基于DMAD引发的两可性离子合成新型杂环化合物的方法学研究
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摘要
多组分反应(MCR)固有的原子经济性、会聚性、高产率、多样性等特点,使MCR成为小分子化学库强有力的合成方法。这种方法比起其他经典的逐步反应具有显著的优点,因此,MCR在药物发现、农药化学和天然产物全合成等方面得到广泛的应用。
两可性离子通常来自于亲核试剂和像DMAD这样的活泼炔烃的加成反应。众所周知的亲核试剂诸如三苯基膦、嘧啶、叔胺、二甲基亚砜等都可以由此路径制得两可性离子。
全文充分发挥多组分“一锅煮”反应的优越性,基于两可性离子作为中间体,合成制备了目标杂环化合物。
论文第一章以吡啶为诱发剂,以取代苯甲醛和丁炔二酸二甲酯(DMAD)为原料反应得到重要的有机中间体2-芳甲酰基丁烯二酸二甲酯,不经分离原位与苯肼进行多组分一锅煮反应,合成了6个3-(取代苯基)-1-苯基-4,5-二氢-1H-吡唑-4,5-二羧酸二甲酯吡唑类化合物1a-1f。
第二章以菲啶、DMAD和取代苯甲醛为原料进行三组分一锅煮反应合成了11个二甲基-2-(芳基)-2,13b-二氢-[1,3]氧嗪[3,2-f]菲啶-3,4二羧酸酯的氧嗪菲啶类衍生物2a-2i′。通过对比溶剂和温度对反应的影响,最终确定以二氯甲烷为溶剂,室温反应为最佳反应条件制备目标化合物。
第三章通过对化合物1b, 2c进行单晶培养以及晶体结构解析,最终确定所合成目标化合物的正确性。
全文合成的所有新化合物的结构均经IR、1H NMR、13C NMR、MS或HRMS验证,证明了化合物结构的正确性,同时通过对所培养的化合物1b, 2c的单晶的Χ-射线衍射分析,确定了目标化合物精确的空间构型。
Due to the atom economy, convergent character, high yields and diversity, multi-component reactions (MCRs) have become a powerful method for the synthesis of small-molecule libraries. This approach offers significant advantages over classical stepwise approaches, so MCRs are widely used in discovery of medicine, agricultural chemistry and synthesis of natural products.
Zwitterionic species often come from the addition of nucleophiles to activated alkynes like dimethyl acetylenedicarboxylate (DMAD). A variety of nucleophiles such as triphenyl phosphine (PPh3), pyridine, tertiary amine, dimethyl sulfoxide etc.has been known to generate zwitterionic species by this pathway.
In this paper, one-pot multi-component synthetic method combined with zwitterionic species was uesd for generating the target heterocyclic compounds.
In the first chapter, dimethyl 2-benzoylfumarate, which was an important intermediate, was synthesized from arylaldehydes with dimethyl acetylene- dicarboxylate (DMAD), catalyzed by pyridine. Then it reacted with phenylhydrazine in situ. In this way, six dimethyl 3-(aryl)-1-phenyl-4,5-dihydro-1H-pyrazole-4,5- dicarboxylates 1a-1f were synthesized through one-pot four-component reaction.
In the second chapter, eleven dimethyl 2-(aryl)-2,13b-dihydro-[1,3]oxazino [3,2-f]phenanthridine-3,4-dicarboxylate derivatives 2a-2i′was synthesized by the zwitterion generated by the addition of nucleophiles phenanthridine to activated alkynes dimethyl acetylenedicarboxylate (DMAD) with substituted benzaldehyde through one-pot three-component reaction. Different solvents and the reaction temperature for this MCR were investigated. Using CH2Cl2 as solvent at room temperature were deemed to the optimum reaction condition.
In the third chapter, two single-crystals (1b, 2c) were cultured and the structure of the compounds were ultimately characterized byΧ-ray single-crystal diffraction analysis.
