【作者】 高晶晶；

【导师】 王敏；

【作者基本信息】 渤海大学 ， 应用化学， 2012， 硕士

【摘要】 2,4,5-三取代咪唑、2-取代-2,3-二氢-4(1H)-喹唑啉酮及1-氨甲酸酯基-烷基-2-萘酚衍生物具有显著的生物活性和药理活性，是重要的药物合成中间体，在农药和医药领域有着广泛的应用。本文主要分为三部分，采用不同的绿色工艺合成了2,4,5-三取代咪唑、2-取代-2,3-二氢-4(1H)-喹唑啉酮及1-氨甲酸酯基-烷基-2-萘酚衍生物。第一部分是在无催化剂、乙醇为溶剂、加热回流条件下，以苯偶酰、芳香醛、醋酸铵为原料，三组分“一锅法”合成了十五种2,4,5-三取代咪唑衍生物。实验得出的较佳反应条件是：原料摩尔比为1:1:6，乙醇10mL。醋酸铵过量起到“反应自身催化”的作用，产品产率65-98%。第二部分是在甲基磺酸亚铈催化作用下，以水为溶剂，将2-氨基苯甲酰胺和醛/酮室温研磨后，置于60oC加热反应（苯甲醛除外），可有效环化合成一系列2-取代-2,3-二氢-4(1H)-喹唑啉酮衍生物。实验得出较佳反应条件是：原料摩尔比为1:1，催化剂用量为1mol%（以2-氨基苯甲酰胺的摩尔数计），水1mL。产品的产率为84-94%。催化剂连续使用五次后催化效果仍较好。第三部分是在无溶剂，以甲基磺酸铜为催化剂条件下，将2-萘酚、醛、氨基甲酸酯三组分“一锅法”反应，合成了十八种1-氨甲酸酯基-烷基-2-萘酚衍生物。实验得出的较佳反应条件是：原料摩尔比为1:1:1.2，温度为70oC，催化剂用量为2mol%（以2-萘酚的摩尔数计）。产品的产率为65-92%，催化剂连续使用五次后催化效果仍较好。所合成的化合物分别用IR、1H-NMR、质谱及元素分析进行表征。更多还原

【Abstract】 2,4,5-Trisubstituted imidazoles,2-substituted-2,3-dihydro-4(1H)-quinazolinones and1-carbamato-alkyl-2-naphthols derivatives possess distinct pharmaceutical and biologicalactivities. They are important intermediates in medicinal synthesis and they are appliedwidely in the field of agrochemicals and drugs. The thesis consists of three parts including thegreen sysnthesis of2,4,5-trisubstituted imidazoles,2-substituted-2,3-dihydro-4(1H)-quinazolinones and1-carbamato-alkyl-2-naphthols derivatives.In the first part, the2,4,5-trisubstituted imidazoles were synthesized by athree-component, one-pot condensation of benzil, aldehydes and ammonium acetate inrefluxing ethanol without adding catalyst. The optimum operation conditions were as follows:the molar ratio of benzil, aldehydes and ammonium acetate is1:1:6and ethanol is10mL.The excess amount of NH4OAc would promote the reaction by the ‘‘catalyzed-by-itself’’. Theyields of products are65-98%.In the second part, a series of2-substituted-2,3-dihydro-4(1H)-quinazolinones weresynthesized efficiently through cyclocondensation of2-anthranilamide with aldehydes orketones (except benzaldehyde) in the presence of a recyclable cerous methanesulfonate at60oC after grinding at room temperature under aqueous conditions. The optimum operationconditions were follows: the molar ratio of2-anthranilamide to aldehydes or ketones is1:1,the amount of catalyst is0.01mmol (based on the mole of2-anthranilamide), and water is1mL. The yields of products are84-94%. The catalytic activity of the catalyst is preferableafter five consecutive reactions.In the third part, the1-carbamato-alkyl-2-naphthols were synthesized by a one-potthree-component condensation of2-naphthol, aldehydes and carbamate in the presence of arecyclable copper methanesulfonate without solvent. The optimum operation conditions wereas follows: the molar ratio of2-naphthol, aldehydes and carbamate is1:1:1.2, the amount ofcatalyst is0.02mmol (based on the mole of2-naphthol), the temperature at70oC. The yieldsof products are65-92%. The catalytic activity of the catalyst is preferable after fiveconsecutive reactions.The structures of products were characterized by IR,1H-NMR, MS and elemental analysis.更多还原