Addition-elimination of nitroalkanes to 3-phenacylideneoxindoles—direct method for the synthesis of 3-alkenylphenacylidene-oxindoles

References

• Majik, M. S.; Rodrigues, C.; Mascarenhas, S.; D’Souza, L. Design and Synthesis of Marine Natural Product-Based 1H-Indole-2,3-Dionescaffold as a New Antifouling/Antibacterial Agent against Fouling Bacteria. Bioorg. Chem. 2014, 54, 89-95. DOI: 10.1016/j.bioorg.2014.05.001.
   PubMed Web of Science ®Google Scholar
• Singh, D.; Fatma, S.; Ankit, P.; Mishra, P.; Singh, S.; Singh, S. B.; Singh, J. Microwave-Induced Solvent-Free Synthesis and Antifungal Screening of Novel Spiro Heterocyclic Systems Containing 3,5-Diphenyl-7H-Thiazolo[3,2-a]Pyrimidine and Indolin-2-One. Synth. Commun. 2013, 43, 3072-3082. DOI: 10.1080/00397911.2013.769604.
   Web of Science ®Google Scholar
• Singh, G. S.; Desta, Z. Y. Isatins as Privileged Molecules in Design and Synthesis of Spiro-Fused Cyclic Frameworks. Chem. Rev. 2012, 112, 6104-6155. DOI: 10.1021/cr300135y.
   PubMed Web of Science ®Google Scholar
• Sebahar, P. R.; Williams, R. M. The Asymmetric Total Synthesis of (+)- and (−)-Spirotryprostatin B. J. Am. Chem. Soc. 2000, 122, 5666-5667. DOI: 10.1021/ja001133n.
   Web of Science ®Google Scholar
• Reddy, B. V. S.; Rajeswari, N.; Sarangapani, M.; Roopa Reddy, G.; Madan, C.; Pranay Kumar, K.; Srinivasa Rao, M. Iodine-Catalyzed Conjugate Addition of Indoles onto En-1,4-Dione: A Novel Synthesis of 3-(1-(1H-Indol-3-yl)-2-Oxo-2-Phenylethyl)Indolin-2-Ones as Antibacterial and Antifungal Agents. Bioorg. Med. Chem. Lett. 2011, 21, 6510-6514. DOI: 10.1016/j.bmcl.2011.08.075.
   PubMed Web of Science ®Google Scholar
• Liu, Y. Y.; Wang, H.; Wan, J. P. Recent Advances in Diversity Oriented Synthesis through Isatin-Based Multicomponent Reactions. Asian J. Org. Chem. 2013, 2, 374-386. DOI: 10.1002/ajoc.201200180.
   Web of Science ®Google Scholar
• Cao, Z. Y.; Wang, Y. H.; Zeng, X. P.; Zhou, J. Catalytic Asymmetric Synthesis of 3,3-Disubstituted Oxindoles: Diazooxindole Joins the Field. Tetrahedron Lett. 2014, 55, 2571-2584. DOI: 10.1016/j.tetlet.2014.01.084.
   Web of Science ®Google Scholar
• Yang, W.; Du, D. M. Cinchona-Based Squaramide-Catalyzed Cascade aza-Michael-Michael Addition: Enantioselective Construction of Functionalized Spirooxindole Tetrahydroquinolines. Chem. Commun. 2013, 49, 8842-8844. DOI: 10.1039/c3cc44930k.
   PubMed Web of Science ®Google Scholar
• Gnanamani, S.; Perumal, P. T. InCl3-Catalyzed Efficient One-Pot Synthesis of 2-Pyrrolo-3′-Yloxindoles. Tetrahedron Lett. 2009, 50, 3959-3962. DOI: 10.1016/j.tetlet.2009.04.089.
   Google Scholar
• Cai, Y. F.; Liu, X. H.; Zhou, P. F.; Kuang, Y. L.; Lin, L. L.; Feng, X. M. Iron-Catalyzed Asymmetric Haloamination Reactions. Chem. Commun. 2013, 49, 8054-8056. DOI: 10.1039/c3cc44421j.
   PubMed Web of Science ®Google Scholar
• Tan, B.; Candeias, N. R.; Barbas, C. F. Construction of Bispirooxindoles Containing Three Quaternary Stereocentres in a Cascade Using a Single Multifunctional Organocatalyst. Nature Chem. 2011, 3, 473-477. DOI: 10.1038/nchem.1039.
   PubMed Web of Science ®Google Scholar
• Zhou, R.; Yang, C. J.; Liu, Y. Y.; Li, R. F.; He, Z. J. Diastereoselective Synthesis of Functionalized Spirocyclopropyl Oxindoles via P(NMe2)3-Mediated Reductive Cyclopropanation. J. Org. Chem. 2015, 46, 10709-10715. DOI: 10.1021/jo502106c.
