Synthesis of 4-[(1H-Benzimidazol-2-yl)sulfanyl]benzaldehyde and 2-({4-[(1H-Benzimidazol-2-yl)sulfanyl]phenyl}methylidene)hydrazine-1-carbothioamide

Mustafa Turki Ubeid,Hamdy Khamees Thabet,Mohamed Yousef Abu Shuheil

doi:10.3390/m1273

Abstract

Here we describe the preparation of 2-(4-((1H-benzo[d]imidazol-2-yl)thio)-benzylidene)-hydrazine-1-carbothioamide in two steps. In the first step, 1,3-dihydro-2H-1,3-benzimidazole-2-thione was reacted with 4-fluorobenzaldehyde in DMSO to get 4-[(1H-benzimidazol-2-yl)sulfanyl]benzaldehyde in high yield. The reaction of the obtained aldehyde with thiosemicarbazide in ethanol at reflux temperature yielded 2-({4-[(1H-benzimidazol-2-yl)sulfanyl]phenyl}methylidene)hydrazine-1-carbothioamide. The structure of the synthesized compounds was established by NMR spectroscopy (1H, 13C), mass spectrometry, and infrared spectroscopy.

Highlights

Benzimidazoles are one of the important heterocyclic templates for the intensive investigation in chemical sciences due to their well-known applications and interesting biological activity profile [1,2,3,4,5,6]. Thiosemicarbazone moiety is another privileged structure that is found in several molecules with a wide range of biological activities representing several important classes in drug discovery [7,8,9,10,11,12]
Thiosemicarbazones have been postulated as biologically active compounds and display different types of biological activity, such as anticancer [11,13], anti-HIV [14,15], anticonvulsant [16,17], antimalarial [18,19], anti-inflammatory [20], enzymatic inhibition [9,10,21], antiviral [22], antioxidant [23], antifungal [24], and antibacterial [24,25]
The flexibility of thiosemicarbazones as nitrogen and sulfur donors consents them to bring on a great diversity of coordination modes [26]

Summary

Introduction

Benzimidazoles are one of the important heterocyclic templates for the intensive investigation in chemical sciences due to their well-known applications and interesting biological activity profile [1,2,3,4,5,6] Thiosemicarbazone moiety is another privileged structure that is found in several molecules with a wide range of biological activities representing several important classes in drug discovery [7,8,9,10,11,12]. The authors trust that this is the first report that discloses the synthesis and spectral analysis of 2-({4-[(1Hbenzimidazol-2-yl)sulfanyl]phenyl}methylidene)hydrazine-1-carbothioamide because the exact structure search in the SciFinder database for this compound did not provide any hit or reference.

Results and Discussion

General

C14 H10 N2 OS