5-（2-噻吩）-2-对-甲苯基噁唑的合成

Synthesis of 5-(thiophen-2-yl)-2-p-tolyloxazole

摘要:

以2-溴-1-（2-噻吩）-1-乙酮和对-甲基苯甲胺为原料，在复合催化剂碘与叔丁基过氧化氢的作用下，通过氧化环合反应合成了5-（2-噻吩）-2-对-甲苯基噁唑。产物结构经FTIR，NMR 和MS检测。结果显示：合成产物的最佳条件为：2-溴-1-（2-噻吩）-1-乙酮1 mmol、对-甲基苯甲胺1.3 mmol、碘0.2 mmol、质量分数55%的叔丁基过氧化氢1.2mmol、碳酸氢钠1.0 mmol，室温下反应12 h，产物收率为89.7 %。抑菌圈测定结果显示该产物对大肠杆菌具有强的抑菌能力。

Abstract:

5-(thiophen-2-yl)-2-p-tolyloxazole was synthesized via an oxidative cyclization reaction between 2-bromo-1-(thiophen-2-yl)-1-ethanone and p-tolylmethanamine in the presence of a catalyst amount of iodine and tert-butyl hydroperoxide (TBHP). The structure of the targeted product was confirmed by Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR) and mass spectroscopy (MS). The results indicated that the optimum synthetic conditions were determined as follows: the amount of 2-bromo-1-(thiophen-2-yl)-1-ethanone, p-tolylmethanamine, iodine, TBHP (mass fraction 55%) and sodium bicarbonate was 1 mmol, 1.3 mmol, 0.2 mmol, 1.2 mmol and 1.0 mmol, respectively, at room temperature for 12 h. The yield of the product reached 89.7 % under the above synthetic condition. The zone of inhibition showed that this compound exhibited a remarkable antibacterial activity against Escherichia coli.