α-官能化二硫缩烯酮与Vilsmeier试剂和草酰氯的多米诺反应研究
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摘要
自1910年Kelber首次合成了α-苯甲酰基二甲硫缩烯酮,经过近百年的发展,α-羰基二硫缩烯酮化学已经在有机合成化学中占据了重要一席,特别是近三十年来发展更快,每年都有相当数量的文章出现,并有数篇综述对这些工作进行了总结。一般来说,基于α-羰基二硫缩烯酮化学的反应主要为:与金属有机试剂的选择性加成反应,与氮亲核体的共轭加成反应,α-碳原子的亲核性及相关反应,烷硫基作为硫醇的替代试剂的应用,α-羰基二硫缩烯酮在碳环、杂环化合物合成中的应用等。
在众多的α-羰基二硫缩烯酮类化合物中,α-乙酰基-α-胺甲酰基二硫缩烯酮和α-烯酰基二硫缩烯酮具有容易制备,官能团多等特点。我们小组在以前的工作中对α-乙酰基-α-胺甲酰基二硫缩烯酮在合成中的应用进行了深入的研究,如与醛缩合生成α-烯酰基-α-胺甲酰基二硫缩烯酮,将其作为1,5-双亲电五碳合成子的[5+1]成环策略等。但对其与Vilsmeier试剂的反应研究却很少。另外,对于α-烯酰基二硫缩烯酮的研究则主要集中在其作为3C或5C合成子的研究上,其α-位的官能化研究只是停留在溴化、硝化、脱羧等简单的反应之上,而对α-位C-C键的形成还缺乏足够的认识。因此,α-乙酰基-α-胺甲酰基二硫缩烯酮与Vilsmeier试剂的分子内环合反应和α-烯酰基二硫缩烯酮α-位C-C键的形成反应及其在合成中的应用研究是很重要的研究课题。
发展新的基元反应和新的合成方法是有机化学创新进步的基础。在本课题组常年从事α-羰基二硫缩烯酮化学研究的基础上,本论文利用合成设计、以α-乙酰基-α-胺甲酰基二硫缩烯酮和α-烯酰基二硫缩烯酮的合成为工作基础,以发展新基元合成反应和合成新方法为目标,创建了新的成环策略,由此建立了一种通用性强、步骤简洁的合成卤代吡啶酮、桥环[3.3.1]壬烷类化合物、吡咯烷三酮化合物的新方法。论文工作主要包括以下四个方面的内容。
1.研究了α-乙酰基-α-胺甲酰基二硫缩烯酮化合物与Vilsmeier试剂的反应,成功制备了一系列4-卤代-2-吡啶酮类化合物,为卤代吡啶酮的合成提供了一条简洁,高效的新路线。
2.实现了α-烯酰基二硫缩烯酮与草酰氯的多米诺反应,获得了一系列γ-亚烷基丁烯羟酸内脂类化合物。该产物不仅是一类多官能团化合物,而且具有很强的反应活性,是一类非常重要的有机合成中间体。
3.在BF3·Et2O催化下,成功实现了γ-亚烷基丁烯羟酸内脂类化合物的分子内Michael加成反应,立体选择性地制备了一系列多官能化桥环[3.3.1]壬烷类化合物。实验结果表明,该反应具有很高的原子经济性。
4.通过α-酰胺基二硫缩烯酮和草酰氯的反应,成功制备了一系列吡咯烷酮类化合物。该反应操作简单,材料易得且产率很高,为吡咯烷酮的合成提供了新方法。
Since Kelber first synthesized theα-Benzoyl ketene-(S,S)-acetal in 1910,α-oxo ketene-(S,S)-acetals chemistry has become an important division in organic chemistry through the development of nearly one hundred years. Especially in the past three decades, quite amount of documents have been published in this field, and several reviews reported and summarized these findings. Generally speaking, the reaction types involvingα-oxoketene-(S,S)-acetals mainly include the regioselective addition-aromatization with organometallic reagents, conjugate addition-cyclization with nitrogen nucleophilicspecies, nucleophilic reactions ofα-carbon, acting as odorless dithiol equivalentsin thioacetalization, Michael additions and [5+1] annulation, as well as the synthetic applications based on the above reactions.
