–83%) were obtained. |
format | Online Article Text |
id | pubmed-5238596 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-52385962017-01-31 β-Amino functionalization of cinnamic Weinreb amides in ionic liquid Wang, Yi-Ning Sun, Guo-Xiang Qi, Gang Beilstein J Org Chem Full Research Paper 2-Ns-Protected β-amino Weinreb amides were synthesized by aminochlorination of α,β-unsaturated Weinreb amides in an ionic liquid, 1-n-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([BMIM][NTf(2)]). Processed without the use of metal catalysts or the need of an inert gas atmosphere, the presented process can be readily performed as a one-pot synthesis at room temperature. Moreover, the preparation has the distinct advantages of the use of 2-NsNCl(2) as an inexpensive and stable nitrogen/halogen source and the ionic liquid as a recyclable reaction media. Nine examples were examined, and modest to good isolated chemical yields (40–83%) were obtained. Beilstein-Institut 2016-11-11 /pmc/articles/PMC5238596/ /pubmed/28144305 http://dx.doi.org/10.3762/bjoc.12.231 Text en Copyright © 2016, Wang 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), 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 | Full Research Paper Wang, Yi-Ning Sun, Guo-Xiang Qi, Gang β-Amino functionalization of cinnamic Weinreb amides in ionic liquid |
title | β-Amino functionalization of cinnamic Weinreb amides in ionic liquid |
title_full | β-Amino functionalization of cinnamic Weinreb amides in ionic liquid |
title_fullStr | β-Amino functionalization of cinnamic Weinreb amides in ionic liquid |
title_full_unstemmed | β-Amino functionalization of cinnamic Weinreb amides in ionic liquid |
title_short | β-Amino functionalization of cinnamic Weinreb amides in ionic liquid |
title_sort | β-amino functionalization of cinnamic weinreb amides in ionic liquid |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238596/ https://www.ncbi.nlm.nih.gov/pubmed/28144305 http://dx.doi.org/10.3762/bjoc.12.231 |
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