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Functionalization of C–H bonds in acetophenone oximes with arylacetic acids and elemental sulfur

Fused thieno[3,2-d]thiazoles were synthesized via a coupling of acetophenone ketoximes, arylacetic acids, and elemental sulfur in the presence of Li(2)CO(3) base. Functionalities including chloro, bromo, fluoro, trifluoromethyl, and pyridyl groups were compatible with reaction conditions. High yield...

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Detalles Bibliográficos
Autores principales: Pham, Phuc H., Nguyen, Khang X., Pham, Hoai T. B., Tran, Thien T., Nguyen, Tung T., Phan, Nam T. S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9050572/
https://www.ncbi.nlm.nih.gov/pubmed/35495317
http://dx.doi.org/10.1039/d0ra00808g
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author Pham, Phuc H.
Nguyen, Khang X.
Pham, Hoai T. B.
Tran, Thien T.
Nguyen, Tung T.
Phan, Nam T. S.
author_facet Pham, Phuc H.
Nguyen, Khang X.
Pham, Hoai T. B.
Tran, Thien T.
Nguyen, Tung T.
Phan, Nam T. S.
author_sort Pham, Phuc H.
collection PubMed
description Fused thieno[3,2-d]thiazoles were synthesized via a coupling of acetophenone ketoximes, arylacetic acids, and elemental sulfur in the presence of Li(2)CO(3) base. Functionalities including chloro, bromo, fluoro, trifluoromethyl, and pyridyl groups were compatible with reaction conditions. High yields and excellent regioselectivities were obtained even if meta-substituted ketoxime acetates were used. Ethyl esters of heteroarylacetic acids were competent substrates, which is very rare in the literature. Our method would offer a convenient protocol to afford polyheterocyclic structures from simple substrates.
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spelling pubmed-90505722022-04-29 Functionalization of C–H bonds in acetophenone oximes with arylacetic acids and elemental sulfur Pham, Phuc H. Nguyen, Khang X. Pham, Hoai T. B. Tran, Thien T. Nguyen, Tung T. Phan, Nam T. S. RSC Adv Chemistry Fused thieno[3,2-d]thiazoles were synthesized via a coupling of acetophenone ketoximes, arylacetic acids, and elemental sulfur in the presence of Li(2)CO(3) base. Functionalities including chloro, bromo, fluoro, trifluoromethyl, and pyridyl groups were compatible with reaction conditions. High yields and excellent regioselectivities were obtained even if meta-substituted ketoxime acetates were used. Ethyl esters of heteroarylacetic acids were competent substrates, which is very rare in the literature. Our method would offer a convenient protocol to afford polyheterocyclic structures from simple substrates. The Royal Society of Chemistry 2020-03-17 /pmc/articles/PMC9050572/ /pubmed/35495317 http://dx.doi.org/10.1039/d0ra00808g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Pham, Phuc H.
Nguyen, Khang X.
Pham, Hoai T. B.
Tran, Thien T.
Nguyen, Tung T.
Phan, Nam T. S.
Functionalization of C–H bonds in acetophenone oximes with arylacetic acids and elemental sulfur
title Functionalization of C–H bonds in acetophenone oximes with arylacetic acids and elemental sulfur
title_full Functionalization of C–H bonds in acetophenone oximes with arylacetic acids and elemental sulfur
title_fullStr Functionalization of C–H bonds in acetophenone oximes with arylacetic acids and elemental sulfur
title_full_unstemmed Functionalization of C–H bonds in acetophenone oximes with arylacetic acids and elemental sulfur
title_short Functionalization of C–H bonds in acetophenone oximes with arylacetic acids and elemental sulfur
title_sort functionalization of c–h bonds in acetophenone oximes with arylacetic acids and elemental sulfur
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9050572/
https://www.ncbi.nlm.nih.gov/pubmed/35495317
http://dx.doi.org/10.1039/d0ra00808g
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