基于N-磺酰基联烯胺中间体的串联反应研究
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摘要
串联反应来构筑杂环化合物和碳环化合物是当代有机化学家的研究热点,在药物分子和天然产物合成中具有广泛应用。本论文在总结了近年来稳定的联烯酰胺的制备和联烯酰胺在杂环化合物和碳环化合物构筑取得的一系列进展的基础上,研究和发展了炔丙醇与磺酰胺的各种反应。主要内容是基于N-磺酰基联烯胺中间体的串联反应。内容如下：
1)炔丙醇、磺酰胺和NIS串联反应合成茚类化合物
发展了一种新的N-磺酰基联烯胺的产生方式,并且用活泼的亲电试剂将其捕获,从而发展了一种包含炔丙醇、.磺酰胺、NIS的三组分串联反应。通过这种合成策略,我们可以从简单易得的起始原料出发,高效地合成2-碘茚类化合物,一锅法可以构筑C-C,C-N,C-I三个δ键。该反应产率中等至良好,条件温和,反应时间短。含碘的产物为之后的衍生化提供了可能性。
2)2-(3-羟基-1-丙炔)苯磺酰胺串联反应合成螺环化合物
发展了2-(3-羟基-1-丙炔)苯磺酰胺在Lewis酸催化下的分子内反应,成功地构筑了螺环化合物。该反应操作简便,反应条件温和。通过对机理的研究,我们认为a,β-不饱和酮是该反应的关键中间体。
3)炔丙醇和腙串联反应合成二氢吡唑类化合物
发展了由炔丙醇和腙在BF3·Et2O催化下合成二氢吡唑类化合物的方法。该方法操作简单,条件温和,起始原料简单易得,底物范围广。一个可能的机理被提出,机理包含N-磺酰基联烯胺的形成和1,2-磺酰基迁移。更有意义的是,3,3-二芳基丙烯腈类化合物可以通过所合成的二氢吡唑类化合物的N-N键断裂得到。
4)炔丙醇和羟胺串联反应合成二氢异嗯唑类化合物
发展了一种炔丙醇和N-磺酰基羟胺在Lewis酸催化下合成2,5-二氢异嗯唑和4-碘(溴)-2,5-二氢异嗯唑类化合物的方法。该方法不需要使用特殊的π-酸催化剂,反应条件温和,原料简单易得。N-磺酰基联烯胺被认为是关键中间体。所得的4-碘-2,5-二氢异嗯唑类化合物可以通过Pd催化的羰基化反应得到4,5-二氢异嗯唑-4-羧酸甲酯类化合物。
As a research hotspot, Construction of heterocycles and carbocycles via tandem reaction is widely used for the synthesis of drug molecules and natural products. In the thesis, preparation of stable allenamides (an effective and versatile building block) and construction of heterocycles and carbocycles by the development of allenamides' reaction has been reviewed. We have constructed several complex skeletons from propargylic alcohols and sulfonamides, mostly via N-sulfonyl allenamide intermediate. The details are summarized as following:
1) Synthesis of indenes
An efficient method to generate N-sulfonyl allenamide intermediate, which could be captured by electrophiles was developed. In this process, a facile and efficient three-component domino reaction involving propargylic alcohol, sulfonamide, NIS was investigated. Highly substituted2-iodoindenes were generated from readily accessible and simple starting materials via this synthetic strategy. Consequently,three δ-bonds were efficiently constructed in this one-pot reaction, including C-C, C-N, and C-I δ-bonds. The possibility of derivatization by cross-coupling reaction was provided by the products containing C-I δ-bond.
2) Synthesis of spiro compounds
An efficient method to generate spiro compounds via Lewis acid catalyzed intramolecular reaction of2-(3-hydroxyprop-l-yn-l-yl) benzenesulfonamide was developed. The reaction was mild and easily operated, α,β-Unsaturated carbonyl compound is postulated to be the key intermediate for the tandem transformation.
3) Synthesis of dihydropyrazoles
An efficient strategy to synthesize4-methylene-4,5-dihydro-1H-pyrazoles was developed via a BF3·Et2O catalyzed domino reaction of propargylic alcohols and N-sulfonylhydrazones. The reaction was mild and easily operated. The starting material was easily prepared and a wide range of substrates could apply to the tandem reaction leading to the formation of different4,5-dihydropyrazoles. A tentative mechanism was postulated, and N-sulfonyl allenamide intermediate is postulated to be the key intermediate, which was formed by trapping the in situ generating allenic carbocation with N-sulfonylhydrazone. More significantly,3,3-diarylacrylonitriles, which might be served for potential utility in cancer chemotherapy, could be efficiently obtained from the synthesized4-methylene-4,5-dihydro-1H-pyrazoles via N-N bond cleavage in excellent yields.
