PhICl(2)-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins

The application of PhICl(2)/NH(4)SCN and PhICl(2)/KSeCN reagent systems to the synthesis of the biologically active S/SeCN-containing isocoumarins via a process involving thio/selenocyanation, enabled by thio/selenocyanogen chloride generated in situ, followed with an intramolecular lactonization wa...

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Autores principales: Tao, Shanqing, Huo, Aiwen, Gao, Yan, Zhang, Xiangyang, Yang, Jingyue, Du, Yunfei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9158338/
https://www.ncbi.nlm.nih.gov/pubmed/35665060
http://dx.doi.org/10.3389/fchem.2022.859995
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author Tao, Shanqing
Huo, Aiwen
Gao, Yan
Zhang, Xiangyang
Yang, Jingyue
Du, Yunfei
author_facet Tao, Shanqing
Huo, Aiwen
Gao, Yan
Zhang, Xiangyang
Yang, Jingyue
Du, Yunfei
author_sort Tao, Shanqing
collection PubMed
description The application of PhICl(2)/NH(4)SCN and PhICl(2)/KSeCN reagent systems to the synthesis of the biologically active S/SeCN-containing isocoumarins via a process involving thio/selenocyanation, enabled by thio/selenocyanogen chloride generated in situ, followed with an intramolecular lactonization was realized. Gram-scale synthesis, further derivatization to access C4 thio/selenocyanated Xyridin A and anti-tumor activities of the obtained products highlight the potential use of this method.
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spelling pubmed-91583382022-06-02 PhICl(2)-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins Tao, Shanqing Huo, Aiwen Gao, Yan Zhang, Xiangyang Yang, Jingyue Du, Yunfei Front Chem Chemistry The application of PhICl(2)/NH(4)SCN and PhICl(2)/KSeCN reagent systems to the synthesis of the biologically active S/SeCN-containing isocoumarins via a process involving thio/selenocyanation, enabled by thio/selenocyanogen chloride generated in situ, followed with an intramolecular lactonization was realized. Gram-scale synthesis, further derivatization to access C4 thio/selenocyanated Xyridin A and anti-tumor activities of the obtained products highlight the potential use of this method. Frontiers Media S.A. 2022-05-18 /pmc/articles/PMC9158338/ /pubmed/35665060 http://dx.doi.org/10.3389/fchem.2022.859995 Text en Copyright © 2022 Tao, Huo, Gao, Zhang, Yang and Du. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Tao, Shanqing
Huo, Aiwen
Gao, Yan
Zhang, Xiangyang
Yang, Jingyue
Du, Yunfei
PhICl(2)-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins
title PhICl(2)-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins
title_full PhICl(2)-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins
title_fullStr PhICl(2)-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins
title_full_unstemmed PhICl(2)-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins
title_short PhICl(2)-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins
title_sort phicl(2)-mediated regioselective and electrophilic oxythio/selenocyanation of o-(1-alkynyl)benzoates: access to biologically active s/secn-containing isocoumarins
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9158338/
https://www.ncbi.nlm.nih.gov/pubmed/35665060
http://dx.doi.org/10.3389/fchem.2022.859995
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