CN104072406A - 一种合成吡啶及喹啉衍生物的方法 - Google Patents
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Abstract
本发明公开了一种吡啶及喹啉衍生物的合成方法,包括如下步骤:将吡啶或喹啉类化合物A与醛类化合物B在离子液体[Bmim]BF4中加热反应,离子液体[Hnhm]HSO4做催化剂,反应一定时间得到吡啶及喹啉类衍生物C。此反应使用的催化剂[Hmim]H2PO4及溶剂[Bmim]BF4可以回收利用八次并且最终产物的产率没有明显降低。所以,此方法可以极大的降低试验成本,减少环境污染,具有很好的应用前景。
Description
技术领域
本发明涉及一种吡啶及喹啉衍生物的合成方法,属于有机合成领域。
背景技术
吡啶及喹啉衍生物是很常见的杂环化合物,在生物活性分子及药物分子中广泛存在。目前,通过吡啶及喹啉与醛的加成反应来合成吡啶及喹啉衍生物的方法只有少数文献报道(Rao, N. N.; Meshram, H. M. Tetrahedron Lett. 2013, 54, 5087; Jin, J.-J.; Niu, H.-Y.; Qu, G.-R.; Guo H. M.; Fossey, J. S. RSC Adv. 2012, 2, 5968; Wang, F.-F.; Luo, C.-P.; Wang, Y.; Deng, G.; Yang, L. Org. Biomol. Chem. 2012, 10, 8605.)。从已经报道的文献来看,此类反应的的产率还不是很理想,并且底物有局限性,试验成本较高,限制了其大规模的应用。因此,新的更加廉价、环境友好的合成此类化合物的方法还有待开发。
发明内容
本发明的目的在于提供一种廉价、环境友好的合成吡啶及喹啉衍生物的方法。。
本发明提供的吡啶及喹啉衍生物的合成方法,包括如下步骤:将吡啶或喹啉类化合物A与醛类化合物B在离子液体[Bmim]BF4中加热反应,离子液体[Hnhm]HSO4做催化剂,反应一定时间得到吡啶及喹啉类衍生物。
上述制备方法中,吡啶或喹啉类化合物A与醛类化合物B的摩尔比为1:1—3:1。
取代基R1和R2表示连接在苯环上的0,1或2个取代基。取代基R1 和R2各自独立的选自硝基,烷基,氰基和卤原子。
本发明方法具有如下优点:使用的催化剂[Hnhm]HSO4及溶剂[Bmim]BF4可以回收利用8次而产率没有明显降低;此方法可以极大的降低试验成本,减少环境污染,具有很高的应用价值。
具体实施方式:
实施例1、化合物C1的合成
向20ml的反应器中依次加入溶剂[Bmim]BF4(2 ml),2,6-二甲基吡啶(1 mmol),对硝基苯甲醛(0.5 mol),催化剂[Hnhm]HSO4(0.5 mmol),密封反应器,100℃反应24小时。反应体系冷却后,用乙醚(2 ml)萃取6次,合并有机相,有机相用无水硫酸镁干燥,旋转蒸发有机相得到粗产品。粗产品用石油醚:乙酸乙酯=3:1(v/v)为洗脱剂,硅胶为吸附相柱层析分离,得到固体产物C1,产率81%。
由于反应所使用的催化剂及溶剂可以循环利用,萃取后的体系在40摄氏度条件下真空干燥一小时,然后依次加入2,6-二甲基吡啶(1 mmol),对硝基苯甲醛(0.5 mol),密封加热(100℃)24小时,分离得到产物C1,产率为81%。依次类推,催化剂循环利用8次后仍然能到的产率为78%的产物C1,产率没有明显降低,说明此反应的催化剂可以循环利用,极大的降低了实验成本,减少了废弃物的排放和对环境的污染。
核磁共振数据:1H NMR (300 MHz, CDCl3, TMS) δ 8.18 (s, 1H), 8.16 (s, 1H), 7.57 (d, J=5.7 Hz, 2H), 7.50 (t, J=8.0 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 6.87 (d, J=8.0 Hz, 1H), 5.22 (d, J=4.8 Hz, 1H), 3.11-2.98 (m, 2H), 2.54 (s, 3H); 13C NMR (300 MHz, CDCl3, TMS) δ 158.2, 157.7, 151.7, 147.1, 137.5, 126.6, 123.6, 121.7, 120.7, 72.6, 44.5, 24.3;
