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Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts
The direct transformation of Morita–Baylis–Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising...
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/PMC7356223/ https://www.ncbi.nlm.nih.gov/pubmed/32704324 http://dx.doi.org/10.3762/bjoc.16.130 |
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author | Karthikeyan, Soundararajan Shobana, Radha Krishnan Subimol, Kamarajapurathu Raju Monica, J Helen Ratna Kumar, Ayyanoth Karthik Krishna |
author_facet | Karthikeyan, Soundararajan Shobana, Radha Krishnan Subimol, Kamarajapurathu Raju Monica, J Helen Ratna Kumar, Ayyanoth Karthik Krishna |
author_sort | Karthikeyan, Soundararajan |
collection | PubMed |
description | The direct transformation of Morita–Baylis–Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising structurally demanding (E)/(Z)-cinnamyl-1H-1,2,3-triazoles and halomethylcoumarins from MBH adducts. The novel methodology, efficient catalyst, and direct utilization of MBH adducts under mild reaction conditions qualify the reported procedures as powerful synthetic tools. |
format | Online Article Text |
id | pubmed-7356223 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-73562232020-07-22 Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts Karthikeyan, Soundararajan Shobana, Radha Krishnan Subimol, Kamarajapurathu Raju Monica, J Helen Ratna Kumar, Ayyanoth Karthik Krishna Beilstein J Org Chem Full Research Paper The direct transformation of Morita–Baylis–Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising structurally demanding (E)/(Z)-cinnamyl-1H-1,2,3-triazoles and halomethylcoumarins from MBH adducts. The novel methodology, efficient catalyst, and direct utilization of MBH adducts under mild reaction conditions qualify the reported procedures as powerful synthetic tools. Beilstein-Institut 2020-07-01 /pmc/articles/PMC7356223/ /pubmed/32704324 http://dx.doi.org/10.3762/bjoc.16.130 Text en Copyright © 2020, Karthikeyan 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 Karthikeyan, Soundararajan Shobana, Radha Krishnan Subimol, Kamarajapurathu Raju Monica, J Helen Ratna Kumar, Ayyanoth Karthik Krishna Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts |
title | Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts |
title_full | Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts |
title_fullStr | Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts |
title_full_unstemmed | Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts |
title_short | Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts |
title_sort | azidophosphonium salt-directed chemoselective synthesis of (e)/(z)-cinnamyl-1h-triazoles and regiospecific access to bromomethylcoumarins from morita–baylis–hillman adducts |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7356223/ https://www.ncbi.nlm.nih.gov/pubmed/32704324 http://dx.doi.org/10.3762/bjoc.16.130 |
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