K₂CO₃/Al₂O₃: An efficient and recyclable catalyst under solvent free conditions for the reaction of electron-deficient nitro-olefins with 1,3-dicarbonyl compounds

References

• Berner, O.M.; Tedeschi, L.; Enders, D. Asymmetric Michael Additions to Nitroalkenes. Eur. J. Org. Chem. 1877, 2002. doi:10.1002/1099-0690(200206)2002;
   Google Scholar
  (b) Ono, N. Nitro Group in Organic Synthesis; Wiley-VCH, New York, NY, 2001;
   Google Scholar
  (c) Okino, T.; Hoashi, Y.; Takemoto, Y. Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts. J. Am. Chem. Soc. 2003, 125, 12672–12673. doi:10.1021/ja036972z.
   PubMed Web of Science ®Google Scholar
• (a) Winn, M.; von Geldern, T.W.; Opgenorth, T.J.; Jae, H.-S.; Tasker, A.S.; Boyd, S.A.; Kester, J.A.; Mantei, R.A.; Bal, R.; Sorensen, B.K.; et al. 2,4-Diarylpyrrolidine-3- Carboxylic AcidsPotent ETA Selective Endothelin Receptor Antagonists. 1. Discovery of a-127722. J. Med. Chem. 1996, 39, 1039–1048. doi:10.1021/jm9505369;
   PubMed Web of Science ®Google Scholar
  (b) Wu- Wong, J.R.; Dixon, D.B.; Chiou, W.J.; Dayton, B.D.; Novosad, E.I.; Adler, A.L.; Wessale, J.L.; Calzadilla, S.V.; Hernandez, L.; Marsh, K.C.; et al. Pharmacology of a- 216546: A Highly Selective Antagonist for Endothelin ETA Receptor. Eur. J. Pharmacol. 1999, 366, 189–201;
   PubMed Web of Science ®Google Scholar
  (c) Barnes, D.M.; Ji, J.; Fickes, M.G.; Fitzgerald, M.A.; King, S.A.; Morton, H.E.; Plagge, F.A.; Preskill, M.; Wagaw, S.H.; Wittenberger, S.J.; et al. Development of a Catalytic Enantioselective Conjugate Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes for the Synthesis of Endothelin-a Antagonist ABT-546. Scope, Mechanism, and Further Application to the Synthesis of the Antidepressant Rolipram. J. Am. Chem. Soc. 2002, 124, 13097–13105. doi:10.1021/ja026788y.
   PubMed Web of Science ®Google Scholar
• (a) Pinnick, H.W. The Nef Reaction. Org. React. 1990, 38, 655–792. doi:10.1002/0471264180.or038.03;
   Web of Science ®Google Scholar
  (b) Tamura, R.; Kamimura, A.; Ono, N. Displacement of Aliphatic Nitro Groups by Carbon and Heteroatom Nucleophiles. Synthesis 1991, 423–434. doi:10.1055/s-1991-26484;
   Web of Science ®Google Scholar
  (c) Mukayama, T.; Hoshino, T. The Reactions of Primary Nitro- Paraffins with Isocyanates. J. Am. Chem. Soc. 1960, 82, 5339–5342. doi:10.1021/ja01505a017.
   Web of Science ®Google Scholar
• (a) Jung, M.E. In Comprehensive Organic Synthesis, Trost, B.M., Fleming, I., Eds.; Pergamon: Oxford, 1991, 4, pp 1–67;
   Google Scholar
  (b) Nelson, J.H.; Howells, P.N.; DeLullo, G.C.; Landen, G.L. Nickel-Catalyzed Michael Additions of β- Dicarbonyls. J. Org. Chem. 1980, 45, 1246–1249.
   Web of Science ®Google Scholar
• Saidi, M.R.; Azizi, N.; Akbari, E.; Ebrahimi, F. LiClO4/Et3N: Highly Efficient and Active Catalyst for Selective Michael Addition Ofactive Methyleneb compounds under Solvent-Free Condition. J. Mol. Cat. a: Chem. 2008, 292, 44–48. doi:10.1016/j.molcata.2008.06.003.
   Google Scholar
• Yang, W.; Luo, S.; Yu, C.; Wang, B.; Yue, H.; Wang, L.; Xu, D. Base-Catalyzed Michael Reaction of Malonate with Α, β-Unsaturated Compounds in Ionic Liquids. Huaxue Yanjiu Yu Yingyong 2006, 18, 537–541.