证明所合成的化合物正确。
实施例2、化合物C2的合成
向20ml的反应器中依次加入溶剂[Bmim]BF4(2 ml),2,6-二甲基吡啶(1 mmol),间氰基苯甲醛(0.5 mol),催化剂[Hnhm]HSO4(0.5 mmol),密封反应器,100℃反应48小时。反应体系冷却后,用乙醚(2 ml)萃取6次,合并有机相,有机相用无水硫酸镁干燥,旋转蒸发有机相得到粗产品。粗产品用石油醚:乙酸乙酯=3:1(v/v)为洗脱剂,硅胶为吸附相柱层析分离,得到固体产物C2,产率80%。
由于反应所使用的催化剂及溶剂可以循环利用,萃取后的体系在40摄氏度条件下真空干燥一小时,然后依次加入2,6-二甲基吡啶(1 mmol),间氰基苯甲醛(0.5 mol),密封加热48小时,分离得到产物C2,产率为81%。依次类推,催化剂循环利用8次后仍然能到的产率为80%的产物C2,产率没有明显降低,说明此反应的催化剂可以循环利用,极大的降低了实验成本,减少了废弃物的排放和对环境的污染。
核磁共振数据:1H NMR (400 MHz, CDCl3, TMS) δ 7.60 -7.47 (m, 5H), 7.03 (d, J=7.6 Hz, 1H), 6.86 (d, J=7.6 Hz, 1H), 5.16 (dd, J=3.2, 8.8 Hz, 1H), 2.96-3.08 (m, 2H), 2.53 (s, 3H); 13C NMR (400 MHz, CDCl3, TMS) δ158.8, 157.5, 149.7, 137.5, 132.2, 126.6, 121.7, 120.7, 119.0, 110.9, 72.7, 44.6, 24.3
证明所合成的化合物正确。
实施例3、化合物C3的合成
向20ml的反应器中依次加入溶剂[Bmim]BF4(2 ml),2-甲基喹啉(1 mmol),间硝基苯甲醛(0.5 mol),催化剂[Hnhm]HSO4(0.5 mmol),密封反应器,100℃反应48小时。反应体系冷却后,用乙醚(2 ml)萃取6次,合并有机相,有机相用无水硫酸镁干燥,旋转蒸发有机相得到粗产品。粗产品用石油醚:乙酸乙酯=3:1(v/v)为洗脱剂,硅胶为吸附相柱层析分离,得到固体产物C3,产率75%。
由于反应所使用的催化剂及溶剂可以循环利用,萃取后的体系在40摄氏度条件下真空干燥一小时,然后依次加入2-甲基喹啉(1 mmol),间硝基苯甲醛(0.5 mol),密封加热48小时,分离得到产物C3,产率为74%。依次类推,催化剂循环利用8次后仍然能到的产率为75%的产物C3,产率没有明显降低,说明此反应的催化剂可以循环利用,极大的降低了实验成本,减少了废弃物的排放和对环境的污染。
核磁共振数据:1H NMR (400 MHz, CDCl3): δ 8.36 (s, 1H), 8.06-8.14 (m, 3H), 7.82 (t, J = 8.6 Hz, 2H), 7.75 (t, J = 7.6 Hz, 1H), 7.57-7.50 (m, 2H), 7.23 (d, J = 2.4 Hz, 1H), 5.42 (dd, J=8.8 Hz, 1H), 3.37-3.27 (m, 2H); 13C NMR (400 MHz, CDCl3): δ 159.7, 148.4, 146.2, 137.4, 132.1, 130.2, 129.4,128.6, 127.0, 127.0, 126.6, 122.4, 122.0, 121.1, 72.1, 45.3;
证明所合成的化合物正确。
实施例4、化合物C4的合成
