Cargando…
d-Glucosamine as the Green Ligand for Cu(I)-Catalyzed Regio- and Stereoselective Domino Synthesis of (Z)-3-Methyleneisoindoline-1-ones and (E)-N-Aryl-4H-thiochromen-4-imines
[Image: see text] d-Glucosamine, a natural, inexpensive, and conveniently accessible sugar, has been explored as an efficient ligand for the Cu(I)-catalyzed regio- and stereoselective synthesis of an array of (Z)-3-methyleneisoindoline-1-ones and (E)-N-aryl-4H-thiochromen-4-imines in good-to-excelle...
Autores principales: | , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2021
|
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8375096/ https://www.ncbi.nlm.nih.gov/pubmed/34423220 http://dx.doi.org/10.1021/acsomega.1c03003 |
_version_ | 1783740251542388736 |
---|---|
author | Singh, Sumit K. Yadav, Mangal S. Singh, Anoop S. Agrahari, Anand K. Mishra, Nidhi Kumar, Sunil Tiwari, Vinod K. |
author_facet | Singh, Sumit K. Yadav, Mangal S. Singh, Anoop S. Agrahari, Anand K. Mishra, Nidhi Kumar, Sunil Tiwari, Vinod K. |
author_sort | Singh, Sumit K. |
collection | PubMed |
description | [Image: see text] d-Glucosamine, a natural, inexpensive, and conveniently accessible sugar, has been explored as an efficient ligand for the Cu(I)-catalyzed regio- and stereoselective synthesis of an array of (Z)-3-methyleneisoindoline-1-ones and (E)-N-aryl-4H-thiochromen-4-imines in good-to-excellent yield in a tandem fashion via the reaction of 2-halobenzamide and 2-halobenzothioamide with terminal alkynes, respectively. The water solubility and biocompatible nature of the ligand offer easy separation of the catalytic system toward the aqueous phase as well as change in the reaction path in terms of the product also demonstrated the variation of the reaction temperature. The domino reaction proceeds by the Sonogashira and Ullmann type cross-coupling reaction, followed by Cu(I)-promoted additive cyclization of heteroatom to the triple bond. In addition, d-glucosamine causes successful Glaser–Hay coupling of terminal alkynes under Cu catalysis to produce a high yield of respective 1,3-diynes. |
format | Online Article Text |
id | pubmed-8375096 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-83750962021-08-20 d-Glucosamine as the Green Ligand for Cu(I)-Catalyzed Regio- and Stereoselective Domino Synthesis of (Z)-3-Methyleneisoindoline-1-ones and (E)-N-Aryl-4H-thiochromen-4-imines Singh, Sumit K. Yadav, Mangal S. Singh, Anoop S. Agrahari, Anand K. Mishra, Nidhi Kumar, Sunil Tiwari, Vinod K. ACS Omega [Image: see text] d-Glucosamine, a natural, inexpensive, and conveniently accessible sugar, has been explored as an efficient ligand for the Cu(I)-catalyzed regio- and stereoselective synthesis of an array of (Z)-3-methyleneisoindoline-1-ones and (E)-N-aryl-4H-thiochromen-4-imines in good-to-excellent yield in a tandem fashion via the reaction of 2-halobenzamide and 2-halobenzothioamide with terminal alkynes, respectively. The water solubility and biocompatible nature of the ligand offer easy separation of the catalytic system toward the aqueous phase as well as change in the reaction path in terms of the product also demonstrated the variation of the reaction temperature. The domino reaction proceeds by the Sonogashira and Ullmann type cross-coupling reaction, followed by Cu(I)-promoted additive cyclization of heteroatom to the triple bond. In addition, d-glucosamine causes successful Glaser–Hay coupling of terminal alkynes under Cu catalysis to produce a high yield of respective 1,3-diynes. American Chemical Society 2021-08-04 /pmc/articles/PMC8375096/ /pubmed/34423220 http://dx.doi.org/10.1021/acsomega.1c03003 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Singh, Sumit K. Yadav, Mangal S. Singh, Anoop S. Agrahari, Anand K. Mishra, Nidhi Kumar, Sunil Tiwari, Vinod K. d-Glucosamine as the Green Ligand for Cu(I)-Catalyzed Regio- and Stereoselective Domino Synthesis of (Z)-3-Methyleneisoindoline-1-ones and (E)-N-Aryl-4H-thiochromen-4-imines |
title | d-Glucosamine as the Green Ligand
for Cu(I)-Catalyzed Regio- and Stereoselective Domino Synthesis of
(Z)-3-Methyleneisoindoline-1-ones and (E)-N-Aryl-4H-thiochromen-4-imines |
title_full | d-Glucosamine as the Green Ligand
for Cu(I)-Catalyzed Regio- and Stereoselective Domino Synthesis of
(Z)-3-Methyleneisoindoline-1-ones and (E)-N-Aryl-4H-thiochromen-4-imines |
title_fullStr | d-Glucosamine as the Green Ligand
for Cu(I)-Catalyzed Regio- and Stereoselective Domino Synthesis of
(Z)-3-Methyleneisoindoline-1-ones and (E)-N-Aryl-4H-thiochromen-4-imines |
title_full_unstemmed | d-Glucosamine as the Green Ligand
for Cu(I)-Catalyzed Regio- and Stereoselective Domino Synthesis of
(Z)-3-Methyleneisoindoline-1-ones and (E)-N-Aryl-4H-thiochromen-4-imines |
title_short | d-Glucosamine as the Green Ligand
for Cu(I)-Catalyzed Regio- and Stereoselective Domino Synthesis of
(Z)-3-Methyleneisoindoline-1-ones and (E)-N-Aryl-4H-thiochromen-4-imines |
title_sort | d-glucosamine as the green ligand
for cu(i)-catalyzed regio- and stereoselective domino synthesis of
(z)-3-methyleneisoindoline-1-ones and (e)-n-aryl-4h-thiochromen-4-imines |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8375096/ https://www.ncbi.nlm.nih.gov/pubmed/34423220 http://dx.doi.org/10.1021/acsomega.1c03003 |
work_keys_str_mv | AT singhsumitk dglucosamineasthegreenligandforcuicatalyzedregioandstereoselectivedominosynthesisofz3methyleneisoindoline1onesandenaryl4hthiochromen4imines AT yadavmangals dglucosamineasthegreenligandforcuicatalyzedregioandstereoselectivedominosynthesisofz3methyleneisoindoline1onesandenaryl4hthiochromen4imines AT singhanoops dglucosamineasthegreenligandforcuicatalyzedregioandstereoselectivedominosynthesisofz3methyleneisoindoline1onesandenaryl4hthiochromen4imines AT agraharianandk dglucosamineasthegreenligandforcuicatalyzedregioandstereoselectivedominosynthesisofz3methyleneisoindoline1onesandenaryl4hthiochromen4imines AT mishranidhi dglucosamineasthegreenligandforcuicatalyzedregioandstereoselectivedominosynthesisofz3methyleneisoindoline1onesandenaryl4hthiochromen4imines AT kumarsunil dglucosamineasthegreenligandforcuicatalyzedregioandstereoselectivedominosynthesisofz3methyleneisoindoline1onesandenaryl4hthiochromen4imines AT tiwarivinodk dglucosamineasthegreenligandforcuicatalyzedregioandstereoselectivedominosynthesisofz3methyleneisoindoline1onesandenaryl4hthiochromen4imines |