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Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (07): 874-879. Previous Articles     Next Articles

Reports

超声辐射下合成4,5-二氢-1-取代胺亚甲基-3-(2-三氟甲基苯并[d]咪唑- 1-亚甲基)-4-芳基-1,2,4-三唑-5-硫酮

时天昊，李燕萍，刘晨江*   

  1. (新疆大学化学化工学院 石油天然气精细化工教育部重点实验室 乌鲁木齐 830046)
  • 收稿日期:2006-06-26 修回日期:1900-01-01 发布日期:2007-06-30
  • 通讯作者: 刘晨江*

Synthesis of 4,5-Dihydro-1-substituted Aminomethyl-3- (2-trifluoromethylbenzo[d]imidazol-1-ylmethyl)-4-aryl-1,2,4-triazole-5-thione under Ultrasonic Radiation

SHI Tian-Hao,LI Yan-Ping,LIU Chen-Jiang*   

  1. (Key Laboratory of Oil and Gas Fine Chemicals of Ministry of Education, College of Chemistry and
    Chemical Engineering, Xinjiang University, Ulumqi 830046)
  • Received:2006-06-26 Revised:1900-01-01 Published:2007-06-30
  • Contact: LIU Chen-Jiang*

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863

The reaction of 1-hydrazinocarbonylmethyl-2-trifluoromethylbenzo[d]imidazole (1) with aryl isothiocyanate gave 4-acylthiosemicarbazides 2a～2d in the presence of anhydrous ethanol. Then compounds 2a～2d were cyclized in aqueous sodium hydroxide to afford 4,5-dihydro-3-(2-trifluoromethyl- benzo[d]imidazole-1-ylmethyl)-4-aryl-1,2,4-triazole-5-thiones (3a～3d). And resulting compounds 3a～3d were treated with four amines to obtain sixteen new Mannich bases 4a～4d, 5a～5d, 6a～6d and 7a～7d by means of ultrasonic radiation method and ordinary method. Compared with ordinary method, ultrasonic radiation method consistently had many merits with simple operation, short time, mild reaction conditions, excellent yields and less secondary reactions, which afforded an effective method to synthesize Mannich base. The structures of the products were confirmed by elemental analysis, IR and 1H NMR spectra.

Key words: Mannich base, 2-trifluoromethylbenzo[d]imidazole, synthesis, 1,2,4-triazole, ultrasonic radiation