向20ml的反应器中依次加入溶剂[Bmim]BF4(2 ml),2-甲基-6-溴喹啉(1 mmol),对硝基苯甲醛(0.5 mol),催化剂[Hnhm]HSO4(0.5 mmol),密封反应器,100℃反应24小时。反应体系冷却后,用乙醚(2 ml)萃取6次,合并有机相,有机相用无水硫酸镁干燥,旋转蒸发有机相得到粗产品。粗产品用石油醚:乙酸乙酯=3:1(v/v)为洗脱剂,硅胶为吸附相柱层析分离,得到固体产物C4,产率69%。
由于反应所使用的催化剂及溶剂可以循环利用,萃取后的体系在40摄氏度条件下真空干燥一小时,然后依次加入2-甲基-6-溴喹啉(1 mmol),对硝基苯甲醛(0.5 mol),1,4-二氧六环(1 ml),密封加热24小时,分离得到产物C4,产率为67%。依次类推,催化剂循环利用8次后仍然能到的产率为68%的产物C4,产率没有明显降低,说明此反应的催化剂可以循环利用,极大的降低了实验成本,减少了废弃物的排放和对环境的污染。
核磁共振数据:1H NMR (300 MHz, CDCl3, TMS) δ 8.19 (d, J=8.2 Hz, 2H), 8.01 (d, J=8.3 Hz, 1H), 7.95 (d, J=8.2 Hz, 1H), 7.91 (d, J=8.9 Hz, 1H), 7.78 (dd, J=8.6, 1.6 Hz, 1H), 7.62 (d, J=8.5 Hz, 2H), 7.22 (d, J=8.6 Hz, 1H), 6.33 (s, 1H), 5.42 (dd, J=8.2 Hz, 1H), 3.34-3.21 (m, 2H); 13C NMR (300 MHz, CDCl3, TMS) δ 160.2, 151.2, 147.3, 145.6, 136.2, 133.6, 130.4, 129.8, 128.1, 126.7, 123.8, 122.9, 120.5, 72.1, 45.5;
证明所合成的化合物正确。
实施例5、化合物C5的合成
向20ml的反应器中依次加入溶剂[Bmim]BF4(2 ml),2-甲基喹喔啉(1 mmol),对硝基苯甲醛(0.5 mol),催化剂[Hnhm]HSO4(0.5 mmol),密封反应器,110℃反应24小时。反应体系冷却后,用乙醚(2 ml)萃取6次,合并有机相,有机相用无水硫酸镁干燥,旋转蒸发有机相得到粗产品。粗产品用石油醚:乙酸乙酯=3:1(v/v)为洗脱剂,硅胶为吸附相柱层析分离,得到固体产物C5,产率87%。
由于反应所使用的催化剂及溶剂可以循环利用,萃取后的体系在40摄氏度条件下真空干燥一小时,然后依次加入2-甲基喹喔啉(1 mmol),对硝基苯甲醛(0.5 mol),密封加热24小时,分离得到产物C5,产率为85%。依次类推,催化剂循环利用8次后仍然能到的产率为86%的产物C5,产率没有明显降低,说明此反应的催化剂可以循环利用,极大的降低了实验成本,减少了废弃物的排放和对环境的污染。
核磁共振数据:1H NMR (400 MHz, CDCl3): δ 8.71 (s, 1H), 8.23 (d, J = 8.6 Hz, 2H), 8.10-8.06 (m, 2H), 7.83-7.78 (m, 2H), 7.66 (d, J = 8.6 Hz, 2H), 5.48 (dd, J = 2.8 Hz, J = 8.8 Hz, 1H), 3.45-3.32 (m, 2H); 13C NMR (400 MHz, CDCl3): δ154.1, 150.6, 147.4, 145.9, 141.7, 141.1, 130.8, 129.9, 128.6, 126.7, 123.9, 71.9, 43.3;
证明所合成的化合物正确。
实施例6、化合物C6的合成
向20ml的反应器中依次加溶剂[Bmim]BF4(2 ml),2,5-二甲基吡嗪(1 mmol),对硝基苯甲醛(0.5 mol),催化剂[Hnhm]HSO4(0.5 mmol),密封反应器,100℃反应48小时。反应体系冷却后,用乙醚(2 ml)萃取6次,合并有机相,有机相用无水硫酸镁干燥,旋转蒸发有机相得到粗产品。粗产品用石油醚:乙酸乙酯=3:1(v/v)为洗脱剂,硅胶为吸附相柱层析分离,得到固体产物C6,产率75%。
