Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

A practically convenient and streamlined protocol for the trans-diastereoselective introduction of an aryl substituent at position 4 of the 1,4-dihydroisoquinol-3-one (1,4-DHIQ) scaffold is presented. The protocol involves direct Regitz diazo transfer onto readily available 3(2H)-isoquinolones follo...

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Autores principales: Dar’in, Dmitry, Kantin, Grigory, Bunev, Alexander, Krasavin, Mikhail
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9443417/
https://www.ncbi.nlm.nih.gov/pubmed/36105725
http://dx.doi.org/10.3762/bjoc.18.109
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author Dar’in, Dmitry
Kantin, Grigory
Bunev, Alexander
Krasavin, Mikhail
author_facet Dar’in, Dmitry
Kantin, Grigory
Bunev, Alexander
Krasavin, Mikhail
author_sort Dar’in, Dmitry
collection PubMed
description A practically convenient and streamlined protocol for the trans-diastereoselective introduction of an aryl substituent at position 4 of the 1,4-dihydroisoquinol-3-one (1,4-DHIQ) scaffold is presented. The protocol involves direct Regitz diazo transfer onto readily available 3(2H)-isoquinolones followed by TfOH-promoted hydroarylation by an arene molecule. Screening of the novel 1,2,4-trisubstituted 1,4-DHIQs against cancer cell lines confirmed high cytotoxicity of selected analogs, which validates this new chemotype for further investigations as anticancer cytotoxic agents.
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spelling pubmed-94434172022-09-13 Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold Dar’in, Dmitry Kantin, Grigory Bunev, Alexander Krasavin, Mikhail Beilstein J Org Chem Letter A practically convenient and streamlined protocol for the trans-diastereoselective introduction of an aryl substituent at position 4 of the 1,4-dihydroisoquinol-3-one (1,4-DHIQ) scaffold is presented. The protocol involves direct Regitz diazo transfer onto readily available 3(2H)-isoquinolones followed by TfOH-promoted hydroarylation by an arene molecule. Screening of the novel 1,2,4-trisubstituted 1,4-DHIQs against cancer cell lines confirmed high cytotoxicity of selected analogs, which validates this new chemotype for further investigations as anticancer cytotoxic agents. Beilstein-Institut 2022-08-22 /pmc/articles/PMC9443417/ /pubmed/36105725 http://dx.doi.org/10.3762/bjoc.18.109 Text en Copyright © 2022, Dar’in et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Letter
Dar’in, Dmitry
Kantin, Grigory
Bunev, Alexander
Krasavin, Mikhail
Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold
title Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold
title_full Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold
title_fullStr Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold
title_full_unstemmed Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold
title_short Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold
title_sort facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2h)-one scaffold
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9443417/
https://www.ncbi.nlm.nih.gov/pubmed/36105725
http://dx.doi.org/10.3762/bjoc.18.109
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