   Google Scholar
• Annamalai, V.; DiMauro, E.F.; Carroll, P.J.; Kozlowski, M.C. Catalysis of the Michael Addition Reaction by Late Transition Metal Complexes of BINOL-Derived Salens. J. Org. Chem. 2003, 68, 1973–1981. doi:10.1021/jo025993t.
   PubMed Web of Science ®Google Scholar
• Corey, E.J.; Zhang, F.-Y. Enantioselective Michael Addition of Nitromethane to Α, β- Enones Catalyzed by Chiral Quaternary Ammonium Salts. A Simple Synthesis of (R)- Baclofen. Org. Lett. 2000, 2, 4257–4259. doi:10.1021/ol0068344.
   PubMed Web of Science ®Google Scholar
• Hanessian, S.; Pham, V. Catalytic Asymmetric Conjugate Addition of Nitroalkanes to Cycloalkenones. Org. Lett. 2000, 2, 2975–2978. doi:10.1021/ol000170g.
   PubMed Web of Science ®Google Scholar
• Li, H.; Wang, Y.; Tang, L.; Deng, L. Highly Enantioselective Conjugate Addition of Malonate and β-Ketoester to Nitroalkenes: Asymmetric C-C Bond Formation with New Bifunctional Organic Catalysts Based on Cinchona Alkaloids. J. Am. Chem. Soc. 2004, 126, 9906–9907. doi:10.1021/ja047281l.
   PubMed Web of Science ®Google Scholar
• Halland, N.; Aburel, P.S.; Jorgensen, K.A. Highly Enantioselective Organocatalytic Conjugate Addition of Malonates to Acyclic Alpha, Beta-Unsaturated Enones. Angew. Chem., Int. Ed. 2003, 42, 661–665. doi:10.1002/anie.200390182.
   PubMed Web of Science ®Google Scholar
• Ballini, R.; Rinaldi, A. Michael Addition of Nitroalkanes to Dimethyl Maleate with DBU. a New Direct Method for the Synthesis of Polyfunctionalized Α, β–Unsaturated Esters. Tetrahedron Lett. 1994, 35, 9247–9250.10.1016/0040-4039(94)88479-X
   Web of Science ®Google Scholar
• (a) Weiping, Y.; Junye, X.; Chin-Tong, T.; Choon-Hong, T. 1,5,7-Triazabicyclo[4.4.0] Dec-5-Ene (TBD) Catalyzed Michael Reactions. Tetrahedron Lett. 2005, 46, 6875–6878. doi:10.1016/j.tetlet.2005.08.010;
   Web of Science ®Google Scholar
  (b) Tu, Z.; Jang, Y.; Lin, C.; Liu, J.T.; Hsu, J.; Sastry, M.N.V.; Yao, C.-F. The Study of Reaction Mechanism for the Transformation of Nitronate into Nitrile by Phosphorus Trichloride. Tetrahedron 2005, 61, 10541–10551. doi:10.1016/j.tet.2005.08.041.
   Web of Science ®Google Scholar
• Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. Enantio- and Diastereo- Selective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea. J. Am. Chem. Soc. 2005, 127, 119–125. doi:10.1021/ja044370p.
   PubMed Web of Science ®Google Scholar
• Chen, F.-X.; Shao, C.; Wang, Q.; Gong, P.; Zhang, D.-Y.; Zhanga, B.-Z.; Wanga, R. An Enantioselective Michael Addition of Malonate to Nitroalkenes Catalyzed by Low Loading Demethylquinine Salts in Water. Tetrahedron. Lett. 2007, 48, 8456–8459. doi:10.1016/j.tetlet.2007.09.168.
   Web of Science ®Google Scholar
• Evans, D.A.; Mito, S.; Seidel, D. Scope and Mechanism of Enantioselective Michael Additions of 1,3-Dicarbonyl Compounds to Nitroalkenes Catalyzed by Nickel(II)- Diamine Complexes. J. Am. Chem. Soc. 2007, 129, 11583–11592. doi:10.1021/ja0735913.
