基于串联反应稠杂环化合物的合成研究
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摘要
串联反应与多组分反应是当今有机化学的研究前沿和热点领域之一,在天然产物的全合成、杂环化合物的构建、组合化学等领域具有广泛地应用。本论文系统地研究了利用串联反应与多组分反应合成一系列结构较为复杂、新颖,部分为原创性母核的杂环化合物。最大限度使起始原料转化为目标产物,避免中间体的分离而带来的资源浪费,体现原子经济性、合成效率的有效性和环境的友好性,而且也为杂环骨架构筑的方法学提供有价值的补充。主要内容和结果如下：
1.发展了一个新的高效的自催化串联反应,首次合成了多取代的二螺[4.2.5.2]十五烷-9,13-二酮。对称双醛亚胺与麦氏酸在醋酸溶液中反应,高立体选择性地生成多取代螺[5.5]十一烷-1,5,9-三酮衍生物；当该体系中存在乙二醇时,生成二螺[4.2.5.2]十五烷二酮衍生物。手性的二醇也能给出相应的产物。实现了在温和的条件下乙二醇对羰基的保护,并提供了一步合成二螺杂环体系新的有效地合成方法。反应过程中产生乙酰肼,它能作为催化剂催化Barbas二烯胺粤亚苄基麦氏酸发生Diels-Alder反应。对反应机理进行了研究,并进一步确证了乙酰肼为该反应的自催化剂。
2. (1)发展了1,8-二氧代-2,3,4,5,6,7-六氢氧杂蒽与水合肼的串联反应：脂肪基取代的1,8-二氧代-2,3,4,5,6,7-六氢氧杂蒽与水合肼反应,经历分子间和分子内的有次序的开环、环化、迁移、再开环、再环化和芳构化组成的串联反应,高产率合成了四环斯诺啉并[5,4,3-cde]斯诺啉衍生物。此外,芳基取代的1,8-二氧代-2,3,4,5,6,7-六氢氧杂蒽与水合肼反应,提供N-氨基吖啶,产率优良。通过对取代基的有效控制,实现产物的化学选择性,并解释化学选择性的影响因素。
(2)发展了一个新的、高区域选择性和碘促进下的串联反应：2-氨基吡喃-3腈和异氰酸酯为原料,在微波辐射下,经历开环和再环化过程,高产率提供N-取代-2氨基喹啉衍生物。该反应具有反应时间短(20-36min),产率和区域选择性高,操作简单方便等优点,避免繁琐的分离过程。
3.发现了一种氰乙酰胺、环酮和芳香醛的四组分串联反应：氰乙酰胺、环酮和芳香醛反应分别生成两个缩合中间体,再经历[4+2]环加成反应产生原创性母核的吡啶并[3,4-i]喹唑啉类化合物,同时一步新形成两个环、五个σ键和四个立体基因中心包括一个氨化的季碳中心。用脂肪醛或环酮代替芳香醛时,该反应经历另一个不同反应途径,生成三环[5.2.2.01,5]十一烷和[6.2.2.01,6]十二烷衍生物。该反应使起始原料最大限度转化为目标产物,副产物仅为水或二氧化碳,避免中间体的分离而带来的资源浪费,体现原子经济、成键经济和结构经济。
4.发展了微波促进的炔酸酯与醛、胺的三组分反应合成了各种取代的吡咯烷酮类化合物,产物都经过严格的表征,产物结构由单晶衍射确定。我们提出了一个较为可行的反应机理。其次,对炔酸酯与氰乙酰胺、硫代异腈酸酯的串联反应进行了考察。为了避免了副反应的发生,先将硫代异腈酸酯与氰乙酰胺缩合,不分离加入过量的醋酸和等当量的炔酸酯,以几乎定量的收率合成了噻唑酮类化合物。
5.发展了微波促进的丙二腈参与的多组分串联反应：(1)发现了丙二腈、环酮、醋酸铵的新的多组分串联反应,该反应涉及缩合、亲核加成、环化和开环等过程。(2)将底物环酮调整为芳酮时,则得到多氰基取代的吡啶衍生物。将其再与醋酸铵反应,发现了一个新的、罕见的串联反应。(3)发展了一种A2B2型串联反应,在碱性催化剂存在下,2分子的丙二睛与2分子的环酮发生串联反应,生成复杂的螺环化合物。
Domino reactions and Multi-component reactions (MCRs) have been highlighted as one of research frontier, widely used for the construction of heterocycles and in total synthesis and combinatorial chemistry. In this thesis, a series of novel heterocyclic compounds involving in more complex structures and in part original nucleus were synthesized based on domino reactions and MCRs. The starting materials have been maximized to convert into the desired compounds, avoiding time-consuming and energy-costing processes that involve multi-step syntheses. So, these reactions have the advantage of atom economy, high synthetic efficiency and environmental friendliness, which offer a valuable addendum to methodology for the synthesis of heterocycles. The discussions and results are listed as following:
PartⅠ:The first synthesis of poly-substituted dispiro[4.2.5.2] pentadecane-9, 13-dione based on new, efficient domino autocatalytic reaction has been developed. The symmetric double imines reacted with Meldrum's acid in HOAc to provide poly-substituted spiro[5.5]undecanes with high stereoselectivity. When the reaction was carried out in mixed solvent of HOAc and ethylene glycol, interestingly, new dispiro[4.2.5.2]pentadecanes was furnished with ethylene glycol as a protection reagent of carbonyl group under this mild reaction condition. The chiral 1,2-propanediol (S-) also gave the corresponding dispiro[4.2.5.2]pentadecanes. The key step to spiro[5.5]undecanes was that acetohydrazide from the reaction system catalyzed Diels-Alder reaction between Barbas dienamine and arylidene-Meldrum's acid. The study on the reaction mechanism indicated that acetohydrazide as a self-catalyst was served for the reaction. The methodology provides a new approach to the synthesis of dispiro system.