Among the variousα-Oxo ketene-(S,S)-acetals,α-acetyl-α-carbamoyl ketene-(S,S)- acetals andα-alkenoyl ketene-(S,S)-acetals are easier to prepare and bear much more functionalities. We have had the extensive studies on theα-acetyl-α-carbamoyl ketene-(S,S)-acetals and its further applications, for example, their adols condensations with aldehydes giveα-alkenoyl-α-carbamoyl ketene-(S,S)-acetals which can be utilized as the 1,5-bielectronic five-carbon components to react with various binucleophlilic species in a [5+1] annulation. However, researches onα-acetyl-α-carbamoyl ketene-(S,S)-acetals with Vilsmeier reagents remained poorly explored. In addition,α-alkenoyl ketene-(S,S)-acetals mainly used as the synthons of 3C and 5C, theα-functionalized reactions of which just limited on some simple reactions, as bromination, nitration, acetylation. However, the understanding of the forming of C-C bond atα-position is far from enough. Therefore, studies and applications of the intramolecular cyclization betweenα-acetyl-α-carbamoyl ketene-(S,S)-acetals and Vilsmeier reagents, the C-C bond formation atα-position ofα-alkenoyl ketene-(S,S)-acetals are research projects of great significance.
Developments of new basic reactions and new synthetic methods are the basis for the innovation and advancement of organic chemistry. Based on the research achievement of our group inα-oxo ketene-(S,S)-acetal chemistry in the past decades, my thesis starts from the synthesis ofα-acetyl-α-carbamoyl ketene-(S,S)-acetals andα-alkenoyl ketene-(S,S)-acetals through synthetic design, aiming to develop new basic reactions and new synthetic methods for interesting cyclic molecules and consequently found a new synthetic strategy to provide a general and simple route to halogenated pyridinones, bicycle[3.3.1]nonanes, pyrrolidinetriones. The thesis mainly includes the following four aspects.
1. Investigate the reaction ofα-acetyl-α-carbamoyl ketene-(S,S)-acetals with Vilsmeier reagents and synthesis a rang of 4-halogenated N-substituted 2(1H)-pyridinones.
2. The Domino reactions ofα-alkenoyl ketene-(S,S)-acetals and oxalyl chloride were carried out, and theγ-alkylidenebutenolides were obtained in good yield. These compounds can be potentially useful intermediates in organic synthesis due to the multifunctionality in the molecules.
3. In the presence of BF3·Et2O, the intramolecular Michael addition ofγ-alkylidenebut- enolides were performed and generated the corresponding bicycle[3.3.1]nonanes compounds. The above experimental results revealed that the reactions have very high atom economical manner.
4. By the reactions ofα-acylamino ketene-(S,S)-acetals and oxalyl chloride, a serie of pyrrolidinetriones were prepared. The simple procedure, mild condition,easy separation, high yield, make this protocol most attractive for synthesis of pyrrolidinetriones.
