Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Wang, Yi-Ning, Sun, Guo-Xiang, Qi, Gang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
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
_version_ 1782495733629321216
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
work_keys_str_mv AT wangyining baminofunctionalizationofcinnamicweinrebamidesinionicliquid
AT sunguoxiang baminofunctionalizationofcinnamicweinrebamidesinionicliquid
AT qigang baminofunctionalizationofcinnamicweinrebamidesinionicliquid