1-苯基磺酰基吡咯在医药和农药领域有应用,具体用途需参考相关文献。
医药; 农药
合成路线 1(1. 合成:16851-82-4)
产率:87%
合成条件:With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 20℃; for 3 h;
实验步骤:在15分钟内将苯磺酰氯(1.92mL,15.0mmol)的甲苯(15.0mL)溶液加入到吡咯(0.69mL,10.0mmol),硫酸氢四丁基铵(0.34g,1.0mmol)的混合物中,并且 50%氢氧化钠水溶液(10.0mL)的甲苯溶液(30.0mL)。 将混合物在室温下搅拌,并通过薄层色谱监测反应。 在室温下搅拌3小时后,TLC显示反应完成。 分离各层,有机层用水和盐水洗涤,用Na 2 SO 4干燥,过滤并浓缩。 通过快速柱色谱法(硅胶,30%CH 2 Cl 2 /己烷)纯化粗产物,得到1.81g(87%)白色固体。 M. p。 86-87 C; 1 H NMR(300MHz,CDCl 3)δ6.30(m,2H),7.17(m,2H),7.50(m,2H),7.57(m,1H),7.84(m,1H),7.87(m,1H)。
参考文献:
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合成路线 2(3. 合成:16851-82-4)
产率:426 mg
合成条件:With manganese(IV) oxide In dichloromethane at 40℃; for 18 h;
实验步骤:在氮气氛下,将N,N-二烯丙基苯磺酰胺2221(660mg,2.78mmol,1当量)溶解在DCM(30mL)中。加入Grubbs催化剂1(69.5mg,0.084mmol,3.0mol%)并将反应在室温下搅拌3小时。然后将MnO 2(6.09g,70.0mmol,25当量)加入到反应烧瓶中并在搅拌下加热回流18小时。冷却后,将反应内容物通过Celite过滤并用DCM(2×20mL)洗涤。减压浓缩滤液,通过快速柱色谱(c-Hex-EtOAc; 6:1)纯化,得到26(426mg,74%),为浅黄色固体。 Mp = 86-88℃(点亮25mp = 87-88℃); Rf = 0.50(c-Hex-EtOAc; 6:1); 1H NMR(400MHz,CDCl3)7.87-7.84(2H,m,CH)7.61-7.57(1H,m,CH),7.52-7.48(2H,m,CH),7.17-7.16(2H,m,CH) ,6.31-629(2H,m,CH),ppm; 13C NMR(100MHz,CDCl3)139.1,133.7,129.3,126.7,120.8,113.6ppm;。发现(计算值)C10H9NO2S:C,57.76%(57.95%); H,4.07%(4.38%); N,6.91%(6.76%)。
参考文献:
- [1] Tetrahedron, 2016, vol. 72, # 20, p. 2552 - 2559