   PubMed Web of Science ®Google Scholar
• (a) Clark, J.H.; Rhodes, C.N. Clean Synthesis Using Porous Inorganic Solid Catalysts and Supported Reagents; Royal Society of Chemistry, Cambridge, 2000;
   Google Scholar
  (b) Gerard, V.S.; Notheisz, F. Heterogeneous Catalysis in Organic Chemistry; Elsevier, San Diego, 2000;
   Google Scholar
  (c) Rafiee, E.; Rashidzadeh, S.; Azada, A. Silica-Supported Heteropoly Acids: Highly Efficient Catalysts for Synthesis of Α-Aminonitriles, Using Trimethylsilyl Cyanide or Potassium Cyanide. J. Mol. Catal. A: Chem. 2007, 261, 49–52. doi:10.1016/j.molcata.2006.07.058;
   Google Scholar
  (d) Davoodnia, A.; Bakavoli, M.; Barakouhi, G.; Tavakoli-Hoseini, N. A New Route to the Synthesis of Thieno[2,3-D]Pyrimidin-4(3H)-One Derivatives Catalyzed by 12-Tungstophosphoric Acid (H3PW12O40). Chin. Chem. Lett. 2007, 18, 1483–1486. doi:10.1016/j.cclet.2007.10.013;
   Web of Science ®Google Scholar
  (e) Tavakoli-Hoseini, N.; Davoodnia, A. Silica Gel-Supported Polyphosphoric Acid: A Mild, Efficient and Reusable Catalyst for the One-Pot Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles. Asian J. Chem. 2010, 22, 7197–7200;
   Web of Science ®Google Scholar
  (f) Davoodnia, A.; Tavakoli-Nishaburi, A.; Tavakoli-Hoseini, N. Carbon- Based Solid Acid Catalyzed One-Pot Mannich Reaction: A Facile Synthesis of β-Amino Carbonyl Compounds. Bull. Korean Chem. Soc. 2011, 32, 635–638. doi:10.5012/bkcs.2011.32.2.63.
   Web of Science ®Google Scholar
• (a) Corma, A.; Garcia, H. Silica-Bound Homogenous Catalysts as Recoverable and Reusable Catalysts in Organic Synthesis. Adv. Synth. Catal. 2006, 348, 1391–1412;
   Web of Science ®Google Scholar
  (b) Niknam, K.; Karimi, B.; Zolfigol, M.A. Silica Sulfuric Acid Promoted Aromatization of 1,2-Dihydroquinolines by Using NaNO2 Asoxidizing Agent under Mild and Heterogeneous Conditions. Catal. Commun. 2007, 8, 1427–1430;
   Web of Science ®Google Scholar
  (c) Niknam, K.; Zolfigol, M.A.; Khorramabadi-Zad, A.; Zare, R.; Sheygan, M. Silica Sulfuric Acid as an Efficient and Recyclable Catalyst for the Methoxymethylation of Alcohols under Solvent-Free Conditions. Catal. Commun. 2006, 7, 494–498;
   Web of Science ®Google Scholar
  (d) Kozhevinkov, I.V. In Catalysis by Poly Oxometalates; Wiley, Chichester, 2002; pp 2–22;
   Google Scholar
  (e) Hajipour, A.R.; Ruoho, A.E. Nitric Acid in the Presence of P2O5supported on Silica Gel – A Useful Reagent for Nitration of Aromatic Compounds under Solvent-Free Conditions. Tetrahedron Lett. 2005, 46, 8307–8310. doi:10.1016/j.tetlet.2005.09.178;
   Web of Science ®Google Scholar
  (f) Kantevari, S.; Bantu, R.; Nagarapu, L. HClO4–SiO2 and PPA–SiO2 Catalyzed Efficient One-Pot Knoevenagel Condensation, Michael Addition and Cyclo-Dehydration of Dimedone and Aldehydes in Acetonitrile, Aqueous and Solvent Free Conditions: Scope and Limitations. J. Mol. Catal. a: Chem. 2007, 269, 53–57. doi:10.1016/j.molcata.2006.12.039;
   Web of Science ®Google Scholar
  (g) Davoodnia, A.; Roshani, M.; Malaeke, S.H.; Bakavoli, M. A Rapid Synthesis of Isoxazolo[5,4-D]Pyrimidin-4(5H)-Ones under Microwave Irradiation with Solid Acid Catalysis in Solvent-Free Conditions. Chin. Chem. Lett. 2008, 19, 525–528. doi:10.1016/j.cclet.2008.01.037.