The structures of all the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, MS or HRMS. Two single-crystals were cultured and the structure of the unknown compounds could be confirmed conveniently byΧ-ray single-crystal diffraction analysis.
两可性离子通常来自于亲核试剂和像DMAD这样的活泼炔烃的加成反应。众所周知的亲核试剂诸如三苯基膦、嘧啶、叔胺、二甲基亚砜等都可以由此路径制得两可性离子。
全文充分发挥多组分“一锅煮”反应的优越性,基于两可性离子作为中间体,合成制备了目标杂环化合物。
论文第一章以吡啶为诱发剂,以取代苯甲醛和丁炔二酸二甲酯(DMAD)为原料反应得到重要的有机中间体2-芳甲酰基丁烯二酸二甲酯,不经分离原位与苯肼进行多组分一锅煮反应,合成了6个3-(取代苯基)-1-苯基-4,5-二氢-1H-吡唑-4,5-二羧酸二甲酯吡唑类化合物1a-1f。
第二章以菲啶、DMAD和取代苯甲醛为原料进行三组分一锅煮反应合成了11个二甲基-2-(芳基)-2,13b-二氢-[1,3]氧嗪[3,2-f]菲啶-3,4二羧酸酯的氧嗪菲啶类衍生物2a-2i′。通过对比溶剂和温度对反应的影响,最终确定以二氯甲烷为溶剂,室温反应为最佳反应条件制备目标化合物。
第三章通过对化合物1b, 2c进行单晶培养以及晶体结构解析,最终确定所合成目标化合物的正确性。
全文合成的所有新化合物的结构均经IR、1H NMR、13C NMR、MS或HRMS验证,证明了化合物结构的正确性,同时通过对所培养的化合物1b, 2c的单晶的Χ-射线衍射分析,确定了目标化合物精确的空间构型。
Due to the atom economy, convergent character, high yields and diversity, multi-component reactions (MCRs) have become a powerful method for the synthesis of small-molecule libraries. This approach offers significant advantages over classical stepwise approaches, so MCRs are widely used in discovery of medicine, agricultural chemistry and synthesis of natural products.
Zwitterionic species often come from the addition of nucleophiles to activated alkynes like dimethyl acetylenedicarboxylate (DMAD). A variety of nucleophiles such as triphenyl phosphine (PPh3), pyridine, tertiary amine, dimethyl sulfoxide etc.has been known to generate zwitterionic species by this pathway.
In this paper, one-pot multi-component synthetic method combined with zwitterionic species was uesd for generating the target heterocyclic compounds.
In the first chapter, dimethyl 2-benzoylfumarate, which was an important intermediate, was synthesized from arylaldehydes with dimethyl acetylene- dicarboxylate (DMAD), catalyzed by pyridine. Then it reacted with phenylhydrazine in situ. In this way, six dimethyl 3-(aryl)-1-phenyl-4,5-dihydro-1H-pyrazole-4,5- dicarboxylates 1a-1f were synthesized through one-pot four-component reaction.
In the second chapter, eleven dimethyl 2-(aryl)-2,13b-dihydro-[1,3]oxazino [3,2-f]phenanthridine-3,4-dicarboxylate derivatives 2a-2i′was synthesized by the zwitterion generated by the addition of nucleophiles phenanthridine to activated alkynes dimethyl acetylenedicarboxylate (DMAD) with substituted benzaldehyde through one-pot three-component reaction. Different solvents and the reaction temperature for this MCR were investigated. Using CH2Cl2 as solvent at room temperature were deemed to the optimum reaction condition.
In the third chapter, two single-crystals (1b, 2c) were cultured and the structure of the compounds were ultimately characterized byΧ-ray single-crystal diffraction analysis.
The structures of all the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, MS or HRMS. Two single-crystals were cultured and the structure of the unknown compounds could be confirmed conveniently byΧ-ray single-crystal diffraction analysis.
引文
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