Mannich condensations of activated cyclic enamines

References

• Erian, A. W. The Chemistry of Beta-Enaminonitriles as Versatile Reagents in Heterocyclic Synthesis. Chem. Rev. 1993, 93, 1991. doi:10.1021/cr00022a002
   Web of Science ®Google Scholar
• Vincze, Z.; Nemes, P.; Balázs, B.; Tóth, G.; Scheiber, P. Cerium(III)-Catalyzed Cyclizations with 1-Cyanomethylene Tetrahydroisoquinoline: Substituent Controlled Formation of Fused Pyrroles or Pyridines. Synlett. 2004, 6, 1023. doi:10.1055/s-2004-822904
   Web of Science ®Google Scholar
• Vincze, Z.; Mucsi, Z.; Scheiber, P.; Nemes, P. 1,6-Electrocyclization of 1-Azatriene Derivatives. Eur. J. Org. Chem. 2008, 1092. doi:10.1002/ejoc.200700913
   Web of Science ®Google Scholar
• Vincze, Z.; Nemes, P. Synthesis and Cyclizations of 1-Azapolyene Derivatives. Tetrahedron 2011, 67, 3380. doi:10.1016/j.tet.2011.03.058
   Web of Science ®Google Scholar
• Vincze, Z.; Nemes, P. A Novel Strategy for the Synthesis of 2,6-Diaryl-1,2-Dihydropyridines via 6π-Electrocyclization. Tetrahedron 2013, 69, 6269. doi:10.1016/j.tet.2013.05.013
   Web of Science ®Google Scholar
• Cheng, Y.; Huang, Z.-T.; Wang, M.-X. Heterocyclic Enamines: The Versatile Intermediates in the Synthesis of Heterocyclic Compounds and Natural Products. Curr. Org. Chem. 2004, 8, 325. doi:10.2174/1385272043485936
   Web of Science ®Google Scholar
• Liu, Y.; Yu, C.-Y.; Wang, M.-X. Synthesis of Fused Heterocycles Utilizing the Heterocyclic Enamine Protocol. Arkivoc 2003, (ii), 146.
   Web of Science ®Google Scholar
• Wang, M.-X.; Liu, Y.; Gao, H.-Y.; Zhang, Y.; Yu, C.-Y.; Huang, Z.-T.; Fleet, G. W. J. Ring-Chain Tautomerism in Organic Synthesis: Synthesis of Heterocyclic Enamines from a Novel and Practical Formal Ring Transformation Reaction of Lactones. J. Org. Chem. 2003, 68, 3281. doi:10.1021/jo026560t
   PubMed Web of Science ®Google Scholar
• Coates, R. M.; MacManus, P. A. Expeditious Synthesis of 2,3-Dihydro-1H-Pyrrolo[1,2-a]Indoles, Pyrroloindole Quinones, and Related Heterocycles via Nenitzescu-Type Condensation of Quinone Monoketals with Exocyclic Enamino Esters. J. Org. Chem. 1982, 47, 4822. doi:10.1021/jo00145a058
   Web of Science ®Google Scholar
• Robinson, R. S.; Dovey, M. C.; Gravestock, D. Silver-Catalyzed Hydroamination: Synthesis of N-Bridgehead Pyrroles, Incorporating a Protection-Deprotection Strategy for Preparation of Cyclic Secondary Vinylogous Carbamates. Eur. J. Org. Chem. 2005, 2005, 505. doi:10.1002/ejoc.200400598
   Web of Science ®Google Scholar
• Bartoli, G.; Cimarelli, C.; Dalpozzo, R.; Palmieri, G. A Versatile Route to β-Enamino Esters by Acylation of Lithium Enamines with Diethyl Carbonate or Benzyl Chloroformate. Tetrahedron 1995, 51, 8613. doi:10.1016/0040-4020(95)00476-O
   Web of Science ®Google Scholar
• Mahendar, B.; Mattapally, S.; Ravinder, M.; Bannerjee, S. K.; Rao, V. J. US Patent 0296530A1, 2014.
