由α-乙酰基环丙烷基酰胺衍生物构建几种杂环化合物的合成研究
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摘要
环丙烷衍生物不仅存在于多种天然产物及具有药物活性分子的结构中,而且,由于具有高选择性开环反应性质,该类化合物己被作为一类重要的有机合成中间体,广泛应用于多种天然产物、药物分子以及重要复杂分子的合成。因此,自从慕尼黑有机化学家William Henry Perkin[1]在实验室第一次合成环丙烷衍生物以来,对该类化合物的合成以及开环反应研究一直受到有机合成化学家和药物化学家的高度重视。
在该研究领域中,α-乙酰基环丙烷基酰胺类化合物不仅含有氧和氮等亲核杂原子,同时由于双羰基活化作用,使该类化合物具有很高的反应活性。近年来,对该类化合物在各种碳环、杂环以及稠环化合物合成中的应用研究引起人们广泛关注。然而,相对而言,人们对带有炔基的α-乙酰基环丙烷基酰胺类化合物的开环反应的应用研究以及α-乙酰基环丙烷基酰胺类化合物和异氰基乙酸乙酯的成环反应的研究却十分有限。
本论文以多官能化的α-乙酰基环丙烷基酰胺类化合物为起始原料,重点研究该类化合物与异氰基乙酸乙酯的成环反应以及含有炔基结构单元的α-乙酰基环丙烷基酰胺类化合物的开环和成环反应,合成了一系列重要的氮环和稠杂环类化合物。具体研究内容如下：
1.在Cu2O催化下,成功实现了α-乙酰基环丙烷基酰胺类化合物与异氰基乙酸乙酯分子内成环反应,制备一系列重要的噁唑类化合物。在此基础上,通过控制反应条件,调控反应取向,获得多种重要吡啶酮类化合物。
2.以含有炔基结构单元的α-乙酰基环丙烷基酰胺类化合物为底物,在TsOH·H2O作用下,成功实现该类环丙烷类化合物开环反应以及随后的分子内炔基胺化反应,制备一系列重要的多取代吡咯酮类化合物。
3.在t-BuOK作碱的条件下,成功实现氮原子上含有丙炔基的α-乙酰基环丙烷基酰胺类化合物分子内连续的多米诺成环反应,制备一系列重要的呋喃[3,2-b]-γ-内酰胺类衍生物,为该类化合物在有机化学以及药物化学等领域中的进一步应用奠定了坚实的基础。
4.以丙炔胺类化合物和硫代插烯式硫酯类化合物分别为1,3-偶极子和Cz-亲偶极体,在水相中,成功实现碱驱动或催化二者连续的[3+2]环合反应和随后脱乙酰基或1,2-酰基迁移反应,获得多种重要的多取代吡咯类衍生物。
本文合成了许多的新化合物,并对其进行了1H-NMR、13C-NMR等数据表征。
Cyclopropane derivatives exists in structures of various natural products and moleculeswith medicinal reactivity, due to having a high selectivity for the nature of the ring-openingreaction, the kind of chemical compound is regarded as important organic synthesisintermediate which is widely applied in synthesis of various natural products, medicinalmolecules, and complex molecules. Therefore, since the first cyclopropane derivatives weresynthesized by William Henry Perkin in Munich in the laboratory of the eminent chemistAdolf von Baeyer, the chemists of synthetic and medicinal Chemistry have attached greatattention to the synthesis of the compounds as well as the ring-opening reaction research.
In research of this area,-acetyllcyclopropanylamide not only has nucleophilicheteroatoms like oxygen and nitrogen, but also has double activation of carbonyl, so that thesecompounds have high reactivity. In recent years, the study of the compounds in the synthesisof various carbocyclic and heterocyclic compounds fused on ring has caused widespreadconcern. However, researches in ring-opening reaction of-acetyllcyclopropanylamide withalkynyl and cyclization reaction of ethyl isocyanoacetate is very limited.
In this thesis, taking polyfunctional-acetyllcyclopropanylamide as original material,focuses on cyclization reaction of this compound and ethyl isocyanoacetate, as well asring-opening and cyclization reaction of-acetyllcyclopropanylamide with alkynyl unit, andsynthetised a series of important nitrogen ring and heterocycle compound. The followingstatements are the brief of my work.First, a series of oxazole compounds were obtained via AuCl3-catalyzed the successiveintermolecular condensation and intramolecular cyclization reaction of
-acetyllcyclopropanylamide and ethyl isocyanoacetate. Basing on this, various importantpyridine compounds are obtained through controlling reaction conditions.Second, a series of polysubstituted pyrollidone compounds were obtained via the action ofTsOH H2O, taking-acetyllcyclopropanylamide with alkynyl unit as substrate, ring-openingreaction and the subsequent intramolecular alkynylamine reaction.Third, a series of furan[3,2-b]--lactam compounds were obtained via the action of t-BuOK,domino reactions of-acetyllcyclopropanylamide with alkynyl on nitrogen-atomsnitrogen-atoms. All this laid a solid foundation on further application in organic chemistry andmedicinal chemistry.
