轴手性多活性中心BINOL酰胺的合成及催化Hantzsch反应Synthesis and Catalytic Hantzsch Reaction of Axis Chiral Multiple BINOL Amides
王金娟;裴学海;杨志翔;王文琛;尹晓刚;陈治明;
摘要(Abstract):
探讨了环境友好和无毒性的轴手性多活性中心的BINOL酰胺催化的芳香醛、乙酰丙酮及碳酸氢铵的Hantzsch反应.研究表明,在回流条件下,CH_2Cl_2中,在0.075 mmol轴手性多活性中心BINOL酰胺存在下,芳香醛、乙酰丙酮及碳酸氢铵能有效进行Hantzsch反应,高产率生成Hantzsch酯.产物通过红外、核磁、熔点进行表征.该方法与现有合成方法相比,具有操作简便、收率高、用时短等优点,有潜在的应用前景.
关键词(KeyWords): BINOL酰胺;合成;Hantzsch反应;Hantzsch酯
基金项目(Foundation): 贵州师范大学研究生创新基金资助项目(研创201621);; 国家自然科学基金资助项目(21362006)
作者(Authors): 王金娟;裴学海;杨志翔;王文琛;尹晓刚;陈治明;
参考文献(References):
- [1]赵炳筠,朱晓晴,何家骐,等.1,4-二氢Hantzsch吡啶衍生物的合成及其1HNMR和荧光光谱研究[J].高等学校化学学报,1999,20(11):1733-1737.
- [2]BOSSERT F,VATER W.Dihydropyridines,a new group of strongly effective coronary therapeutic agents[J].Science of Nature,1971,58(11):578.
- [3]BOSSERT F,MEYER H,WEHINGER E.4-Aryldihydropyridines,a new class of highly active calcium antagonists[J].Angewandte Chemie International Edition,2010,20(9):762-769.
- [4]JIANG Z Q,JI S J,LU J,et al.A mild and efficient synthesis of 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran derivatives in room temperature lonic liquids[J].Chinese Journal of Chemistry,2005,23(8):1085-1089.
- [5]金建忠,闻鸣,沈超,等.水相催化Hantzsch反应[J].应用化学,2015,32(12):1392-1397.
- [6]史达清,牟杰,庄启亚,等.水溶液中4-芳基-1,4-二氢吡啶衍生物的一步合成法[J].有机化学,2004,24(9):1042-1044.
- [7]蔡小华,张国林.无溶剂一锅法合成1,4-二氢吡啶[J].有机化学,2005,25(8):930-933.
- [8]LOEV B,SNADER K M.The Hantzsch reaction.I.Oxidative dealkylation of certain dihydropyridines[J].Journal of Organic Chemistry,1965,30(6):1914-1916.
- [9]SABITHA G,REDDY G S K K,Reddy C S,et al.A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature[J].Cheminform,2003,34(34):4129-4131.
- [10]路军,白银娟,杨秉勤,等.1,4-二氢吡啶衍生物合成方法的改进和芳构化研究[J].有机化学,2000,20(4):514-517.
- [11]王建平,付永举,王建革.具有生物活性的1,4-二氢吡啶衍生物的水热法合成及结构表征[J].化学研究与应用,2007,19(12):1379-1381.
- [12]MIRZAEI H,DAVOODNIA A.Microwave assisted sol-gel synthesis of Mg O nanoparticles and their catalytic activity in the synthesis of Hantzsch 1,4-dihydropyridines[J].Chinese Journal of Catalysis,2012,33(9/10):1502-1507.
- [13]SHAMIM T,GUPTA M,PAUL S.The oxidative aromatization of Hantzsch 1,4-dihydropyridines Bymolecular oxygen using surface functionalized silica supported cobalt catalysts[J].Journal Molecular Catalysis A Chemical,2009,302(1/2):15-19.
- [14]TAJBAKHSH M,ALAEE E,ALINEZHAD H,et al.Titanium dioxide nanoparticles catalyzed synthesis of Hantzsch esters and polyhydroquinoline derivatives[J].Chinese Journal of Catalysis,2012,33(9/10):1517-1522.
- [15]陈翠,谭丽泉,邱会华.乙酰乙酰芳胺类化合物导向的五取代1,4-二氢吡啶衍生物的合成[J].有机化学,2014,34(8):1673-1676.
- [16]王道林,吴健莹,董哲,等.3,3'-芳基(烷基)二(4-氨基香豆素)和1,4-二氢吡啶并[3,2-c][5,6-c]双香豆素类衍生物的有效合成[J].有机化学,2015,35(1):200-206.
- [17]JAVAD S,SAYED H B,SHIVA D K.Cobalt nanoparticles promoted highly efficient one pot four-component synthesis of1,4-dihydropyridines under solvent-free conditions[J].Chinese Journal of Catalysis,2011,32(12):1850-1855.
- [18]PELLISSIER H.Asymmetric organocatalysis[J].Tetrahedron,2007,63(38):9267-9331.
- [19]DONDONI A,MASSI A.Asymmetric organocatalysis:from infancy to adolescence[J].Angewandte Chemie International Edition,2008,47(25):4638-4660.
- [20]易景中,王湧,刘澍,等.一种具有手性联二萘骨架新型TADDOL配体的合成[J].厦门大学学报(自然科学版),2004,43(5):652-656.