SSC  >> Vol. 2 No. 1 (March 2014)

    New Progresses of Multicomponent Reactions Based on Isocyanides

  • 全文下载: PDF(484KB) HTML    PP.11-22   DOI: 10.12677/SSC.2014.21002  
  • 下载量: 1,986  浏览量: 8,535   国家自然科学基金支持


靳文静,韩 光,何心伟,胡 凯,商永嘉:安徽师范大学,化学与材料科学学院,功能分子固体教育部重点实验室,芜湖

异腈多组分反应组合化学杂环化合物Isocyanides Multicomponent Reactions Combinational Chemistry Heterocyclic Compounds



This paper reviewed the new progresses of the multicomponent reactions based on isocyanides to synthesize the heterocyclic compounds, and mainly introduced some new reactions of the Ugi multicomponent reactions. The request of substrates, reaction conditions, selectivity, yield and mechanism were investigated in detail. Meanwhile, a brief introduction of some new Passerini multicomponent reactions was given. New breakthroughs in this field were intensely expected.

靳文静, 韩光, 何心伟, 胡凯, 商永嘉. 异腈参与的多组分反应新进展[J]. 合成化学研究, 2014, 2(1): 11-22.


[1] [1] Dömling, A. (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chemical Reviews, 106, 17-89.
[2] Dömling, A. and Ugi, I. (2000) Multicomponent reactions with isocyanides. Angewandte Chemie International Edition, 39, 3168-3210.
[3] Majik, M.S., Parameswaran, P.S. and Tilve, S.G. (2009) Tandem Wittig-ene reaction approach to kainic acid. The Journal of Organic Chemistry, 74, 3591-3594.
[4] Gidlöf, R., Johansson, M. and Sterner, O. (2010) Tandem Pd-catalyzed carbonylation and intramolecular vinyl allene Diels-Alder reaction toward galiellalactone analogues. Organic Letters, 12, 5100-5103.
[5] Enders, D., Grondal, C. and Huttl, M.R.M. (2007) Asymmetric organocatalytic domino reactions. Angewandte Chemie International Edition, 46, 1570.
[6] Lang, S. (2013) Unravelling the labyrinth of palladium-catalysed reactions involving isocyanides. Chemical Society Reviews, 42, 4867-4880.
[7] Sapuppo, G., Wang, Q., Swinnen, D. and Zhu, J.-P. (2014) Copper-catalyzed three-component synthesis of 5-acetamidoimidazoles from carbodiimides, acyl chlorides and isocyanides. Organic Chemistry Frontiers, 1, 240-246.
[8] Alcaide, B., Almendros, P., Aragoncillo, C., Callejo, R. and Ruiz, M.P. (2013) Organocatalyzed three-component Ugi and Passerini reactions of 4-oxoazetidine-2-carbaldehydes and azetidine-2,3-diones. Application to the synthesis of γ-lactams and γ-lactones. The Journal of Organic Chemistry, 78, 10154-10165.
[9] Bachman, M., Mann, S.E. and Sheppard, T.D. (2012) Rapid synthesis of highly functionalised α-amino amides and medium ring lactones using multicomponent reactions of amino alcohols and isocyanides. Organic & Biomolecular Chemistry, 10, 162-170.
[10] Ugi, I., Meyr, R., Fetzer, U. and Steinbrckner, C. (1959) Versuche mit Isonitrilen. Angewandte Chemie, 71, 386.
[11] Passerini, M. and Gazz, Sopra gli isonitrili(I) (1921) Compostodel p-isonitril-azobenzolo con acetone ed acido acetico. Gazzetta chimica Italiana, 51, 126-129.
[12] Gedey, S., Eycken, J.V. and Fulop, F. (2002) Liquid-phase combinatorial synthesis of alicyclic-lactams via Ugi four-component reaction. Organic Letters, 11, 1967-1969.
[13] Borisov, R., Polyakov, A., Medvedeva, L., Khrustalev, V., Guranova, N. and Voskressensky, L. (2010) Concise approach toward tetrazolo[1,5-a] [1,4] benzodiazepines via a novel multicomponent isocyanide-based condensation. Organic Letters, 17, 3894-3897.
[14] Shaabani, A., Soleimani, E., Rezayan, A.H., Sarvay, A. and Khavasi, H.R. (2008) Novel isocyanide-based four-component reaction: A facile synthesis of fully substituted 3,4-dihydrocoumarin derivatives. Organic Letters, 12, 2581-2584.
[15] Shaabani, A,, Rezayan, A.H., Ghasemi, S. and Sarvary, A. (2009) A mild and efficient method for the synthesis of 2,5-dihydro-5-imino-2-methylfuran-3,4-dicarboxylates via an isocyanide-based multicomponent reaction. Tetrahedron Letters, 50, 1456-1458.
[16] Shaabani, A., Maleki, A. and Rad, J.M. (2007) A novel isocyanide-based three-component reaction: Synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives. The Journal of Organic Chemistry, 72, 6309-6311.
