(±)-2-{[4-(4-Bromophenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-1-phenyl-1-ethanol

Milenca Mariana Vorga,Valentin Badea

doi:10.3390/m1268

Abstract

The novel racemic secondary alcohol (±)-2-{[4-(4-bromophenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-1-phenyl-1-ethanol (12) has been successfully synthesized through S-alkylation of 4-(4-bromophenyl)-5-phenyl-4H-1,2,4-triazole-3-thiol (10) in alkaline medium with 2-bromo-1-phenylethanone followed by reduction of the corresponding ketone 11. All the synthesized compounds were characterized by IR, 1D (1H, 13C, DEPT135) and 2D (1H-1H, 1H-13C and 1H-15N) NMR spectroscopy, elemental analysis and HRMS spectrometry.

Highlights

Triazoles are an important class of compounds due to their numerous biomedical applications [1], such as antibacterial activity [2,3], antifungal [4] anticancer [5,6], antioxidant activity and anticonvulsant effects [7]
All the synthesized compounds were characterized by Infrared spectra (IR), 1D (1H, 13C, DEPT135) and 2D (1H-1H, 1H-13C and 1H-15N) NMR spectroscopy, elemental analysis and High resolution MS (HRMS) spectrometry
The required 2-acyl-N-(4-aryl)hydrazine-1-carbothioamides 3 can be obtained by reaction of the appropriate carboxylic acid hydrazides 1 withisothiocyanates 2 [16,17] or by a one-pot reaction starting from an aromatic amines 4 by successive reaction with carbon sulphide, sodium chloroacetate and hydrazine with the intermediate obtaining of N-(aryl)hydrazinecarbothioamides 5 [18,19], followed by their acylation with acyl chlorides (Scheme 1)

Summary

Introduction

Triazoles are an important class of compounds due to their numerous biomedical applications [1], such as antibacterial activity [2,3], antifungal [4] anticancer [5,6], antioxidant activity and anticonvulsant effects [7]. 4-(4-Bromophenyl)-5-phenyl-4H-1,2,4-triazole-3-thiol (10) was synthesized starting from 4-bromoaniline according to the literature methods (Scheme 2).

Results

Conclusion