炔丙醇与二硫缩烯酮的碳/杂环化反应
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摘要
杂环、碳环作为关键结构单元广泛地存在于天然产物、合成药物、染料、以及有机功能材料中，发展新的成环反应，一直是有机合成化学研究的核心内容。制备新型多官能化有机合成子进而构建所需环系，是发展成环新反应的主要策略。因此，创造性地设计和制备多官能化、多反应位点的有机合成子是有机合成方法学研究的重要内容。炔和二硫缩烯酮均是具有代表性的有机合成子，已有百余年的研究历史。有机化学家利用两者的结构特点及取代基的立体、电子效应等因素，开发了众多碳环以及杂环化合物的合成新策略，形成了特色鲜明的合成方法学。如果能将二者“融合”成新的有机合成子（使其兼具炔和二硫缩烯酮的结构特征），所得的合成子将具有重要的应用价值。
我们课题组一直致力于炔化学研究，根据多年的研究经验提出了‘官能化炔’的研究新思路。作为具有代表性的一类‘官能化炔’，炔丙醇在路易斯酸作用下易于生成炔基碳正离子，能够与亲核性物种反应，生成新的‘官能化炔’；同时，炔基碳正离子能够重排生成联烯基碳正离子。二硫缩烯酮是另一类易于制备的合成中间体，其α-位具有强亲核性，易于与亲电物种反应。基于炔丙醇和二硫缩烯酮化合物的这些反应特性，我们创造性地将二者结合，通过构建炔基/二硫缩烯酮‘融合’的合成中间体，进一步发生分子内的环合反应，或直接进行分子间的成环反应，从而为一些重要碳、杂环化合物的合成提供新方法。本论文主要分为五个章节。
第一章：介绍炔丙醇类化合物在有机合成中的应用。
第二章：概要性介绍二硫缩烯酮化学的研究进展。
第三章：阐述论文选题。
第四章：我们以三氟化硼乙醚作催化剂，实现了炔丙醇和α-羰基二硫缩烯酮的[3+2]环加成反应，以较高的收率得到全取代环戊二烯。其中，α-羰基二硫缩烯酮首次作为极化的烯烃合成碳环化合物，通过对反应机理研究，我们发现了在闭环过程中一个新颖的1,4-烷硫基迁移。进一步研究发现，环戊二烯中独特的取代基促使和马来酰亚胺反应，并发现了一种新颖的脱烷硫基型Diels-Alder反应，得到一类新型的有机小分子荧光染料，具有易于大量制备、易于结构修饰等优点，并且具有优良的光物理性质。
第五章：利用炔丙醇在路易斯酸作用下易于生成炔基碳正离子的特点，能够与二硫缩烯酮α-位发生偶联反应，得到多种含有二硫缩烯酮的‘官能化炔’。此类合成子进一步发生分子内或分子间的环合反应，最终我们得到多取代吡咯、噻吩、二氢噻吩和苯并[f]-1-二氢茚酮等重要的化合物。
Carbon/heterocyclic ring as a key structural element widely found in natural products,synthetic drugs, dyes, and organic functional materials, the development of a new cyclization,has been the core content of organic synthetic chemistry research. Preparation of newmulti-functional organic synthesis and thus build the required sub-ring system, is developinginto a new ring main policy response. Therefore, creatively designed and preparedmulti-functional, multi-site reactions in organic synthon is an important part of organicsynthesis research. Alkyne and ketene dithioacetals are representative organic synthons, overa hundred years of research history. Organic chemists use structural features of both stereoand replace factors, electronic effects and other factors to develop a new strategy for thesynthesis of a number of carbocyclic and heterocyclic compounds, forming a distinctivesynthesis methodology. If you can both "fusion" into a new organic synthon (make structuralfeatures of both alkyne and ketene dithioacetals), and the resulting synthon will haveimportant applications.
Our group has been working alkyne chemistry research, the 'functionalized alkyne'research new ideas based on years of research experience. As a representative of a class of'functionalized alkyne', propargyl alcohols in the presence of lewis acid easy to producealkynyl carbocation can be reacted with a nucleophilic species to produce new 'functionalizedalkyne'; Meanwhile, alkynyl carbocations rearrangement can generate allenic carbocations. α-carbonyl ketene dithioacetals is easy to prepare a synthetic intermediate, the α-position has astrong nucleophilicity to react with the electrophilic species. Based on the responsecharacteristics of propargyl alcohols and ketene dithioacetals, we creatively combine both bybuilding alkynyl/ketene dithioacetals 'fusion' synthetic intermediates, further intramolecularcyclization occurs, or to direct intermolecular cyclization reaction to provide a new methodfor the synthesis of a number of important carbo/heterocyclic compounds. The thesis isdivided into five chapters.
The first chapter introduces the propargyl alcohols compound used in organic synthesis.
The second chapter, the significant advances in the chemistry of ketene dithioacetals inrecent years are reviewed.
The third chapter of the paper topic.
The IV chapter, we have developed a conceptually new strategy to synthesizecyclopentadienes by BF3Et2O-catalyzed regiospecific [3+2] cycloaddition of propargylic alcohols and α-oxo ketene dithioacetals. The α-oxo ketene dithioacetals were for the first timeapplied to carbocyclic synthesis as polarized alkenes. A mechanistically novel1,4-alkylthioshift was observed in the ring-closure process. The unique substitution pattern ofcyclopentadienes facilitated an unusual dethiolation Diels–Alder reaction with maleimides,affording a new small organic fluorescent dye molecules, with ease a lot of preparation, easeof structural modification, etc., and has excellent photophysical properties.
