Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines

It was found that 4-hydroxy-2-butenoic ester (11) could not react with 3,4-dihydro-isoquinoline (4a). Individual addition reactions of γ-mercapto-α,β-unsaturated esters (18) and -unsaturated amide (19) with 3,4-dihydroisoquinolines (4) were carried out under appropriate conditions to provide the cor...

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Autores principales: Huang, Sheng-Han, Huang, Wan-Yu, Zhang, Guo-Lun, Yang, Te-Fang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8537374/
https://www.ncbi.nlm.nih.gov/pubmed/34684705
http://dx.doi.org/10.3390/molecules26206126
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author Huang, Sheng-Han
Huang, Wan-Yu
Zhang, Guo-Lun
Yang, Te-Fang
author_facet Huang, Sheng-Han
Huang, Wan-Yu
Zhang, Guo-Lun
Yang, Te-Fang
author_sort Huang, Sheng-Han
collection PubMed
description It was found that 4-hydroxy-2-butenoic ester (11) could not react with 3,4-dihydro-isoquinoline (4a). Individual addition reactions of γ-mercapto-α,β-unsaturated esters (18) and -unsaturated amide (19) with 3,4-dihydroisoquinolines (4) were carried out under appropriate conditions to provide the corresponding thiazolo[2,3-α]isoquinoline derivatives with good yields (up to 87%) and significant diastereomeric selectivity. The mechanism of the crucial reaction was discussed.
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spelling pubmed-85373742021-10-24 Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines Huang, Sheng-Han Huang, Wan-Yu Zhang, Guo-Lun Yang, Te-Fang Molecules Communication It was found that 4-hydroxy-2-butenoic ester (11) could not react with 3,4-dihydro-isoquinoline (4a). Individual addition reactions of γ-mercapto-α,β-unsaturated esters (18) and -unsaturated amide (19) with 3,4-dihydroisoquinolines (4) were carried out under appropriate conditions to provide the corresponding thiazolo[2,3-α]isoquinoline derivatives with good yields (up to 87%) and significant diastereomeric selectivity. The mechanism of the crucial reaction was discussed. MDPI 2021-10-11 /pmc/articles/PMC8537374/ /pubmed/34684705 http://dx.doi.org/10.3390/molecules26206126 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Huang, Sheng-Han
Huang, Wan-Yu
Zhang, Guo-Lun
Yang, Te-Fang
Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines
title Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines
title_full Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines
title_fullStr Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines
title_full_unstemmed Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines
title_short Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines
title_sort facile synthesis of 3-substituted thiazolo[2,3-α]tetrahydroisoquinolines
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8537374/
https://www.ncbi.nlm.nih.gov/pubmed/34684705
http://dx.doi.org/10.3390/molecules26206126
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