轴手性多活性中心BINOL酰胺的合成及催化Hantzsch反应
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摘要
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.
The Hantzsch reaction of an environmentally friendly,axis chiral multiple BINOL amides catalyzing of aromatic aldehydes,acetacetic ester and ammonium bicarbonate has been developed. The results demonstrated that the Hantzsch reaction of aromatic aldehydes,acetacetic ester and ammonium bicarbonate was efficiently performed,Hantzsch ester formation was increased in reflux CH_2Cl_2 with axis chiral multiple BINOL amides(0. 075 mmol). The product was characterized by IR,NMR,melting point. Compared with the conventional synthesis method,ultrasonic method is simple,high yield,rapid and potential.
The Hantzsch reaction of an environmentally friendly,axis chiral multiple BINOL amides catalyzing of aromatic aldehydes,acetacetic ester and ammonium bicarbonate has been developed. The results demonstrated that the Hantzsch reaction of aromatic aldehydes,acetacetic ester and ammonium bicarbonate was efficiently performed,Hantzsch ester formation was increased in reflux CH_2Cl_2 with axis chiral multiple BINOL amides(0. 075 mmol). The product was characterized by IR,NMR,melting point. Compared with the conventional synthesis method,ultrasonic method is simple,high yield,rapid and potential.
引文
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[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.