含苯并咪唑环的1, 3, 4-噁二唑衍生物的核磁共振研究

波谱学杂志 ›› 2012, Vol. 29 ›› Issue (4): 590-597.

含苯并咪唑环的1, 3, 4-噁二唑衍生物的核磁共振研究

张治广¹，靳焜²，李丽娜¹，李英俊^1*

1. 辽宁师范大学化学化工学院，辽宁大连 116029； 2. 大连理工大学精细化工国家重点实验室，辽宁大连 116023

收稿日期:2012-03-26 修回日期:2012-04-13 出版日期:2012-12-05 发布日期:2012-12-05
基金资助:
辽宁省自然科学基金资助项目(20102126).

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

ZHANG Zhi-Guang¹, JIN Kun², LI Li-Na¹, LI Ying-Jun^1*

1. College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China;
2. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, China

Received:2012-03-26 Revised:2012-04-13 Online:2012-12-05 Published:2012-12-05
Supported by:
辽宁省自然科学基金资助项目(20102126).

摘要/Abstract

摘要：

在无水乙醇和KOH 存在下，将2-苯氧甲基苯并咪唑-1-乙酰肼(1)与CS₂反应，合成出了中间体5-(2-苯氧甲基苯并咪唑-1-亚甲基)-2-巯基-1,3,4-噁二唑(2)，此中间体再与氯乙酰苯胺反应，得到一种新化合物-N-苯基-2-[5-(2-苯氧甲基苯并咪唑-1-亚甲基)-1,3,4-噁二唑-2-硫基]乙酰胺(3). 采用元素分析、IR及NMR技术确定了新化合物3的结构，并利用2D NMR技术对其trans和cis两种异构体的¹H和¹³C NMR谱带进行了全归属，给出了相应的偶合常数J值以及异构体所占的比例. 实验表明，新化合物3在DMSO中存在着trans和cis两种异构体的互变，并且trans异构体占主导，含量为64.5%，而cis异构体的含量为35.5%.

关键词: 核磁共振(NMR), 结构解析, 互变异构, 苯并咪唑, 1,3,4-噁二唑

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

中图分类号:

O482.53

张治广, 靳焜, 李丽娜, 李英俊. 含苯并咪唑环的1, 3, 4-噁二唑衍生物的核磁共振研究[J]. 波谱学杂志, 2012, 29(4): 590-597.

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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