An improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines

A concise synthetic route was designed for making telmisartan. The key bis-benzimidazole structure was constructed via the copper-catalyzed cyclization of o-haloarylamidines. By adopting this approach, telmisartan was obtained in a 7-step overall yield of 54% starting from commercially available 3-m...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhang, Junchi, Li, Rui, Zhu, Fuqiang, Sun, Changliang, Shen, Jingshan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9051534/
https://www.ncbi.nlm.nih.gov/pubmed/35493026
http://dx.doi.org/10.1039/d0ra00886a
_version_ 1784696580063887360
author Zhang, Junchi
Li, Rui
Zhu, Fuqiang
Sun, Changliang
Shen, Jingshan
author_facet Zhang, Junchi
Li, Rui
Zhu, Fuqiang
Sun, Changliang
Shen, Jingshan
author_sort Zhang, Junchi
collection PubMed
description A concise synthetic route was designed for making telmisartan. The key bis-benzimidazole structure was constructed via the copper-catalyzed cyclization of o-haloarylamidines. By adopting this approach, telmisartan was obtained in a 7-step overall yield of 54% starting from commercially available 3-methyl-4-nitrobenzoic acid, and the use of HNO(3)/H(2)SO(4) for nitration and polyphosphoric acid (PPA) for cyclization in the reported literatures were avoided.
format Online
Article
Text
id pubmed-9051534
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90515342022-04-29 An improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines Zhang, Junchi Li, Rui Zhu, Fuqiang Sun, Changliang Shen, Jingshan RSC Adv Chemistry A concise synthetic route was designed for making telmisartan. The key bis-benzimidazole structure was constructed via the copper-catalyzed cyclization of o-haloarylamidines. By adopting this approach, telmisartan was obtained in a 7-step overall yield of 54% starting from commercially available 3-methyl-4-nitrobenzoic acid, and the use of HNO(3)/H(2)SO(4) for nitration and polyphosphoric acid (PPA) for cyclization in the reported literatures were avoided. The Royal Society of Chemistry 2020-04-03 /pmc/articles/PMC9051534/ /pubmed/35493026 http://dx.doi.org/10.1039/d0ra00886a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Zhang, Junchi
Li, Rui
Zhu, Fuqiang
Sun, Changliang
Shen, Jingshan
An improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines
title An improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines
title_full An improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines
title_fullStr An improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines
title_full_unstemmed An improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines
title_short An improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines
title_sort improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9051534/
https://www.ncbi.nlm.nih.gov/pubmed/35493026
http://dx.doi.org/10.1039/d0ra00886a
work_keys_str_mv AT zhangjunchi animprovedsynthesisoftelmisartanviathecoppercatalyzedcyclizationofohaloarylamidines
AT lirui animprovedsynthesisoftelmisartanviathecoppercatalyzedcyclizationofohaloarylamidines
AT zhufuqiang animprovedsynthesisoftelmisartanviathecoppercatalyzedcyclizationofohaloarylamidines
AT sunchangliang animprovedsynthesisoftelmisartanviathecoppercatalyzedcyclizationofohaloarylamidines
AT shenjingshan animprovedsynthesisoftelmisartanviathecoppercatalyzedcyclizationofohaloarylamidines
AT zhangjunchi improvedsynthesisoftelmisartanviathecoppercatalyzedcyclizationofohaloarylamidines
AT lirui improvedsynthesisoftelmisartanviathecoppercatalyzedcyclizationofohaloarylamidines
AT zhufuqiang improvedsynthesisoftelmisartanviathecoppercatalyzedcyclizationofohaloarylamidines
AT sunchangliang improvedsynthesisoftelmisartanviathecoppercatalyzedcyclizationofohaloarylamidines
AT shenjingshan improvedsynthesisoftelmisartanviathecoppercatalyzedcyclizationofohaloarylamidines

Ejemplares similares