由于反应所使用的催化剂及溶剂可以循环利用,萃取后的体系在40摄氏度条件下真空干燥一小时,然后依次加入2,5-二甲基吡嗪(1 mmol),对硝基苯甲醛(0.5 mol),密封加热48小时,分离得到产物C6,产率为74%。依次类推,催化剂循环利用8次后仍然能到的产率为75%的产物C6,产率没有明显降低,说明此反应的催化剂可以循环利用,极大的降低了实验成本,减少了废弃物的排放和对环境的污染。
核磁共振数据:mp 135-137 0C; IR(KBr) ν 1597, 1519, 1421, 1346, 860, 831 cm-1;1H NMR (300 MHz, DMSO-d6, TMS) δ 8.33 (s, 1H), 8.26 (s, 1H), 8.16 (d, J=8.7 Hz, 2H), 7.59 (d, J=8.7 Hz, 2H), 5.13-5.07 (m, 2H), 3.03-3.00 (m, 2H), 2.43 (s, 3H);13C NMR (300 MHz, DMSO-d6, TMS) δ 153.6, 153.3, 153.1, 147.0, 142.7, 142.4, 127.6, 123.8, 71.7, 44.9, 21.5. HRMS (ESI) calculated for C13H13N3O3: 260.0990 (M+H)+, Found: 260.1029.
证明所合成的化合物正确。
实施例7、化合物C7的合成
向20ml的反应器中依次加入溶剂[Bmim]BF4(2 ml),2,4,6-三甲基吡啶(1 mmol),对硝基苯甲醛(0.5 mol),催化剂[Hnhm]HSO4(0.5 mmol),密封反应器,100℃反应48小时。反应体系冷却后,用乙醚(2 ml)萃取6次,合并有机相,有机相用无水硫酸镁干燥,旋转蒸发有机相得到粗产品。粗产品用石油醚:乙酸乙酯=3:1(v/v)为洗脱剂,硅胶为吸附相柱层析分离,得到固体产物C7,产率82%。
由于反应所使用的催化剂及溶剂可以循环利用,萃取后的体系在40摄氏度条件下真空干燥一小时,然后依次加入2,4,6-三甲基吡啶(1 mmol),对硝基苯甲醛(0.5 mol),密封加热48小时,分离得到产物C7,产率为82%。依次类推,催化剂循环利用8次后仍然能到的产率为80%的产物C7,产率没有明显降低,说明此反应的催化剂可以循环利用,极大的降低了实验成本,减少了废弃物的排放和对环境的污染。
核磁共振数据:1H NMR (300 MHz, CDCl3, TMS) δ 8.17 (d, J=8.7, 2H), 7.57 (d, J=8.4 Hz, 2H), 6.88 (s, 1H), 6.72 (s, 1H), 5.20 (dd, J=3.0, 8.4 Hz, 1H), 3.08-2.93 (m, 2H), 2.50 (s, 3H), 2.26 (s, 3H); 13C NMR (300 MHz, CDCl3, TMS) δ 157.9, 157.1, 151.9, 148.8, 147.1, 126.6, 123.6, 122.7, 121.7, 72.7, 44.4, 24.1, 21.0;
证明所合成的化合物正确。
Claims (3)
1.一种合成吡啶及喹啉衍生物的方法,包括如下步骤:将吡啶或喹啉类化合物A与醛类化合物B在离子液体[Bmim]BF4中加热反应,离子液体[Hnhm]HSO4做催化剂,反应一定时间得到吡啶及喹啉类衍生物,并且此反应使用的离子液体[Bmim]BF4和催化剂[Hnhm]HSO4可以回收利用八次而产率没有明显降低。
2.根据权利要求1所述的方法,其特征在于此反应使用的催化剂[Hnhm]HSO4为。
3.根据权利要求1所述的方法,其特征在于此反应使用离子液体 [Bmim]BF4为溶剂,离子液体 [Bmim]BF4为。
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