在众多的α-羰基二硫缩烯酮类化合物中,α-乙酰基-α-胺甲酰基二硫缩烯酮和α-烯酰基二硫缩烯酮具有容易制备,官能团多等特点。我们小组在以前的工作中对α-乙酰基-α-胺甲酰基二硫缩烯酮在合成中的应用进行了深入的研究,如与醛缩合生成α-烯酰基-α-胺甲酰基二硫缩烯酮,将其作为1,5-双亲电五碳合成子的[5+1]成环策略等。但对其与Vilsmeier试剂的反应研究却很少。另外,对于α-烯酰基二硫缩烯酮的研究则主要集中在其作为3C或5C合成子的研究上,其α-位的官能化研究只是停留在溴化、硝化、脱羧等简单的反应之上,而对α-位C-C键的形成还缺乏足够的认识。因此,α-乙酰基-α-胺甲酰基二硫缩烯酮与Vilsmeier试剂的分子内环合反应和α-烯酰基二硫缩烯酮α-位C-C键的形成反应及其在合成中的应用研究是很重要的研究课题。
发展新的基元反应和新的合成方法是有机化学创新进步的基础。在本课题组常年从事α-羰基二硫缩烯酮化学研究的基础上,本论文利用合成设计、以α-乙酰基-α-胺甲酰基二硫缩烯酮和α-烯酰基二硫缩烯酮的合成为工作基础,以发展新基元合成反应和合成新方法为目标,创建了新的成环策略,由此建立了一种通用性强、步骤简洁的合成卤代吡啶酮、桥环[3.3.1]壬烷类化合物、吡咯烷三酮化合物的新方法。论文工作主要包括以下四个方面的内容。
1.研究了α-乙酰基-α-胺甲酰基二硫缩烯酮化合物与Vilsmeier试剂的反应,成功制备了一系列4-卤代-2-吡啶酮类化合物,为卤代吡啶酮的合成提供了一条简洁,高效的新路线。
2.实现了α-烯酰基二硫缩烯酮与草酰氯的多米诺反应,获得了一系列γ-亚烷基丁烯羟酸内脂类化合物。该产物不仅是一类多官能团化合物,而且具有很强的反应活性,是一类非常重要的有机合成中间体。
3.在BF3·Et2O催化下,成功实现了γ-亚烷基丁烯羟酸内脂类化合物的分子内Michael加成反应,立体选择性地制备了一系列多官能化桥环[3.3.1]壬烷类化合物。实验结果表明,该反应具有很高的原子经济性。
4.通过α-酰胺基二硫缩烯酮和草酰氯的反应,成功制备了一系列吡咯烷酮类化合物。该反应操作简单,材料易得且产率很高,为吡咯烷酮的合成提供了新方法。
Since Kelber first synthesized theα-Benzoyl ketene-(S,S)-acetal in 1910,α-oxo ketene-(S,S)-acetals chemistry has become an important division in organic chemistry through the development of nearly one hundred years. Especially in the past three decades, quite amount of documents have been published in this field, and several reviews reported and summarized these findings. Generally speaking, the reaction types involvingα-oxoketene-(S,S)-acetals mainly include the regioselective addition-aromatization with organometallic reagents, conjugate addition-cyclization with nitrogen nucleophilicspecies, nucleophilic reactions ofα-carbon, acting as odorless dithiol equivalentsin thioacetalization, Michael additions and [5+1] annulation, as well as the synthetic applications based on the above reactions.
Among the variousα-Oxo ketene-(S,S)-acetals,α-acetyl-α-carbamoyl ketene-(S,S)- acetals andα-alkenoyl ketene-(S,S)-acetals are easier to prepare and bear much more functionalities. We have had the extensive studies on theα-acetyl-α-carbamoyl ketene-(S,S)-acetals and its further applications, for example, their adols condensations with aldehydes giveα-alkenoyl-α-carbamoyl ketene-(S,S)-acetals which can be utilized as the 1,5-bielectronic five-carbon components to react with various binucleophlilic species in a [5+1] annulation. However, researches onα-acetyl-α-carbamoyl ketene-(S,S)-acetals with Vilsmeier reagents remained poorly explored. In addition,α-alkenoyl ketene-(S,S)-acetals mainly used as the synthons of 3C and 5C, theα-functionalized reactions of which just limited on some simple reactions, as bromination, nitration, acetylation. However, the understanding of the forming of C-C bond atα-position is far from enough. Therefore, studies and applications of the intramolecular cyclization betweenα-acetyl-α-carbamoyl ketene-(S,S)-acetals and Vilsmeier reagents, the C-C bond formation atα-position ofα-alkenoyl ketene-(S,S)-acetals are research projects of great significance.