Chapter V, the containing ketene dithioacetals 'functionalized alkyne' were efficientlyconstructed through a coupling reaction of propargyl cabocations from propargylic alcoholswith ketene dithioacetals. Further the use of such synthons intermolecular or intramolecularcyclization reaction, we finally obtain several important compounds, such as polysubstitutedpyrroles, thiophenes, dihydrothiophenes and benzo[f]-1-indanones and so on.
我们课题组一直致力于炔化学研究，根据多年的研究经验提出了‘官能化炔’的研究新思路。作为具有代表性的一类‘官能化炔’，炔丙醇在路易斯酸作用下易于生成炔基碳正离子，能够与亲核性物种反应，生成新的‘官能化炔’；同时，炔基碳正离子能够重排生成联烯基碳正离子。二硫缩烯酮是另一类易于制备的合成中间体，其α-位具有强亲核性，易于与亲电物种反应。基于炔丙醇和二硫缩烯酮化合物的这些反应特性，我们创造性地将二者结合，通过构建炔基/二硫缩烯酮‘融合’的合成中间体，进一步发生分子内的环合反应，或直接进行分子间的成环反应，从而为一些重要碳、杂环化合物的合成提供新方法。本论文主要分为五个章节。
第一章：介绍炔丙醇类化合物在有机合成中的应用。
第二章：概要性介绍二硫缩烯酮化学的研究进展。
第三章：阐述论文选题。
第四章：我们以三氟化硼乙醚作催化剂，实现了炔丙醇和α-羰基二硫缩烯酮的[3+2]环加成反应，以较高的收率得到全取代环戊二烯。其中，α-羰基二硫缩烯酮首次作为极化的烯烃合成碳环化合物，通过对反应机理研究，我们发现了在闭环过程中一个新颖的1,4-烷硫基迁移。进一步研究发现，环戊二烯中独特的取代基促使和马来酰亚胺反应，并发现了一种新颖的脱烷硫基型Diels-Alder反应，得到一类新型的有机小分子荧光染料，具有易于大量制备、易于结构修饰等优点，并且具有优良的光物理性质。
第五章：利用炔丙醇在路易斯酸作用下易于生成炔基碳正离子的特点，能够与二硫缩烯酮α-位发生偶联反应，得到多种含有二硫缩烯酮的‘官能化炔’。此类合成子进一步发生分子内或分子间的环合反应，最终我们得到多取代吡咯、噻吩、二氢噻吩和苯并[f]-1-二氢茚酮等重要的化合物。
Carbon/heterocyclic ring as a key structural element widely found in natural products,synthetic drugs, dyes, and organic functional materials, the development of a new cyclization,has been the core content of organic synthetic chemistry research. Preparation of newmulti-functional organic synthesis and thus build the required sub-ring system, is developinginto a new ring main policy response. Therefore, creatively designed and preparedmulti-functional, multi-site reactions in organic synthon is an important part of organicsynthesis research. Alkyne and ketene dithioacetals are representative organic synthons, overa hundred years of research history. Organic chemists use structural features of both stereoand replace factors, electronic effects and other factors to develop a new strategy for thesynthesis of a number of carbocyclic and heterocyclic compounds, forming a distinctivesynthesis methodology. If you can both "fusion" into a new organic synthon (make structuralfeatures of both alkyne and ketene dithioacetals), and the resulting synthon will haveimportant applications.
Our group has been working alkyne chemistry research, the 'functionalized alkyne'research new ideas based on years of research experience. As a representative of a class of'functionalized alkyne', propargyl alcohols in the presence of lewis acid easy to producealkynyl carbocation can be reacted with a nucleophilic species to produce new 'functionalizedalkyne'; Meanwhile, alkynyl carbocations rearrangement can generate allenic carbocations. α-carbonyl ketene dithioacetals is easy to prepare a synthetic intermediate, the α-position has astrong nucleophilicity to react with the electrophilic species. Based on the responsecharacteristics of propargyl alcohols and ketene dithioacetals, we creatively combine both bybuilding alkynyl/ketene dithioacetals 'fusion' synthetic intermediates, further intramolecularcyclization occurs, or to direct intermolecular cyclization reaction to provide a new methodfor the synthesis of a number of important carbo/heterocyclic compounds. The thesis isdivided into five chapters.
The first chapter introduces the propargyl alcohols compound used in organic synthesis.
The second chapter, the significant advances in the chemistry of ketene dithioacetals inrecent years are reviewed.
The third chapter of the paper topic.
The IV chapter, we have developed a conceptually new strategy to synthesizecyclopentadienes by BF3Et2O-catalyzed regiospecific [3+2] cycloaddition of propargylic alcohols and α-oxo ketene dithioacetals. The α-oxo ketene dithioacetals were for the first timeapplied to carbocyclic synthesis as polarized alkenes. A mechanistically novel1,4-alkylthioshift was observed in the ring-closure process. The unique substitution pattern ofcyclopentadienes facilitated an unusual dethiolation Diels–Alder reaction with maleimides,affording a new small organic fluorescent dye molecules, with ease a lot of preparation, easeof structural modification, etc., and has excellent photophysical properties.
Chapter V, the containing ketene dithioacetals 'functionalized alkyne' were efficientlyconstructed through a coupling reaction of propargyl cabocations from propargylic alcoholswith ketene dithioacetals. Further the use of such synthons intermolecular or intramolecularcyclization reaction, we finally obtain several important compounds, such as polysubstitutedpyrroles, thiophenes, dihydrothiophenes and benzo[f]-1-indanones and so on.
引文
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