离子液体体系中氮杂环化合物的合成研究
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摘要
氮杂环化合物是一类重要的杂环化合物,在功能材料、医药、农药和生物等领域有着广泛的应用,开展对氮杂环化合物的合成研究具有重要的意义。传统的化学合成方法由于在化学反应和分离过程中使用了大量有毒有害、易挥发的有机溶剂,造成了对环境的严重污染。离子液体是一种新型的绿色溶剂,是绿色化学的研究热点之一。功能化离子液体的发展,使离子液体不但可以作为溶剂,而且可以作为催化剂在有机合成中发挥着越来越多的作用。本论文基于绿色化学的发展要求,研究了离子液体体系中氮杂环化合物的合成。
     论文考察了咪唑型、己内酰胺型、季铵盐型等几种离子液体在3,7-二硝基-1,3,5,7-四氮杂双环[3.3.1]壬烷(DPT)的合成中的应用,结果表明季铵盐型离子液体[TMPSA][HSO4]的效果最好;当[TMPSA][HSO4]用量为脲的10mol%时,优化的反应条件下,DPT的产率达70%。研究了含Br(?)nsted酸性官能团的季铵盐型离子液体在2,5,7,9-四硝基-2,5,7,9-四氮杂双环[4.3.0]壬酮-8(K-56)的合成中的应用,取得了较好的效果;离子液体体系下,高产率地析出了前体化合物2,5,7,9-四氮杂双环[4.3.0]壬酮-8的二盐酸盐一水合物,在对前体化合物硝化之后,得到目标产物K-56,总得率为57%(以脲计)。
     研究了离子液体3-(N,N-二甲基-N-十二烷基铵基)丙磺酸的硫酸氢盐([DDPA][HSO4])在水相中催化芳香醛、二羰基化合物、脲的三组分Biginelli反应,合成了一系列的3,4-二氢嘧啶-2-酮衍生物;苯甲醛、乙酰乙酸甲酯、脲在90℃反应20min,相应产物的产率为91%;产物与催化剂通过简单的过滤即可分离,离子液体不经处理即可循环使用。将离子液体N,N,N’,N’-四甲基-N,N’-二磺酸丙基乙二铵二硫酸氢盐([TMEDAPS][HSO4])在水相中催化1,2-二酮和1,2-苯二胺衍生物的缩合反应,从而合成相应的喹喔啉衍生物,产率84-95%;[TMEDAPS][HSO4]含有两个Br(?)nsted酸性官能团,且具有季铵盐相转移催化剂的结构,催化性能很好,可重复使用且没有明显的催化活性的降低。
     在PEG1000-DAIL/甲苯温控体系中合成四氢-p-咔啉类化合物,相应的产物产率为88-93%。结果表明,PEG1000-DAIL/甲苯温控体系不仅具有优良的催化性能,且催化剂与产物采用分液方法分离,操作简单,经循环使用且没有明显的催化活性的降低。
     采用[DDPA][HSO4]在超声波促进下催化胺与2,5-己二酮的Paal-Knorr反应,从而合成相应的吡咯衍生物,产率78-95%;反应时间大大缩短(如苯胺与2,5-己二酮的反应时间由40min缩短为5min),产率较高,操作方便,后处理简单,离子液体可循环使用,具有一定的实用价值。采用离子液体1-丁基-3-甲基咪唑磷酸二氢盐([BMIm][H2PO4])在微波辐射下催化醛、1,2-二酮化合物和醋酸铵的三组分反应,从而合成相应的2,4,5-三取代咪唑衍生物,产率86~96%;微波辐射下,[BMIm][H2PO4]能较好地催化合成2,4,5-三取代咪唑衍生物,反应在数分钟内完成,产率较高,操作方便,[BMIm][H2PO4]循环使用且没有明显的催化活性的降低。
Nitrogen-containing heterocyclic compounds are an important class of heterocycles and applied in many areas, such as functional materials, medicine, pesticide and biological fields, so study on the synthesis of them is of great significance. The traditional methods of synthesis caused serious environmental pollution because of using a great deal of toxic and harmful, volatile organic solvents in the processes of reaction and separation. Ionic liquids, considered as novel solvents, have become a hot area of green chemistry. Functionalized ionic liquids have marched far beyond solvents, showing their significant role in organic synthesis as catalysts. In this paper, the synthesis of nitrogen-containing heterocyclic compounds in ionic liquid systems was investigated based on requirements of the development of green chemistry.