PartⅡ:(a) the novel domino reaction of 1,8-dioxo-2,3,4,5,6,7-hexahydroanthenes with hydrazine hydrate has been developed. The domino reaction involved intermolecular and intramolecular ring-opening/cyclization/rearrangement/ re-ring-opening/re-cyclization/aromatization process. In addition, 1,8-dioxo-2,3,4,5,6,7-hexahydroanthenes with aryl-groups (R1) reacted with hydrazine hydrate to N-amino-1,8-dioxoacridines with good to excellent yields. The reaction chemoselectivity was controlled by the steric effect.
(b) A new iodine-promoted domino reaction of 2-aminochromene-3-carbonitriles with various isocyanates was described, and a set of polyfunctionalized N-substituted 2-aminoquinoline-3-carbonitriles with high regioselectivity were successfully synthesized under microwave heating. In this reaction, the ring-opening/recyclization process occurs unexpectedly at the ring of 4H-pyran with different isocyanates. The syntheses were finished within short periods (20-36 min) with good to excellent chemical yields and regioselectivity that avoided tedious work-up isolations.
PartⅢ:a novel four-component domino reaction by employing simple aldehydes, cycloketones and cyanoamides has been discovered. Two different Knoevenagel intermediates from the reaction of simple aldehydes, cycloketones and cyanoamides underwent [4+2] cyclization to generate pyrido[3,4-i]quinazoline derivatives possessing original nucleus with concomitant new formation of up to two rings, fiveσbonds and four quaternary carbon centers with one quaternary carbon-amino function. The replacement of their aliphatic counterparts (or cycloketones) with aromatic aldehydes was examined, and the reaction occurred to another direction to form multi-functionalized tricyclo[5.2.2.01,5]undecanes and tricyclo[6.2.2.01,6]dodecane. The reaction is very fast and can be finished within short period and with water or CO2 as the major byproduct, which makes work-up convenient, which show the superiority of atom economy, bond economy and structure economy.
PartⅣ:The microwave-assisted synthesis of a variety of new substituted pyrrolidones via the three-component reaction of acetylene esters and aldehydes, amines has been developed. The structure is established by NMR and X-ray analysis, and a possible mechanism for the domino process was proposed. Secondly, a tandem reaction of acetylene esters cyanoamides and thio-isocyanide ester were studied. In order to avoid the formation of by-products, thio-isocyanide was condensed with cyanoamides. Without isolation, the excessive amount of acetic acid and acetylene esters was added into the mixture, providing thiazole ketones in quantitative yields.
Part V:The microwave-assisted multi-component tandem reactions of malononitrile were developed. (1) The new domino reaction of malononitrile, cyclic ketones and ammonium acetate was discovered. The reaction underwent a domino intermolecular and intramolecular condensation-addition-cyclization-recyclization sequence. (2) Instead of cyclic ketones, the arones reacted with malononitrile to give the more cyano-substituted pyridine derivatives, which further reacted with ammonium acetate to 1,6-naphthyridine-8-carbonitriles. So the new domino reaction was described. (2) The base-catalyzed A2B2-type reaction of malononitrile (2.0 equiv.) with cyclic ketones (2.0 equiv.) was developed.
