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

Abstract

A new and efficient method for the synthesis of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-alkyl-1H-[1,2,3]-triazoles by the room temperature 1,3-dipolarcycloaddition of (2-azido-1,3-dichloro-5-trifluoromethyl)benzene with terminal alkynes inthe presence of Cu (I) salt as catalyst is reported. All the reactions gave 1,4-disubstitutedproducts with high regioselectivity, as no 1,5-disubstituted product was formed. Thestructures of all the title compounds have been confirmed by elemental analysis, 1H- and13C-NMR and in addition, the structure of compound 5a was investigated by X-raycrystallography.

Keywords

• 1
• 3-Dipolar cycloaddition
• 1
• 2
• 3-triazole
• internal alkyne
• regioselective