   Web of Science ®Google Scholar
• (a) Khan, A.T.; Ghosh, S.; Choudhury, L.H. Perchloric Acid Impregnated on Silica Gel (HClO4/SiO2): a Versatile Catalyst for Michael Addition of Thiols to the Electron Deficient Alkenes. Eur. J. Org. Chem. 2006, 9, 2226–2231. doi:10.1002/ejoc.200600006;
   Web of Science ®Google Scholar
  (b) Zeinali-Dastmalbaf, M.; Davoodnia, A.; Heravi, M.M.; Tavakoli-Hoseini, N.; Khojastehnezhad, A.; Zamani, H.A. Silica Gel-Supported Polyphosphoric Acid (PPA- SiO2) Catalyzed One-Pot Multi-Component Synthesis of 3,4-Dihydropyrimidin-2(1H)- Ones and -Thiones: An Efficient Method for the Biginelli Reaction. Bull. Korean Chem. Soc. 2011, 32, 656–658. doi:10.5012/bkcs.2011.32.2.656;
   Web of Science ®Google Scholar
  (c) Khojastehnezhad, A.; Davoodnia, A.; Bakavoli, M.; Tavakoli- Hoseini, N.; Zeinali-Dastmalbaf, M. Silica Gel- Supported Polyphosphoric Acid (PPA/SiO2): an Efficient and Reusable Heterogeneous Catalyst for Facile Synthesis of 14-Aryl-14H-Dibenzo[a]Xanthenes under Solvent-Free Conditions. Chin. J. Chem. 2011, 29, 297–302. doi:10.1002/cjoc.201190081;
   Web of Science ®Google Scholar
  (d) Li, H.; Yua, X.; Tua, S.T.; Yanb, J.; Wanga, Z. Catalytic Performance and Characterization of Al2O3-Supported Pt–Co Catalyst Coatings for Preferential CO Oxidation in a Micro- Reactor. Appl. Catal. A 2010, 387, 215–223. doi:10.1016/j.apcata.2010.08.030;
   Web of Science ®Google Scholar
  (e) Emrani, A.; Davoodnia, A.; Tavakoli-Hoseini, N. Alumina Supported Ammonium Dihydrogenphosphate (NH4H2PO4/Al2O3): Preparation, Characterization and Its Application as Catalyst in the Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles. Bull. Korean Chem. Soc. 2011, 32, 2385–2390. doi:10.5012/bkcs.2011.32.7.2385.
   Web of Science ®Google Scholar
• Davoodnia, A.; Khojastehnezhad, A.; Tavakoli-Hoseini, N. Carbon-Based Solid Acid as an Efficient and Reusable Catalyst for the Synthesis of 1,8-Dioxodecahydroacridines under Solvent-Free Conditions. Bull. Korean Chem. Soc. 2011, 32, 2243–2248. doi:10.5012/bkcs.2011.32.7.2243.
   Web of Science ®Google Scholar
• Tanaka, K.; Toda, F. Solvent-Free Organic Synthesis. Chem. Rev. 2000, 100, 1025–1074. doi:10.1021/cr940089p.
   PubMed Web of Science ®Google Scholar
• (a) Shumaila, A.M.A.; Kusurkar, R.S. Silica Gel, an Effective Catalyst for the Reaction of Electron-Deficient Nitro-Olefins with Nitrogen Heterocycles. Synth. Commun. 2010, 40, 2935–2940. doi:10.1080/00397910903340694;
   Web of Science ®Google Scholar
  (b) Shumaila, A.M.A.; Puranik, V.G.; Kusurkar, R.S. Diastereoselective Synthesis of Tetrasubstituted-Octahydro-3,6- Diazacarbazoles and Tetrasubstituted-3,6-Diazacarbazoles via Double Pictet-Spengler Reaction. Tetrahedron Lett. 2011, 52, 2661–2663. doi:10.1016/j.tetlet.2011.03.060;
   Web of Science ®Google Scholar
  (c) Shumaila, A.M.A.; Puranik, V.G.; Kusurkar, R.S. Synthesis of Tetrahydro-5-Azaindoles and 5-Azaindoles Using PicteteSpengler Reactiondappreciable Difference in Products Using Different Acid Catalysts. Tetrahedron 2011, 67, 936–942. doi:10.1016/j.tet.2010.12.003;
   Web of Science ®Google Scholar
  (d) Dattatray, G.H.; Shumaila, A.M.A.; Kusurkar, R.S. Silica Gel-Supported Bismuth Nitrate Pentahydrate:A Highly Active Catalyst under Solvent Free Conditions towards the Synthesis of Dihydropyrimidin-2(1H)-Ones and Their Sulphur Analogues. Indian J. Chem., Sec B 2013, 52, 1161–1165.
   Google Scholar
• The catalyst (KCA) was prepared with the help of Procedure reported by: Yamaguchi, T.; Zhu, J.-H.; Wang, Y.; Komatsu, M.-A.; Ookawa, M. Supported K-Salts as a New Solid Base Catalyst. Chem. Lett. 1997, 989–990. doi:10.1246/cl.1997.989.
   Web of Science ®Google Scholar