Fourth, various important polysubstituted pyrrole derivatives are obtained via [3+2] Cycloadditionsof-acyl ketene dithioacetals with propargylamines and1,2-acyl migration reaction, whichare under base actiom, taking propargylamines compounds and thioester interpolation olefinic compounds as1,3–dipole and C2-dipolarophile.
In this thesis, many new compounds were synthesized and characterized by confirmed by1HNMR and13CNMR spectroscopies.
在该研究领域中,α-乙酰基环丙烷基酰胺类化合物不仅含有氧和氮等亲核杂原子,同时由于双羰基活化作用,使该类化合物具有很高的反应活性。近年来,对该类化合物在各种碳环、杂环以及稠环化合物合成中的应用研究引起人们广泛关注。然而,相对而言,人们对带有炔基的α-乙酰基环丙烷基酰胺类化合物的开环反应的应用研究以及α-乙酰基环丙烷基酰胺类化合物和异氰基乙酸乙酯的成环反应的研究却十分有限。
本论文以多官能化的α-乙酰基环丙烷基酰胺类化合物为起始原料,重点研究该类化合物与异氰基乙酸乙酯的成环反应以及含有炔基结构单元的α-乙酰基环丙烷基酰胺类化合物的开环和成环反应,合成了一系列重要的氮环和稠杂环类化合物。具体研究内容如下：
1.在Cu2O催化下,成功实现了α-乙酰基环丙烷基酰胺类化合物与异氰基乙酸乙酯分子内成环反应,制备一系列重要的噁唑类化合物。在此基础上,通过控制反应条件,调控反应取向,获得多种重要吡啶酮类化合物。
2.以含有炔基结构单元的α-乙酰基环丙烷基酰胺类化合物为底物,在TsOH·H2O作用下,成功实现该类环丙烷类化合物开环反应以及随后的分子内炔基胺化反应,制备一系列重要的多取代吡咯酮类化合物。
3.在t-BuOK作碱的条件下,成功实现氮原子上含有丙炔基的α-乙酰基环丙烷基酰胺类化合物分子内连续的多米诺成环反应,制备一系列重要的呋喃[3,2-b]-γ-内酰胺类衍生物,为该类化合物在有机化学以及药物化学等领域中的进一步应用奠定了坚实的基础。
4.以丙炔胺类化合物和硫代插烯式硫酯类化合物分别为1,3-偶极子和Cz-亲偶极体,在水相中,成功实现碱驱动或催化二者连续的[3+2]环合反应和随后脱乙酰基或1,2-酰基迁移反应,获得多种重要的多取代吡咯类衍生物。
本文合成了许多的新化合物,并对其进行了1H-NMR、13C-NMR等数据表征。
Cyclopropane derivatives exists in structures of various natural products and moleculeswith medicinal reactivity, due to having a high selectivity for the nature of the ring-openingreaction, the kind of chemical compound is regarded as important organic synthesisintermediate which is widely applied in synthesis of various natural products, medicinalmolecules, and complex molecules. Therefore, since the first cyclopropane derivatives weresynthesized by William Henry Perkin in Munich in the laboratory of the eminent chemistAdolf von Baeyer, the chemists of synthetic and medicinal Chemistry have attached greatattention to the synthesis of the compounds as well as the ring-opening reaction research.
In research of this area,-acetyllcyclopropanylamide not only has nucleophilicheteroatoms like oxygen and nitrogen, but also has double activation of carbonyl, so that thesecompounds have high reactivity. In recent years, the study of the compounds in the synthesisof various carbocyclic and heterocyclic compounds fused on ring has caused widespreadconcern. However, researches in ring-opening reaction of-acetyllcyclopropanylamide withalkynyl and cyclization reaction of ethyl isocyanoacetate is very limited.
In this thesis, taking polyfunctional-acetyllcyclopropanylamide as original material,focuses on cyclization reaction of this compound and ethyl isocyanoacetate, as well asring-opening and cyclization reaction of-acetyllcyclopropanylamide with alkynyl unit, andsynthetised a series of important nitrogen ring and heterocycle compound. The followingstatements are the brief of my work.First, a series of oxazole compounds were obtained via AuCl3-catalyzed the successiveintermolecular condensation and intramolecular cyclization reaction of
-acetyllcyclopropanylamide and ethyl isocyanoacetate. Basing on this, various importantpyridine compounds are obtained through controlling reaction conditions.Second, a series of polysubstituted pyrollidone compounds were obtained via the action ofTsOH H2O, taking-acetyllcyclopropanylamide with alkynyl unit as substrate, ring-openingreaction and the subsequent intramolecular alkynylamine reaction.Third, a series of furan[3,2-b]--lactam compounds were obtained via the action of t-BuOK,domino reactions of-acetyllcyclopropanylamide with alkynyl on nitrogen-atomsnitrogen-atoms. All this laid a solid foundation on further application in organic chemistry andmedicinal chemistry.
Fourth, various important polysubstituted pyrrole derivatives are obtained via [3+2] Cycloadditionsof-acyl ketene dithioacetals with propargylamines and1,2-acyl migration reaction, whichare under base actiom, taking propargylamines compounds and thioester interpolation olefinic compounds as1,3–dipole and C2-dipolarophile.
In this thesis, many new compounds were synthesized and characterized by confirmed by1HNMR and13CNMR spectroscopies.
引文
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