   Google Scholar
• Zhao, M.-X.; Wang, M.-X.; Huang, Z.-T. The Aza–Ene or the Michael Addition? Examination of an Unusual Substituent Effect on the Reaction of Heterocyclic Ketene Aminals with Ethyl Propiolate. Tetrahedron 2002, 58, 1309. doi:10.1016/S0040-4020(02)00002-9
   Web of Science ®Google Scholar
• Singh, R. K.; Jain, S.; Sinha, N.; Mehta, A.; Naqvi, F.; Anand, N. A General and Efficient Synthesis of 3,6-Diazabicyclo[3.2.1]Octanes. Tetrahedron 2006, 62, 4011. doi:10.1016/j.tet.2006.02.030
   Web of Science ®Google Scholar
• Han, L.; Feng, Y.; Luo, M.; Yuan, Z.; Shao, X.; Xu, X.; Li, Z. 2,2,2-Trifluoroethanol Activated One-Pot Mannich-like Reaction of β-Nitroenamines, Secondary Amines, and Aromatic Aldehydes. Tetrahedron Letters 2016, 57, 2727. doi:10.1016/j.tetlet.2016.05.023
   Web of Science ®Google Scholar
• Yildirim, M.; Çelikel, D. A Rapid Access to Novel and Diverse 3-Oxothiazolo[3,2-c]Pyrimidine-8-Carboxylates Using Multicomponent Mannich Cyclisation Reactions. Mol. Divers. 2015, 19, 1. doi:10.1007/s11030-014-9546-2
   PubMed Web of Science ®Google Scholar
• Hammouda, M.; Abou Zeid, Z. M.; Metwally, M. A. New simple and one-pot synthetic routes to polyfunctionally substituted imidazo[1,2-a]pyridines, pyrido[1,2-a]pyrimidines, pyrido[1,2-a]-1,3-diazepines and imidazo[1,2-a]pyrimidines. Chem. Heterocyclic Comp. 2005, 41, 1525. doi:10.1007/s10593-006-0031-4
   Google Scholar
• Pilipecz, M. V.; Scheiber, P.; Vincze, Z.; Varga, T. G.; Tóth, G.; Nemes, P. One-Pot Reactions of Nitroenamines with Anilines and Ethyl Glyoxylate. Tetrahedron 2014, 70, 4355. doi:10.1016/j.tet.2014.04.096
   Web of Science ®Google Scholar
• Shvidenko, K.; Nazarenko, K.; Shvidenko, T.; Vlasenko, Y.; Kostyuk, A. Synthesis of Thieno[3,4-b]Pyrrole Derivatives Based on the Reaction of 1-Methyl-2-Nitromethylenepyrrolidine with Isothiocyanates. Tetrahedron Lett. 2014, 55, 5639. doi:10.1016/j.tetlet.2014.08.019
   Web of Science ®Google Scholar
• Lou, Y.; Xu, Y.; Chai, Z.; Shao, X.; Zhao, G.; Li, Z. Organocatalytic Michael Addition of 2-Nitro Methylene Imidazolidines to α,β-Unsaturated Aldehydes: Concise Synthesis of Chiral Insecticide Paichongding. Tetrahedron 2015, 71, 6651. doi:10.1016/j.tet.2015.07.056
   Web of Science ®Google Scholar
• Yildirim, M.; Çelikel, D.; Dürüst, Y.; Knight, D. W.; Kariuki, B. M. A Rapid and Efficient Protocol for the Synthesis of Novel Nitrothiazolo[3,2-c]Pyrimidines via Microwave-Mediated Mannich Cyclisation. Tetrahedron 2014, 70, 2122. doi:10.1016/j.tet.2014.02.003
   Web of Science ®Google Scholar
• Altug, C.; Burnett, A. K.; Caner, E.; Dürüst, Y.; Elliott, M. C.; Glanville, R. P. J.; Guy, C.; Westwell, A. D. An Efficient One-Pot Multicomponent Approach to 5-Amino-7-Aryl-8-Nitrothiazolo[3,2-a]Pyridines. Tetrahedron 2011, 67, 9522. doi:10.1016/j.tet.2011.10.005
   Web of Science ®Google Scholar
• Pilipecz, M. V.; Mucsi, Z.; Nemes, P.; Scheiber, P. Chemistry of Nitroenamines. Synthesis of Pyrrolizine Derivatives. Heterocycles 2007, 71, 1919. doi:10.1016/S0040-4039(00)02357-1
   Web of Science ®Google Scholar
• Cheng, Y.; Yang, H.-B.; Huang, Z.-T.; Wang, M.-X. Annulation of Heterocyclic Secondary Enamines with Dicarboxylic Acid Dichlorides, an Unexpected Ring Size Effect. Tetrahedron Lett. 2001, 42, 1757. doi:10.1016/S0040-4039(00)02357-1
   Web of Science ®Google Scholar