Developments of new basic reactions and new synthetic methods are the basis for the innovation and advancement of organic chemistry. Based on the research achievement of our group inα-oxo ketene-(S,S)-acetal chemistry in the past decades, my thesis starts from the synthesis ofα-acetyl-α-carbamoyl ketene-(S,S)-acetals andα-alkenoyl ketene-(S,S)-acetals through synthetic design, aiming to develop new basic reactions and new synthetic methods for interesting cyclic molecules and consequently found a new synthetic strategy to provide a general and simple route to halogenated pyridinones, bicycle[3.3.1]nonanes, pyrrolidinetriones. The thesis mainly includes the following four aspects.
1. Investigate the reaction ofα-acetyl-α-carbamoyl ketene-(S,S)-acetals with Vilsmeier reagents and synthesis a rang of 4-halogenated N-substituted 2(1H)-pyridinones.
2. The Domino reactions ofα-alkenoyl ketene-(S,S)-acetals and oxalyl chloride were carried out, and theγ-alkylidenebutenolides were obtained in good yield. These compounds can be potentially useful intermediates in organic synthesis due to the multifunctionality in the molecules.
3. In the presence of BF3·Et2O, the intramolecular Michael addition ofγ-alkylidenebut- enolides were performed and generated the corresponding bicycle[3.3.1]nonanes compounds. The above experimental results revealed that the reactions have very high atom economical manner.
4. By the reactions ofα-acylamino ketene-(S,S)-acetals and oxalyl chloride, a serie of pyrrolidinetriones were prepared. The simple procedure, mild condition,easy separation, high yield, make this protocol most attractive for synthesis of pyrrolidinetriones.
引文
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[10] For selected examples, see: [5C + 1C] annulations and related reactions: (a) Bi X., Dong D., Liu Q., et al. [5 + 1] Annulation: A Synthetic Strategy for Highly Substituted Phenols and Cyclohexenones [J] J. Am. Chem. Soc., 2005, 127, 4578-4579; (b) Zhang L., Liang F., Cheng X., Liu Q. Efficient Synthesis of Highly Functionalized Dihydropyrido [2,3-d]pyrimidines by a Double Annulation Strategy fromα-Alkenoyl-α-carbamoyl Ketene-(S,S)-acetals [J] J. Org. Chem., 2009, 74, 899-902; (c) Zhang Q., Sun S., Hu J., Liu Q., Tan J. BF3·Et2O-Catalyzed Direct Carbon-Carbon Bond Formation ofα-EWG Ketene-(S,S)-Acetals and Alcohols and Synthesis of Unsymmetrical Biaryls [J] J. Org. Chem., 2007, 72, 139-143.
[11] For selected examples, see: [5C+1N] annulations (a) Dong D., Bi X., Liu Q. and Cong F. [5C+1N] Annulation: A Novel Synthetic Strategy for Functionalized 2,3-dihydro-4- 2,3-dihydro-4-pyridones [J] Chem. Commun., 2005, 3580-3582; (b) Zhao L., Liang F., Bi X., Sun S. and Liu Q. Efficient Synthesis of Highly Functionalized Dihydropyrido [2,3-d]pyrimidines by a Double Annulation Strategy fromα-Alkenoyl-α-carbamoyl Ketene-(S,S)-acetals [J] J. Org. Chem., 2006, 71, 1094-1098; (c) Hu J., Zhang Q., Yuan H., Liu, Q. Temperature-Controlled Synthesis of Substituted Pyridine Derivatives via the [5C+1N] Annulation of 1,1-Bisalkylthio-1,4-pentanedienes and Ammonium Acetate [J] J. Org. Chem., 2008, 73, 2442-2445; [5C+1S] annulations (d) Bi X., Dong D., Li Y. and Liu Q. A Facile and Efficient Synthetic Route toward Functionalized 2,3-Dihydrothiopyran-4-ones [J] J. Org. Chem., 2005, 70, 10886-10889; [5C+1Se] annulations Li D., Xiu X., Liu Q. and Dong S. [J] Synthesis, 2008, 1895-1901.
