Synthesis of Some New 1,3,4-Thiadiazole, Thiazole and Pyridine Derivatives Containing 1,2,3-Triazole Moiety.

Nadia Abdelriheem,Ali Mohamed,Abdou Abdelhamid

doi:10.3390/molecules22020268

Abstract

In this study, 1-(5-Methyl-1-(p-tolyl)-1H-1,2,3-triazol-4-yl)ethan-1-one, was reacted with Thiosemicarbazide, alkyl carbodithioate and benzaldehyde to give thiosemicarbazone, alkylidenehydrazinecarbodithioate and 3-phenylprop-2-en-1-one-1,2,3-triazole derivatives. The 1,3,4-thiadiazole derivatives containing the 1,2,3-triazole moiety were obtained via reaction of alkylidenecarbodithioate with hydrazonoyl halides. Also, hydrazonoyl halides were reacted with thiosemicarbazone and pyrazolylthioamide to give 1,3-thiazoles derivatives. Subsequently, 3-phenyl-2-en-1-one was used to synthesize substituted pyridines and substituted nicotinic acid ester. The latter was converted to its azide compound which was reacted with aromatic amines and phenol to give substituted urea and phenylcarbamate containing 1,2,3-triazole moiety. The newly synthesized compounds were established by elemental analysis, spectral data and alternative synthesis whenever possible.

Highlights

1,2,3-triazoles are useful building blocks and are important due to their broad range of biological activities [1,2]—they are stable to moisture, oxygen, light and metabolic process
We report here the synthesis of new 1,3,4-thiadiazoles, 5-arylazothiazoles, and pyridines containing 1,2,3-triazole moiety
(3a) in ethanolic triethylamine at room temperature oneethyl isolated product formulated as ethyl 5-((1-(5-methyl-1-(p-tolyl)-1H-1,2,3at room temperature gave one isolated product formulated as ethyl 5-((1-(5-methyl-1-(p-tolyl)-1H-1,2,3triazol-4-yl)ethylidene)-hydrazono)-4-phenyl-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate

Summary

Introduction

1,2,3-triazoles are useful building blocks and are important due to their broad range of biological activities [1,2]—they are stable to moisture, oxygen, light and metabolic process. Thiazoles display a broad range of biological activities and are found in many potent biologically active molecules such as antimicrobial, antifungal and antineoplastic drugs [6]. They are mostly known for their anticancer [7] and antimicrobial [8] activities. Pyridine derivatives, including those bearing various heterocyclic nuclei, have shown potent pharmacological properties, including antifungal [9,10], antitubercular [11], antimalarial [12], antibacterial [13], antimicrobial [14], or insecticide [15]. We report here the synthesis of new 1,3,4-thiadiazoles, 5-arylazothiazoles, and pyridines containing 1,2,3-triazole moiety

Results

Materials and Methods

Conclusions