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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...

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Autores principales: Karthikeyan, Soundararajan, Shobana, Radha Krishnan, Subimol, Kamarajapurathu Raju, Monica, J Helen Ratna, Kumar, Ayyanoth Karthik Krishna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
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.
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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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