4) Synthesis of dihydroisoxazoles
An efficient methodology to synthesize2,5-Dihydroisoxazoles,4-iodo-2,5-dihydroisoxazoles and4-bromo-2,5-dihydroisoxazoles was provided from propargyl alcohols and TsNHOH using Yb(OTf)3, iodine and the combination of NBS and Yb(OTf)3, respectively. N-sulfonyl allenamide is postulated to be the key intermediate for these tandem transformations, which was formed by trapping the in situ generating allenic carbocation with TsNHOH. Moreover, the resulting4-iodo-2,5-dihydroisoxazoles could be elaborated by Pd-catalyzed carbonylation to generate4-methoxycarbonyl-4,5-dihydroisoxazoles.
1)炔丙醇、磺酰胺和NIS串联反应合成茚类化合物
发展了一种新的N-磺酰基联烯胺的产生方式,并且用活泼的亲电试剂将其捕获,从而发展了一种包含炔丙醇、.磺酰胺、NIS的三组分串联反应。通过这种合成策略,我们可以从简单易得的起始原料出发,高效地合成2-碘茚类化合物,一锅法可以构筑C-C,C-N,C-I三个δ键。该反应产率中等至良好,条件温和,反应时间短。含碘的产物为之后的衍生化提供了可能性。
2)2-(3-羟基-1-丙炔)苯磺酰胺串联反应合成螺环化合物
发展了2-(3-羟基-1-丙炔)苯磺酰胺在Lewis酸催化下的分子内反应,成功地构筑了螺环化合物。该反应操作简便,反应条件温和。通过对机理的研究,我们认为a,β-不饱和酮是该反应的关键中间体。
3)炔丙醇和腙串联反应合成二氢吡唑类化合物
发展了由炔丙醇和腙在BF3·Et2O催化下合成二氢吡唑类化合物的方法。该方法操作简单,条件温和,起始原料简单易得,底物范围广。一个可能的机理被提出,机理包含N-磺酰基联烯胺的形成和1,2-磺酰基迁移。更有意义的是,3,3-二芳基丙烯腈类化合物可以通过所合成的二氢吡唑类化合物的N-N键断裂得到。
4)炔丙醇和羟胺串联反应合成二氢异嗯唑类化合物
发展了一种炔丙醇和N-磺酰基羟胺在Lewis酸催化下合成2,5-二氢异嗯唑和4-碘(溴)-2,5-二氢异嗯唑类化合物的方法。该方法不需要使用特殊的π-酸催化剂,反应条件温和,原料简单易得。N-磺酰基联烯胺被认为是关键中间体。所得的4-碘-2,5-二氢异嗯唑类化合物可以通过Pd催化的羰基化反应得到4,5-二氢异嗯唑-4-羧酸甲酯类化合物。
As a research hotspot, Construction of heterocycles and carbocycles via tandem reaction is widely used for the synthesis of drug molecules and natural products. In the thesis, preparation of stable allenamides (an effective and versatile building block) and construction of heterocycles and carbocycles by the development of allenamides' reaction has been reviewed. We have constructed several complex skeletons from propargylic alcohols and sulfonamides, mostly via N-sulfonyl allenamide intermediate. The details are summarized as following:
1) Synthesis of indenes
An efficient method to generate N-sulfonyl allenamide intermediate, which could be captured by electrophiles was developed. In this process, a facile and efficient three-component domino reaction involving propargylic alcohol, sulfonamide, NIS was investigated. Highly substituted2-iodoindenes were generated from readily accessible and simple starting materials via this synthetic strategy. Consequently,three δ-bonds were efficiently constructed in this one-pot reaction, including C-C, C-N, and C-I δ-bonds. The possibility of derivatization by cross-coupling reaction was provided by the products containing C-I δ-bond.
2) Synthesis of spiro compounds
An efficient method to generate spiro compounds via Lewis acid catalyzed intramolecular reaction of2-(3-hydroxyprop-l-yn-l-yl) benzenesulfonamide was developed. The reaction was mild and easily operated, α,β-Unsaturated carbonyl compound is postulated to be the key intermediate for the tandem transformation.
