Regioselective Synthesis of 1-(2,6-Dichloro-4-Trifluoromethyl-phenyl)-4-Alkyl-1H-[1,2,3]-Triazoles

A new and efficient method for the synthesis of 1-(2,6-dichloro-4-trifluoro-methylphenyl)-4-alkyl-1H-[1,2,3]-triazoles by the room temperature 1,3-dipolar cycloaddition of (2-azido-1,3-dichloro-5-trifluoromethyl)benzene with terminal alkynes in the presence of Cu (I) salt as catalyst is reported. Al...

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Autores principales: Hu, Huanan, Zhang, Anjiang, Ding, Lisheng, Lei, Xinxiang, Zhang, Lixue
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6244963/
https://www.ncbi.nlm.nih.gov/pubmed/18463565
http://dx.doi.org/10.3390/molecules13030556
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author Hu, Huanan
Zhang, Anjiang
Ding, Lisheng
Lei, Xinxiang
Zhang, Lixue
author_facet Hu, Huanan
Zhang, Anjiang
Ding, Lisheng
Lei, Xinxiang
Zhang, Lixue
author_sort Hu, Huanan
collection PubMed
description A new and efficient method for the synthesis of 1-(2,6-dichloro-4-trifluoro-methylphenyl)-4-alkyl-1H-[1,2,3]-triazoles by the room temperature 1,3-dipolar cycloaddition of (2-azido-1,3-dichloro-5-trifluoromethyl)benzene with terminal alkynes in the presence of Cu (I) salt as catalyst is reported. All the reactions gave 1,4-disubstituted products with high regioselectivity, as no 1,5-disubstituted product was formed. The structures of all the title compounds have been confirmed by elemental analysis, (1)H- and (13)C-NMR and in addition, the structure of compound 5a was investigated by X-ray crystallography.
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spelling pubmed-62449632018-11-26 Regioselective Synthesis of 1-(2,6-Dichloro-4-Trifluoromethyl-phenyl)-4-Alkyl-1H-[1,2,3]-Triazoles Hu, Huanan Zhang, Anjiang Ding, Lisheng Lei, Xinxiang Zhang, Lixue Molecules Full Paper A new and efficient method for the synthesis of 1-(2,6-dichloro-4-trifluoro-methylphenyl)-4-alkyl-1H-[1,2,3]-triazoles by the room temperature 1,3-dipolar cycloaddition of (2-azido-1,3-dichloro-5-trifluoromethyl)benzene with terminal alkynes in the presence of Cu (I) salt as catalyst is reported. All the reactions gave 1,4-disubstituted products with high regioselectivity, as no 1,5-disubstituted product was formed. The structures of all the title compounds have been confirmed by elemental analysis, (1)H- and (13)C-NMR and in addition, the structure of compound 5a was investigated by X-ray crystallography. MDPI 2008-03-03 /pmc/articles/PMC6244963/ /pubmed/18463565 http://dx.doi.org/10.3390/molecules13030556 Text en © 2008 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Full Paper
Hu, Huanan
Zhang, Anjiang
Ding, Lisheng
Lei, Xinxiang
Zhang, Lixue
Regioselective Synthesis of 1-(2,6-Dichloro-4-Trifluoromethyl-phenyl)-4-Alkyl-1H-[1,2,3]-Triazoles
title Regioselective Synthesis of 1-(2,6-Dichloro-4-Trifluoromethyl-phenyl)-4-Alkyl-1H-[1,2,3]-Triazoles
title_full Regioselective Synthesis of 1-(2,6-Dichloro-4-Trifluoromethyl-phenyl)-4-Alkyl-1H-[1,2,3]-Triazoles
title_fullStr Regioselective Synthesis of 1-(2,6-Dichloro-4-Trifluoromethyl-phenyl)-4-Alkyl-1H-[1,2,3]-Triazoles
title_full_unstemmed Regioselective Synthesis of 1-(2,6-Dichloro-4-Trifluoromethyl-phenyl)-4-Alkyl-1H-[1,2,3]-Triazoles
title_short Regioselective Synthesis of 1-(2,6-Dichloro-4-Trifluoromethyl-phenyl)-4-Alkyl-1H-[1,2,3]-Triazoles
title_sort regioselective synthesis of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-alkyl-1h-[1,2,3]-triazoles
topic Full Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6244963/
https://www.ncbi.nlm.nih.gov/pubmed/18463565
http://dx.doi.org/10.3390/molecules13030556
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