[17] Shaabani, A., Maleki, A., Mofakham, H. and Khavasi, H.R. (2008) Novel isocyanide-based three-component synthesis of 3,4-dihydroquinoxalin-2-amine derivatives. Journal of Combinatorial Chemistry, 10, 323-326.
[18] Shaabani, A., Maleki, A., Mofakham, H. and Khavasi, H.R. (2008) Novel isocyanide-based three-component one-pot synthesis of cyanophenylamino-acetamide derivatives. Journal of Combinatorial Chemistry, 10, 883-885.
[19] Laurent, E.K., Aurence, G. and Julie, O. (2007) New Ugi-smiles-metathesis strategy toward the synthesis of pyrimido azepines. The Journal of Organic Chemistry, 72, 5835-5838.
[20] Zhu, X., Xu, X.P., Sun, C., Wang, H.Y., Zhao, K. and Ji, S.J. (2010) Direct construction of imino-pyrrolidine-thione scaffold via isocyanide-based multicomponent reaction. Journal of Combinatorial Chemistry, 12, 822-828.
[21] Huang, X. and Xu, J.F. (2009) One-pot facile synthesis of substituted isoindolinones via an ugi four-component con-densation/diels-alder cycloaddition/deselenization-aromatization sequence. The Journal of Organic Chemistry, 74, 8859-8861.
[22] Aguiam, N.R., Castro, V.I., Ribeiro, A.I.F., Fernandes, R.D.V., Carvalho, C.M., Costa, S.P.G. and Pereira-Lima, S.M.M.A. (2013) α,α-dialkylglycines obtained by solid phase ugi reaction performed over isocyanide functionalized resins. Tetrahedron, 69, 9161-9165.
[23] Mercalli, V., Meneghetti, F. and Tron, G.C. (2013) Isocyanide-mediated multicomponent synthesis of c-oximinoamidines. Organic Letters, 15, 5902-5905.
[24] Li, M., Kong, W., Wen, L.R. and Liu, F.H. (2012) Facile isocyanide-based one-pot three-component regioselective synthesis of highly substituted pyridin-2(1H)-one derivatives at ambient temperature. Tetrahedron, 68, 4838-4845.
[25] Ghandi, M. and Zarezadeh, N. (2013) Three-component one-pot synthesis of quinolineefuran conjugates from acetylenedicarboxylate, isocyanide, and 2-chloroquinoline-3-carbaldehyde. Tetrahedron, 69, 8668-8674.
[26] Soleimani, E., Zainali, M., Ghasemi, N. and Notash, B. (2013) Isocyanide-based multicomponent reactions: Synthesis of 2-(1-(alkylcarbamoyl)-2,2-dicyanoethyl)-N-alkylbenzamide and 1,7-diazaspiro[4,4]nonane-2,4-dione derivatives. Tetrahedron, 69, 9832-9838.
[27] Klaim, L.E., Gizolme, M. and Grimaud, L. (2006) O-arylative Passerini reactions. Organic Letters, 22, 5021-5023.
[28] Soeta, T., Kojima, Y., Ukaji, Y. and Inomata, K. (2010) O-Silylative passerini reaction: A new one-pot synthesis of αsiloxyamides. Organic Letters, 19, 4341-4343.
[29] Yanai, H., Oguchi, T. and Taguchi, T. (2009) Direct alkylative passerini reaction of aldehydes, isocyanides, and free aliphatic alcohols catalyzed by indium(iii) triflate. The Journal of Organic Chemistry, 10, 3927-3929.
[30] Brioche, J., Masso, G. and Zhu, G. (2010) Passerini three-component reaction of alcohols under catalytic aerobic oxidative conditions. Organic Letters, 7, 1432-1435.
[31] Moliner, F.D., Crosignani, S., Banfi, L., Riva, R. and Basso, A. (2010) Synthesis of 5-carboxamide-oxazolines with a passerini zhu/staudinger aza wittig two-step protocol. Journal of Combinatorial Chemistry, 12, 613-616.
[32] Kreye, O., Toth, T. and Meirer, M.A.R. (2011) Introducing multicomponent reactions to polymer science: Passerini reactions of renewable monomers. Journal of the American Chemical Society, 133, 1790-1792.
[33] Massoudi, A., Amini, I., Ramazani, A. and Nasrabadi, F.Z. (2012) Three-component passerini-smiles coupling reaction of aldehydes and isocyanides with tropolone catalyzed by silica nanoparticles. Turkish Journal of Chemistry, 36, 537544.
[34] Beasley, B.O., Clarkson, G.J. and Shipman, M. (2012) Passerini reactions for the efficient synthesis of 3,3-di-substituted oxetanes. Tetrahedron, 53, 2951-2953.
[35] Esmaeili, A.A., Ghalandarabad, S.A. and Jannati, S. (2013) A novel and efficient synthesis of 3,3-disubstituted indol-2-ones via Passerini three-component reactions in the presence of 4 A molecular sieves. Tetrahedron, 54, 406-408.
[36] Soeta, T. and Ukaji, Y. (2014) Carboxylic acid free novel isocyanide-based reactions. The Chemical Record, 14, 101116.