3) Synthesis of dihydropyrazoles
An efficient strategy to synthesize4-methylene-4,5-dihydro-1H-pyrazoles was developed via a BF3·Et2O catalyzed domino reaction of propargylic alcohols and N-sulfonylhydrazones. The reaction was mild and easily operated. The starting material was easily prepared and a wide range of substrates could apply to the tandem reaction leading to the formation of different4,5-dihydropyrazoles. A tentative mechanism was postulated, and N-sulfonyl allenamide intermediate is postulated to be the key intermediate, which was formed by trapping the in situ generating allenic carbocation with N-sulfonylhydrazone. More significantly,3,3-diarylacrylonitriles, which might be served for potential utility in cancer chemotherapy, could be efficiently obtained from the synthesized4-methylene-4,5-dihydro-1H-pyrazoles via N-N bond cleavage in excellent yields.
4) Synthesis of dihydroisoxazoles
An efficient methodology to synthesize2,5-Dihydroisoxazoles,4-iodo-2,5-dihydroisoxazoles and4-bromo-2,5-dihydroisoxazoles was provided from propargyl alcohols and TsNHOH using Yb(OTf)3, iodine and the combination of NBS and Yb(OTf)3, respectively. N-sulfonyl allenamide is postulated to be the key intermediate for these tandem transformations, which was formed by trapping the in situ generating allenic carbocation with TsNHOH. Moreover, the resulting4-iodo-2,5-dihydroisoxazoles could be elaborated by Pd-catalyzed carbonylation to generate4-methoxycarbonyl-4,5-dihydroisoxazoles.
引文
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[1](a) Froimowitz, M.; Wu, K.-M.; Moussa, A.; Haidar, R. M.; Jurayj, J.; George, C.; Gardner, E. L., Slow-Onset, Long-Duration 3-(3',4'-Dichlorophenyl)-1-indanamine Monoamine Reuptake Blockers as Potential Medications To Treat Cocaine Abuse. J. Med. Chem.2000,43,4981-4992; (b) Yu, H.; Kim, I. J.; Folk, J. E.; Tian, X.; Rothman, R. B.; Baumann, M. H.; Dersch, C. M.; Flippen-Anderson, J. L.; Parrish, D.; Jacobson, A. E.; Rice, K. C., Synthesis and Pharmacological Evaluation of 3-(3,4-Dichlorophenyl)-1-indanamine Derivatives as Nonselective Ligands for Biogenic Amine Transporters. J. Med. Chem.2004,47,2624-2634; (c) Di Stefano, A.; Sozio, P.; Cacciatore, I.; Cocco, A.; Giorgioni, G.; Costa, B.; Montali, M.; Lucacchini, A.; Martini, C.; Spoto, G.; Di Pietrantonio, F.; Di Matteo, E.; Pinnen, F., Preparation and Pharmacological Characterization of trans-2-Amino-5(6)-fluoro-6(5)-hydroxy-l-phenyl-2,3-dihydro-lH-indenes as D2-like Dopamine Receptor Agonists. J. Med. Chem.2005,48,2646-2654.
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[1]Schmidt, A.; Dreger, A., Recent Advances in the Chemistry of Pyrazoles. Properties, Biological Activities, and Syntheses. Curr. Org. Chem.2011,15,1423-1463.
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[9](a) Fang, Z.; Song, Y.; Sarkar, T.; Hamel, E.; Fogler, W. E.; Agoston, G. E.; Fanwick, P. E.; Cushman, M., Stereoselective Synthesis of 3,3-Diarylacrylonitriles as Tubulin Polymerization Inhibitors. J. Org. Chem.2008,73,4241-4244; (b) Zhang, L.-H.; Wu, L.; Raymon, H. K.; Chen, R. S.; Corral, L.; Shirley, M. A.; Krishna Narla, R.; Gamez, J.; Muller, G. W.; Stirling, D. I.; Bartlett, J. B.; Schafer, P. H.; Payvandi, F., The Synthetic Compound CC-5079 Is a Potent Inhibitor of Tubulin Polymerization and Tumor Necrosis Factor-α Production with Antitumor Activity. Cancer Res.2006, 66,951-959.