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[10] For selected examples, see: [5C + 1C] annulations and related reactions: (a) Bi X., Dong D., Liu Q., et al. [5 + 1] Annulation: A Synthetic Strategy for Highly Substituted Phenols and Cyclohexenones [J] J. Am. Chem. Soc., 2005, 127, 4578-4579; (b) Zhang L., Liang F., Cheng X., Liu Q. Efficient Synthesis of Highly Functionalized Dihydropyrido [2,3-d]pyrimidines by a Double Annulation Strategy fromα-Alkenoyl-α-carbamoyl Ketene-(S,S)-acetals [J] J. Org. Chem., 2009, 74, 899-902; (c) Zhang Q., Sun S., Hu J., Liu Q., Tan J. BF3·Et2O-Catalyzed Direct Carbon-Carbon Bond Formation ofα-EWG Ketene-(S,S)-Acetals and Alcohols and Synthesis of Unsymmetrical Biaryls [J] J. Org. Chem., 2007, 72, 139-143.
[11] For selected examples, see: [5C+1N] annulations (a) Dong D., Bi X., Liu Q. and Cong F. [5C+1N] Annulation: A Novel Synthetic Strategy for Functionalized 2,3-dihydro-4- 2,3-dihydro-4-pyridones [J] Chem. Commun., 2005, 3580-3582; (b) Zhao L., Liang F., Bi X., Sun S. and Liu Q. Efficient Synthesis of Highly Functionalized Dihydropyrido [2,3-d]pyrimidines by a Double Annulation Strategy fromα-Alkenoyl-α-carbamoyl Ketene-(S,S)-acetals [J] J. Org. Chem., 2006, 71, 1094-1098; (c) Hu J., Zhang Q., Yuan H., Liu, Q. Temperature-Controlled Synthesis of Substituted Pyridine Derivatives via the [5C+1N] Annulation of 1,1-Bisalkylthio-1,4-pentanedienes and Ammonium Acetate [J] J. Org. Chem., 2008, 73, 2442-2445; [5C+1S] annulations (d) Bi X., Dong D., Li Y. and Liu Q. A Facile and Efficient Synthetic Route toward Functionalized 2,3-Dihydrothiopyran-4-ones [J] J. Org. Chem., 2005, 70, 10886-10889; [5C+1Se] annulations Li D., Xiu X., Liu Q. and Dong S. [J] Synthesis, 2008, 1895-1901.
[12] For C-C bond-forming reactions atα-position of functionalized ketene S,S-acetals with aldehydes, ketones or unsaturated ketones, see: (a) Yuan H.-J., Wang M., Liu Y.-J. and Liu Q. Copper(II)-Catalyzed C-C Bond-Forming Reactions ofα-Electron Withdrawing Group-Substituted Ketene S,S-Acetals with Carbonyl Compounds and a Facile Synthesis of Coumarins [J] Adv. Synth. Catal., 2009, 351, 112-116; (b) Fu Z., Wang M., Ma Y., Liu Q. and Liu J. Synthesis of Functionalized Allylic Sulfoxides and Their Use in the Construction of 2,3,4-Trisubstituted Furans via a [3+2] Annulation [J] J. Org. Chem., 2008, 73, 7625-7630; (c) Yin Y., Wang M., Liu Q., Hu J., Sun S. and Kang J. A C-C Bond Formation Reaction at Theα-Carbon Atom of α-Oxo Ketene Dithioacetals via The Baylis–Hillman Type Reaction [J] Tetrahedron Lett., 2005, 46, 4399-4402; (d) Zhang Q., Liu Y., Wang M., Liu Q., Hu J. and Yin Y. Highly Efficient C-C Bond Forming Reactions ofα-Cyanoketene Dithioacetal withAldehydes,α-Ketoester and Ketones [J] Synthesis, 2006, 3009-3014.
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