1.发展了一个新的高效的自催化串联反应,首次合成了多取代的二螺[4.2.5.2]十五烷-9,13-二酮。对称双醛亚胺与麦氏酸在醋酸溶液中反应,高立体选择性地生成多取代螺[5.5]十一烷-1,5,9-三酮衍生物；当该体系中存在乙二醇时,生成二螺[4.2.5.2]十五烷二酮衍生物。手性的二醇也能给出相应的产物。实现了在温和的条件下乙二醇对羰基的保护,并提供了一步合成二螺杂环体系新的有效地合成方法。反应过程中产生乙酰肼,它能作为催化剂催化Barbas二烯胺粤亚苄基麦氏酸发生Diels-Alder反应。对反应机理进行了研究,并进一步确证了乙酰肼为该反应的自催化剂。
2. (1)发展了1,8-二氧代-2,3,4,5,6,7-六氢氧杂蒽与水合肼的串联反应：脂肪基取代的1,8-二氧代-2,3,4,5,6,7-六氢氧杂蒽与水合肼反应,经历分子间和分子内的有次序的开环、环化、迁移、再开环、再环化和芳构化组成的串联反应,高产率合成了四环斯诺啉并[5,4,3-cde]斯诺啉衍生物。此外,芳基取代的1,8-二氧代-2,3,4,5,6,7-六氢氧杂蒽与水合肼反应,提供N-氨基吖啶,产率优良。通过对取代基的有效控制,实现产物的化学选择性,并解释化学选择性的影响因素。
(2)发展了一个新的、高区域选择性和碘促进下的串联反应：2-氨基吡喃-3腈和异氰酸酯为原料,在微波辐射下,经历开环和再环化过程,高产率提供N-取代-2氨基喹啉衍生物。该反应具有反应时间短(20-36min),产率和区域选择性高,操作简单方便等优点,避免繁琐的分离过程。
3.发现了一种氰乙酰胺、环酮和芳香醛的四组分串联反应：氰乙酰胺、环酮和芳香醛反应分别生成两个缩合中间体,再经历[4+2]环加成反应产生原创性母核的吡啶并[3,4-i]喹唑啉类化合物,同时一步新形成两个环、五个σ键和四个立体基因中心包括一个氨化的季碳中心。用脂肪醛或环酮代替芳香醛时,该反应经历另一个不同反应途径,生成三环[5.2.2.01,5]十一烷和[6.2.2.01,6]十二烷衍生物。该反应使起始原料最大限度转化为目标产物,副产物仅为水或二氧化碳,避免中间体的分离而带来的资源浪费,体现原子经济、成键经济和结构经济。
4.发展了微波促进的炔酸酯与醛、胺的三组分反应合成了各种取代的吡咯烷酮类化合物,产物都经过严格的表征,产物结构由单晶衍射确定。我们提出了一个较为可行的反应机理。其次,对炔酸酯与氰乙酰胺、硫代异腈酸酯的串联反应进行了考察。为了避免了副反应的发生,先将硫代异腈酸酯与氰乙酰胺缩合,不分离加入过量的醋酸和等当量的炔酸酯,以几乎定量的收率合成了噻唑酮类化合物。
5.发展了微波促进的丙二腈参与的多组分串联反应：(1)发现了丙二腈、环酮、醋酸铵的新的多组分串联反应,该反应涉及缩合、亲核加成、环化和开环等过程。(2)将底物环酮调整为芳酮时,则得到多氰基取代的吡啶衍生物。将其再与醋酸铵反应,发现了一个新的、罕见的串联反应。(3)发展了一种A2B2型串联反应,在碱性催化剂存在下,2分子的丙二睛与2分子的环酮发生串联反应,生成复杂的螺环化合物。
Domino reactions and Multi-component reactions (MCRs) have been highlighted as one of research frontier, widely used for the construction of heterocycles and in total synthesis and combinatorial chemistry. In this thesis, a series of novel heterocyclic compounds involving in more complex structures and in part original nucleus were synthesized based on domino reactions and MCRs. The starting materials have been maximized to convert into the desired compounds, avoiding time-consuming and energy-costing processes that involve multi-step syntheses. So, these reactions have the advantage of atom economy, high synthetic efficiency and environmental friendliness, which offer a valuable addendum to methodology for the synthesis of heterocycles. The discussions and results are listed as following:
PartⅠ:The first synthesis of poly-substituted dispiro[4.2.5.2] pentadecane-9, 13-dione based on new, efficient domino autocatalytic reaction has been developed. The symmetric double imines reacted with Meldrum's acid in HOAc to provide poly-substituted spiro[5.5]undecanes with high stereoselectivity. When the reaction was carried out in mixed solvent of HOAc and ethylene glycol, interestingly, new dispiro[4.2.5.2]pentadecanes was furnished with ethylene glycol as a protection reagent of carbonyl group under this mild reaction condition. The chiral 1,2-propanediol (S-) also gave the corresponding dispiro[4.2.5.2]pentadecanes. The key step to spiro[5.5]undecanes was that acetohydrazide from the reaction system catalyzed Diels-Alder reaction between Barbas dienamine and arylidene-Meldrum's acid. The study on the reaction mechanism indicated that acetohydrazide as a self-catalyst was served for the reaction. The methodology provides a new approach to the synthesis of dispiro system.