     Firstly, applications of several ionic liquids that bear group in imidazolium cation, caprolactam cation, or acyclic tri-alkanyl-ammonium cation in the synthesis of 3,7-dinitro-1,3,5,7-tetraazabicyclo[3.3.1]nonane (DPT) were invested and the results showed that the quaternary ammonium salt-type ionic liquid [TMPSA][HSO4] was the best one. In the presence of 10 mol%of [TMPSA][HSO4] (based on urea), the yield of DPT was obtained with 70% under the optimum conditions. Next, a facile and efficient method for the synthesis of 2,5,7,9-tetranitro- 2,5,7,9-tetraazabicyclo[4.3.0]nonane-8-one has been developed in this paper. In the procedure, the precursor compound 2,5,7,9-tetrahydro-2,5,7,9-tetraazabicyclo [4.3.0]nonane-8-one dihydrochloride was prepared in high yield catalyzed by task-specific Br(?)nsted- acidic ionic liquids that bear group in acyclic tri-alkanyl-ammonium cation and the subsequent nitration of the precursor compound gave the desired product (yield 57% based on urea).
     Secondly, a functionalized ionic liquid,3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulfate ([DDPA][HSO4]) has been found to be an effective catalyst for assembling 3,4-dihydropyrimidine-2-(1H)-ones via three-component Biginelli reaction in water. The yield of corresponding product was 91% when the Biginelli reaction of benzaldehyde, methyl acetoacetate, urea was selected as model in 20 min at 90℃. The products could be separated by simple filtration and the catalyst could be recycled up to next time without any treatment. Subsequently, N,N,N',N'-Tetramethyl-N,N'-bis(3-sulfopropyl)-ethylenediammonium bis(hydrogensulfate) ([TMEDAPS][HSO4]) catalyzed condensation reaction of 1,2-ketone and 1,2-diaminobenzene derivative proceeded rapidly to afford corresponding quinoxaline derivatives with 84~95% yields in water. [TMEDAPS][HSO4] bears two Br(?)nsted-acidic functional groups and has the structure of quaternary ammonium salt as phase transfer catalyst. The catalyst was active in the reaction and could be reused without obviously decreasing the catalytic activity.
     Furthermore, applications of PEG1000-DAIL/toluene thermoergulated system in the synthesis of tetrahydro-β-carboline derivatives were invested and good results were obtained with 88~93% yields. The catalyst could be easily separated from products by decantation and recycled without obviously decreasing the catalytic activity.
     Lastly, corresponding pyrrole derivatives with 78~95% yields were synthesized via ultrasonic-assisted Paal-Knorr condensation of amine and 2,5-hexanedione using [DDPA][HSO4] as catalyst. The reaction time of aniline and 2,5-hexanedione was shortened from 40min to 5min. The method showed certain practical value for high yield, shorter reaction time, and simple procedure. The ionic liquid could be recycled without obviously decreasing the catalytic activity. Then 1-butyl-3-methylimidazolium dihydrogen phosphate ([BMIm][H2PO4]) catalyzed three-component reaction of aldehyde,1,2-diketones and ammonium acetate under microwave irradiation to afford corresponding 2,4,5-trisubstituted imidazole derivatives with 86~96% yields. The attractive features of this protocol are short reaction time (only a few minutes), high yields, and the easy workup procedure. [BMIm][H2PO4] could be recycled without obviously decreasing the catalytic activity.
引文
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