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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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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. |
format | Online Article Text |
id | pubmed-9050572 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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