   Google Scholar
• Albertshofer, K.; Tan, B.; Barbas, C. F. Assembly of Spirooxindole Derivatives Containing Four Consecutive Stereocenters via Organocatalytic Michaelhenry Cascade Reactions. Org. Lett. 2012, 14, 1834-1837. DOI: 10.1021/ol300441z.
   PubMed Web of Science ®Google Scholar
• Zhou, J.; Wang, Q. L.; Peng, L.; Tian, F.; Xu, X. Y.; Wang, L. X. An Organocatalytic Domino Michael-Alkylation Reaction: Highly Enantioselective Construction of Spiro-Cyclopentanoneoxindoles and Tetronic Acid Scaffolds. Chem. Commun. 2014, 50, 14601-14604. DOI: 10.1039/C4CC05207B.
   PubMed Web of Science ®Google Scholar
• Sun, Q. S.; Chen, X. Y.; Zhu, H.; Lin, H.; Sun, X. W.; Lin, G. Q. Asymmetric Synthesis of Poly-Substituted Spirocyclohexane Oxindole via a Squaramide Catalyzed Cascade Michael-Michael-Aldol Sequence. Org. Chem. Front. 2015, 2, 110-113. DOI: 10.1039/C4QO00299G.
   Web of Science ®Google Scholar
• Higashiyama, K.; Nagase, H.; Yamaguchi, R.; Kawai, K.; Otomasu, H. Michael Reactions of 3-Acylmethyleneoxindoles with Active Methylene Compounds. Chem. Pharm. Bull. 1985, 33, 544-550. DOI: 10.1248/cpb.33.544.
   Web of Science ®Google Scholar
• Lu, L. J.; Fu, Q.; Sun, J.; Yan, C. G. Synthesis of Complex DispirocyclopEntanebisoxindoles via Cycloaddition Reactions of 4-Dimethylamino-1-Alkoxycarbonylmethylpyridinium Bromides with 2-Oxoindolin-3-Ylidene Derivatives. Tetrahedron 2014, 70, 2537-2545. DOI: 10.1016/j.tet.2014.02.050.
   Web of Science ®Google Scholar
• Fu, Q.; Yan, C. G. Molecular Diversity of Cycloaddition Reactions of the Functionalized Pyridinium Salts with 3-Phenacylideneoxindoles. Tetrahedron 2013, 69, 5841-5849. DOI: 10.1016/j.tet.2013.05.034.
   Web of Science ®Google Scholar
• Lu, L. J.; Yan, C. G. Synthesis of Dispirocyclopentyl-3,3'-Bisoxindoles via Base Promoted Cyclization Reaction of 3-Phenacylideneoxindoles with Nitromethane. Tetrahedron 2014, 70, 9587-9591. DOI: 10.1016/j.tet.2014.11.028.
   Web of Science ®Google Scholar
• Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petrini, M. Conjugate Additions of Nitroalkanes to Electron-Poor Alkenes: Recent Results. Cheminform 2005, 36, 933-971. DOI: 10.1002/chin.200526257.
   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. DOI: 10.1002/chin.199518077.
   Web of Science ®Google Scholar
• Ballini, R.; Palmieri, A. Potassium Fluoride/Basic Alumina as Far Superior Heterogeneous Catalyst for the Chemoselective Conjugate Addition of Nitroalkanes to Electron-Poor Alkenes Having Two Electron-Withdrawing Groups in α- and β-Positions. Adv. Synth. Catal. 2006, 348, 1154-1156. DOI: 10.1002/adsc.200606105.
   Web of Science ®Google Scholar
• Ballini, R.; Bosica, G.; Damiani, M.; Righi, P. Nitroalkanes as a New Source of 2-Alkylidene-1,4-Diols, in Two Steps. Tetrahedron 1999, 55, 13451-13456. DOI: 10.1016/S0040-4020(99)00829-7.
   Web of Science ®Google Scholar
• Ballini, R.; Marcantoni, E.; Perella, S. A Two Steps Synthesis of γ-Substituted and γ,γ-Disubstituted α-(Alkylmethylene)-γ-Butyrolactones. J. Org. Chem. 1999, 64, 2954-2957. DOI: 10.1021/jo982131c.
   PubMed Web of Science ®Google Scholar
• Ballini, R.; Bosica, G.; Mase, A.; Petrini, M. Synthesis of (E)-3-Alkylidenepyrrolidines by Nucleophilic Ring Closure of (E)-2-Alkylidene-1,4-Diol Derivatives. Eur. J. Org. Chem. 2000, 2000, 2927-2931. DOI: 10.1002/1099-0690(200008)2000:16 < 2927:aid-ejoc2927 > 3.0.co;2-y.
   Web of Science ®Google Scholar
• Ballini, R.; Bosica, G.; Palmieri, A.; Petrini, M.; Pierantozzi, C. Conjugate Addition of Nitroalkanes to Dimethyl Maleate. Regioselective Formation of Both Monoesters of 2-Alkylsuccinic Acids. Tetrahedron 2003, 59, 7283-7289. DOI: 10.1016/s0040-4020(03)01175-x.
   Web of Science ®Google Scholar