An NMR Study of A Novel 1,3,4-Oxadiazole Derivative Containing Benzimidazole Moiety

Abstract

Abstract:

A new compound, N-phenyl-2-({5-[(2-(phenoxymethyl)-benzimidazol-1-yl)methyl]-1, 3, 4-oxadiazol-2-yl}thio) acetamide (3), was synthesized by the reaction of 5-{[2-(phenoxymethyl)-benzimidazol-1-yl]methyl}-2-thiol-1,3, 4-oxadiazole (2) with N-phenyl-2-chloro-acetamide. The compound 2 was obtained by the reaction of the hydrazide (1) with carbon disulfide in the presence of absolute ethanol and potassium hydroxide. The structure of the new compound 3 was determined by elemental analysis, IR and NMR techniques. The ¹H and ¹³C NMR signals of the two isomers (trans and cis) of compound 3 were assigned using 2D NMR techniques. The corresponding coupling constants and the tautomeric ratios of isomers were calculated. The ratio of the dominant trans isomer was 64.5%, while the cis isomer was 35.5%.

Key words: NMR, structure analysis, tautomerism, benzimidazole, 1,3,4-oxadiazole

CLC Number:

O482.53

ZHANG Zhi-Guang,JIN Kun, LI Li-Na, LI Ying-Jun. An NMR Study of A Novel 1,3,4-Oxadiazole Derivative Containing Benzimidazole Moiety[J]. Chinese Journal of Magnetic Resonance, 2012, 29(4): 590-597.

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