[1](a) Giomi, D.; Cordero, F. M.; Machetti, F., Isoxazoles. In Comprehensive Heterocyclic Chemistry III, Alan, R. K.; Christopher, A. R.; Eric, F. V. S.; Richard, J. K. T., Eds. Elsevier:Oxford,2008; pp 365-485; (b) Diana, G. D.; McKinlay, M. A.; Brisson, C. J.; Zalay, E. S.; Miralles, J. V.; Salvador, U. J., Isoxazoles with antipicornavirus activity. J. Med. Chem.1985,28,748-752; (c) Guiles, J. W.; Diana, G. D.; Pevear, D. C., [(Biaryloxy)alkyl]isoxazoles:Picornavirus Inhibitors. J. Med. Chem.1995,38,2780-2783; (d) Habeeb, A. G.; Praveen Rao, P. N.; Knaus, E. E., Design and Synthesis of 4,5-Diphenyl-4-isoxazolines:Novel Inhibitors of Cyclooxygenase-2 with Analgesic and Antiinflammatory Activity. J. Med. Chem. 2001,44,2921-2927; (e) Niho, N.; Kitamura, T.; Takahashi, M.; Mutoh, M.; Sato, H.; Matsuura, M.; Sugimura, T.; Wakabayashi, K., Suppression of azoxymethane-induced colon cancer development in rats by a cyclooxygenase-1 selective inhibitor, mofezolac. Cancer Sci.2006,97,1011-1014.
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[3](a) Yang, R.-H.; Chan, W.-H.; Lee, A. W. M.; Xia, P.-F.; Zhang, H.-K., A Ratiometric Fluorescent Sensor for AgI with High Selectivity and Sensitivity. J. Am. Chem. Soc.2003,125,2884-2885; (b) Haino, T.; Tanaka, M.; Ideta, K.; Kubo, K.; Mori, A.; Fukazawa, Y, Solid-phase synthesis of liquid crystalline isoxazole library. Tetrahedron Lett.2004,45,2277-2279.
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[10]Similar works, see:(a) Debleds, O.; Zotto, C. D.; Vrancken, E.; Campagne, J.-M.; Retailleau, P., A Dual Gold-Iron Catalysis for a One-Pot Synthesis of 2,3-Dihydroisoxazoles from Propargylic Alcohols and N-Protected Hydroxylamines. Adv. Synth. Catal.2009,351,1991-1998; (b) Debleds, O.; Gayon, E.; Ostaszuk, E.; Vrancken, E.; Campagne, J.-M., A Versatile Iron-Catalyzed Protocol for the One-Pot Synthesis of Isoxazoles or Isoxazolines from the Same Propargylic Alcohols. Chem. Eur. J.2010,16,12207-12213; (c) Debleds, O.; Gayon, E.; Vrancken, E.; Campagne, J.-M., Gold-catalyzed propargylic substitutions:Scope and synthetic developments. Beilstein Journal of Organic Chemistry 2011,7,866-877; (d) Gayon, E.; Quinonero, O.; Lemouzy, S.; Vrancken, E.; Campagne, J.-M., Transition-Metal-Catalyzed Uninterrupted Four-Step Sequence to Access Trisubstituted Isoxazoles. Org. Lett. 2011,15,6418-6421.
[11]Andres, J.; Cardenas, R; Silla, E.; Tapia, O., A theoretical study of the Meyer-Schuster reaction mechanism:minimum-energy profile and properties of transition-state structure. J. Am. Chem. Soc.1988,110,666-674.
[12](a) Bauer, L.; Exner, O., The Chemistry of Hydroxamic Acids and N-Hydroxyimides. Angew. Chem., Int. Ed.1974,13,376-384; (b) Bohm, S.; Exner, O., Acidity of hydroxamic acids and amides. Org. Biomol. Chem.2003,1, 1176-1180.
[13]For recent reviews, see:(a) Brennfuhrer, A.; Neumann, H.; Beller, M., Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds. Angew. Chem. Int. Ed.2009,48,4114-4133; (b) D'Souza, D. M.; Muller, T. J. J., Multi-component syntheses of heterocycles by transition-metal catalysis. Chem. Soc. Rev.2007,36,1095-1108.
[14]Zadrozna, I.; Kurkowska, J.; Kruszewska, H.; Makuch, I., 4,5-Dihydroisoxazoles:Testing of antimicrobial activity. Il Farmaco 2000,55, 499-501.