(R,S)-2-{[4-(4-Methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol

Vladislav-Silvestru Valicsek,Valentin Badea

doi:10.3390/m1241

Abstract

4-(4-Methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-thiol (4) was alkylated to 2-{[4-(4-methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]thio}-1-phenylethan-1-one (5) in alkaline conditions using 2-bromo-1-phenylethanone. The alkylated compound (5) was reduced at the carbonyl group to the corresponding racemic secondary alcohol with an asymmetric carbon, (R,S)-2-{[4-(4-methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol (6). Both synthesized compounds, ketone (5) and secondary alcohol (6), are new and have not yet been reported in the literature. All the synthesized compounds were characterized by IR, 1D and 2D 1H-1H, 1H-13C and 1H-15N NMR spectroscopy and by elemental analysis.

Highlights

Introduction4-(4-Methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-thiol4‐(4‐Methylphenyl)‐5‐phenyl‐4H‐1,2,4‐triazol‐3‐thiol (4) was was synthesized synthesized starting starting from from4-methylaniline4‐methylaniline(1)(1)via viathe thecorresponding correspondingN-(4-methylphenyl)hydrazinecarbothioaN‐(4‐methylphenyl)hydrazinecarbothio‐mide (2), followed byby acylation toto2-benzoyl-N-(4-methylphenyl)hydrazine-1-carbothioa amide (2), followed acylation2‐benzoyl‐N‐(4‐methylphenyl)hydrazine‐1‐carbothio‐ (3)and cyclization of to
Tant element in the synthesis andand design of of bioactive compounds, portant element in the synthesis design bioactive compounds,which whichare areassociated associated with biological activities
The equilibrium shift to tautomeric thione form

Summary

Introduction

4‐(4‐Methylphenyl)‐5‐phenyl‐4H‐1,2,4‐triazol‐3‐thiol (4) was was synthesized synthesized starting starting from from4-methylaniline. 4-(4-methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-thiol amide (3) and cyclization of (3) to 4‐(4‐methylphenyl)‐5‐phenyl‐4H‐1,2,4‐triazol‐3‐thiol(4). S-alkylation waswas performed using accordingtotothe theliterature literature methods. Cesium carbonate as a base [6,7],[6,7], and and the reduction of ketones group to the corresponding ing cesium carbonate as a base the reduction of ketones group to the correspond‐. Secondary alcohol was carried out with sodium borohydride [8]. Ing secondary alcohol was carried out with sodium borohydride [8]. With regard toNote: jurisdictional claims in tral with regard to jurisdictional published maps and institutional affilclaims in published maps and institu‐

HCl aq SH

Results and

Calculated

H-15 N spectrum of

Materials and Methods