PartⅡ:(a) the novel domino reaction of 1,8-dioxo-2,3,4,5,6,7-hexahydroanthenes with hydrazine hydrate has been developed. The domino reaction involved intermolecular and intramolecular ring-opening/cyclization/rearrangement/ re-ring-opening/re-cyclization/aromatization process. In addition, 1,8-dioxo-2,3,4,5,6,7-hexahydroanthenes with aryl-groups (R1) reacted with hydrazine hydrate to N-amino-1,8-dioxoacridines with good to excellent yields. The reaction chemoselectivity was controlled by the steric effect.
(b) A new iodine-promoted domino reaction of 2-aminochromene-3-carbonitriles with various isocyanates was described, and a set of polyfunctionalized N-substituted 2-aminoquinoline-3-carbonitriles with high regioselectivity were successfully synthesized under microwave heating. In this reaction, the ring-opening/recyclization process occurs unexpectedly at the ring of 4H-pyran with different isocyanates. The syntheses were finished within short periods (20-36 min) with good to excellent chemical yields and regioselectivity that avoided tedious work-up isolations.
PartⅢ:a novel four-component domino reaction by employing simple aldehydes, cycloketones and cyanoamides has been discovered. Two different Knoevenagel intermediates from the reaction of simple aldehydes, cycloketones and cyanoamides underwent [4+2] cyclization to generate pyrido[3,4-i]quinazoline derivatives possessing original nucleus with concomitant new formation of up to two rings, fiveσbonds and four quaternary carbon centers with one quaternary carbon-amino function. The replacement of their aliphatic counterparts (or cycloketones) with aromatic aldehydes was examined, and the reaction occurred to another direction to form multi-functionalized tricyclo[5.2.2.01,5]undecanes and tricyclo[6.2.2.01,6]dodecane. The reaction is very fast and can be finished within short period and with water or CO2 as the major byproduct, which makes work-up convenient, which show the superiority of atom economy, bond economy and structure economy.
PartⅣ:The microwave-assisted synthesis of a variety of new substituted pyrrolidones via the three-component reaction of acetylene esters and aldehydes, amines has been developed. The structure is established by NMR and X-ray analysis, and a possible mechanism for the domino process was proposed. Secondly, a tandem reaction of acetylene esters cyanoamides and thio-isocyanide ester were studied. In order to avoid the formation of by-products, thio-isocyanide was condensed with cyanoamides. Without isolation, the excessive amount of acetic acid and acetylene esters was added into the mixture, providing thiazole ketones in quantitative yields.
Part V:The microwave-assisted multi-component tandem reactions of malononitrile were developed. (1) The new domino reaction of malononitrile, cyclic ketones and ammonium acetate was discovered. The reaction underwent a domino intermolecular and intramolecular condensation-addition-cyclization-recyclization sequence. (2) Instead of cyclic ketones, the arones reacted with malononitrile to give the more cyano-substituted pyridine derivatives, which further reacted with ammonium acetate to 1,6-naphthyridine-8-carbonitriles. So the new domino reaction was described. (2) The base-catalyzed A2B2-type reaction of malononitrile (2.0 equiv.) with cyclic ketones (2.0 equiv.) was developed.
引文
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