离子液体中捕捉氧叶立德的三组分反应研究以及功能杂环化合物的合成研究
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摘要
多组分反应具有简单,高效,高选择性和原子经济性的特点。近年来,我们课题组发现了一类以胺/羟鎓叶立德为中间体的重氮化合物参与的多组分新反应:基于上述的研究基础,我们较为系统研究了以羟鎓叶立德为中间体的重氮多组分反应。
本论文首先以重氮苯基乙酸甲酯、苄醇和对硝基苯甲醛为三组分模板,较为初步地研究了以羟鎓叶立德为中间体的重氮多组分反应在离子液体中的化学行为,同时发现水这种“活泼的醇”在离子液体介质中仍然具有非常出色的化学反应性。就此,我们提出了一种制备α,β-双羟基化合物的绿色高效方法。该方法原料成本价廉易得,同时采用“一锅法”的新合成方法,同时构建两个手性碳,制备路线短,操作简单,反应条件缓和,有较强的应用价值。我们使用离子液体[bmim]PF_6与水构成两相反应介质,回收催化剂并能重复利用多次,使这种新的合成方法更能符合绿色化学的要求。同时,我们还利用ICP方法,分析了重复使用水相和离子液体的过程中,金属催化剂的机械损失率(降解)和反应性的初步规律。
3-乙酰基吡咯-2-甲酸甲酯作为一种吡咯的衍生物,是广泛应用于药物中的一类有用的中间体。本论文中,我们初步摸索了它的全合成方法,从而提出了一条较为实用的合成工艺路线。
(S)-2-羧基环丁胺作为一种重要的药物中间体,它的化学合成方法也得到了较为系统的研究。在其前体的化学合成研究中,我们总结出了一条较为新颖可行的合成路线,相比较现有的文献报道而言,它原料简单,廉价易得,无需手性拆分,因此产业化的前景更佳。
联噻吩甲醛以及呋喃类小分子作为一种非常有用的药物中间体,其合成的工艺也得到较为详尽的研究。
Metal-mediated carbenoid reactions with Diazo Compounds are the most efficient synthetic methods in organic chemistry in the past decades.Recently,our group reported a novel three-component reaction in which oxonium ylides generated in-situ from diazo compounds catalyzed by Rh(Ⅱ) with alcohols underwent nucleophilic addition to aldehydes.
Furthermore,it demonstrated that electron-rich and less hindered alcohols favored the alcoholic oxonium ylide formation and gave the three-component products in good yield.Interestingly,we found that water served as a "active alcohol" which generated oxonium ylide trapped by electron-deficient aryl aldehydes to afford a three-component product in excellent yield.It is worth noting that this approach should be practically applied to efficiently constructα,β-dihydroxyl ester derivatives in[bmim]PF_6 and water biphasic system.The starting materials are cheap and this method is regarded as an available way to effectively constructα,β-dihydroxyl ester derivatives.We reuse this biphasic medium and catalyst for several times for the purpose of green chemistry.Meanwhile,we take advantage of ICP technology to Study the relationship between recycled reaction medium and remained catalyst.
methyl 3-acetyl-1H-pyrrole-2-carboxylate is some sort of compound which is used for medicine.The total synthetic method is thoroughly studied under optimal condition.
(S)-azetidine-2-carboxylic acid precursor is also studied with a relatively new way which is good for chemical processing.
Some sort of dithiophen compound and furan compound are synthesized by optimal method.
本论文首先以重氮苯基乙酸甲酯、苄醇和对硝基苯甲醛为三组分模板,较为初步地研究了以羟鎓叶立德为中间体的重氮多组分反应在离子液体中的化学行为,同时发现水这种“活泼的醇”在离子液体介质中仍然具有非常出色的化学反应性。就此,我们提出了一种制备α,β-双羟基化合物的绿色高效方法。该方法原料成本价廉易得,同时采用“一锅法”的新合成方法,同时构建两个手性碳,制备路线短,操作简单,反应条件缓和,有较强的应用价值。我们使用离子液体[bmim]PF_6与水构成两相反应介质,回收催化剂并能重复利用多次,使这种新的合成方法更能符合绿色化学的要求。同时,我们还利用ICP方法,分析了重复使用水相和离子液体的过程中,金属催化剂的机械损失率(降解)和反应性的初步规律。
3-乙酰基吡咯-2-甲酸甲酯作为一种吡咯的衍生物,是广泛应用于药物中的一类有用的中间体。本论文中,我们初步摸索了它的全合成方法,从而提出了一条较为实用的合成工艺路线。
(S)-2-羧基环丁胺作为一种重要的药物中间体,它的化学合成方法也得到了较为系统的研究。在其前体的化学合成研究中,我们总结出了一条较为新颖可行的合成路线,相比较现有的文献报道而言,它原料简单,廉价易得,无需手性拆分,因此产业化的前景更佳。
联噻吩甲醛以及呋喃类小分子作为一种非常有用的药物中间体,其合成的工艺也得到较为详尽的研究。
Metal-mediated carbenoid reactions with Diazo Compounds are the most efficient synthetic methods in organic chemistry in the past decades.Recently,our group reported a novel three-component reaction in which oxonium ylides generated in-situ from diazo compounds catalyzed by Rh(Ⅱ) with alcohols underwent nucleophilic addition to aldehydes.
Furthermore,it demonstrated that electron-rich and less hindered alcohols favored the alcoholic oxonium ylide formation and gave the three-component products in good yield.Interestingly,we found that water served as a "active alcohol" which generated oxonium ylide trapped by electron-deficient aryl aldehydes to afford a three-component product in excellent yield.It is worth noting that this approach should be practically applied to efficiently constructα,β-dihydroxyl ester derivatives in[bmim]PF_6 and water biphasic system.The starting materials are cheap and this method is regarded as an available way to effectively constructα,β-dihydroxyl ester derivatives.We reuse this biphasic medium and catalyst for several times for the purpose of green chemistry.Meanwhile,we take advantage of ICP technology to Study the relationship between recycled reaction medium and remained catalyst.
methyl 3-acetyl-1H-pyrrole-2-carboxylate is some sort of compound which is used for medicine.The total synthetic method is thoroughly studied under optimal condition.
(S)-azetidine-2-carboxylic acid precursor is also studied with a relatively new way which is good for chemical processing.
Some sort of dithiophen compound and furan compound are synthesized by optimal method.
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