• Pilipecz, M. V.; Varga, T. R.; Mucsi, Z.; Scheiber, P.; Nemes, P. [3+3] Cyclization Reactions of ß-Nitroenamines and ß-Enaminonitriles with α,ß-Unsaturated Carboxylic Acid Chlorides. Tetrahedron 2008, 64, 5545–5550. doi:10.1016/j.tet.2008.03.090
   Web of Science ®Google Scholar
• Altuğ, C.; Dürüst, Y.; Elliott, M. C. Reactions of Alkylidenepyrrolidines with α-Chlorooximes and α-Chlorohydrazones. Tetrahedron Lett. 2009, 50, 7392. doi:10.1016/j.tetlet.2009.10.086
   Web of Science ®Google Scholar
• Altuğ, C.; Dürüst, Y.; Elliott, M. C.; Kariuki, B. M.; Rorstad, T.; Zaal, M. Reaction of Heterocyclic Enamines with Nitrile Oxide and Nitrilimine precursors. Org. Biomol. Chem. 2010, 8, 4978. doi:10.1039/c0ob00286k
   PubMed Web of Science ®Google Scholar
• Kondacs, L. A.; Pilipecz, M. V.; Mucsi, Z.; Balázs, B.; Gáti, T.; Nyerges, M.; Dancsó, A.; Nemes, P. Synthesis of Isoxazoline Derivatives Based on Nitrile Oxide Cycloaddition of Nitroso-Nitro-Enamine. Eur. J. Org. Chem. 2015, 6872. doi:10.1002/ejoc.201500905
   Web of Science ®Google Scholar
• Tanino, H.; Nakata, T.; Kaneko, T.; Kishi, Y. A Stereospecific Total Synthesis of d,l-saxitoxin. J. Am. Chem. Soc. 1977, 99, 2818. doi:10.1021/ja00450a079
   PubMed Web of Science ®Google Scholar
• Hong, C. Y.; Kishi, Y. Enantioselective Total Synthesis of (-)-Decarbamoylsaxitoxin. J. Am. Chem. Soc. 1992, 114, 7001. doi:10.1021/ja00044a008
   Web of Science ®Google Scholar
• Vincze, Z.; Pilipecz, M. V.; Scheiber, P.; Varga, T. R.; Tóth, G.; Nemes, P. Simple Route to Multisubstituted Tetrahydropyrimidines. Tetrahedron 2015, 71, 6135. doi:10.1016/j.tet.2015.06.100
   Web of Science ®Google Scholar
• Kappe, C. O. Biologically Active Dihydropyrimidones of the Biginelli-Type – A Literature Survey. Eur. J. Med. Chem. 2000, 35, 1043. doi:10.1016/S0223-5234(00)01189-2
   PubMed Web of Science ®Google Scholar
• Haggarty, S. J.; Mayer, T. U.; Miyamoto, D. T.; Fathi, R.; King, R. W.; Mitchison, T. J.; Schreiber, S. L. Dissecting Cellular Processes Using Small Molecules: Identification of Colchicine-Like, Taxol-Like and Other Small Molecules That Perturb mitosis. Chem. Biol. 2000, 7, 275. doi:10.1016/S1074-5521(00)00101-0
   PubMed Web of Science ®Google Scholar
• Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. Small Molecule Inhibitor of Mitotic Spindle Bipolarity Identified in a Phenotype-Based Screen. Science 1999, 286, 971. doi:10.1126/science.286.5441.971
   PubMed Web of Science ®Google Scholar
• Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwartz, J.; Malley, M. F. Dihydropyrimidine Calcium Channel Blockers. 4. Basic 3-Substituted-4-Aryl-1,4-dihydropyrimidine-5-carboxylic Acid Esters. Potent Antihypertensive Agents. J. Med. Chem. 1992, 35, 3254. doi:10.1021/jm00095a023
   PubMed Web of Science ®Google Scholar
• Messer, W. S.; Abuh, Y. F.; Liu, Y.; Periyasamy, S.; Ngur, D. O.; Edgar, M. A. N.; El-Assadi, A. A.; Sbeih, S.; Dunbar, P. G.; Roknich, S.; et al. Synthesis and Biological Characterization of 1,4,5,6-Tetrahydropyrimidine and 2-Amino-3,4,5,6-tetrahydropyridine Derivatives as Selective m1 Agonists. J. Med. Chem. 1997, 40, 1230. doi:10.1021/jm960467d
   PubMed Web of Science ®Google Scholar
• Nair, V.; Chi, G.; Ptak, R.; Neamati, N. HIV Integrase Inhibitors with Nucleobase Scaffolds: Discovery of a Highly Potent Anti-HIV Agent. J. Med. Chem. 2006, 49, 445. doi:10.1021/jm0508890
   PubMed Web of Science ®Google Scholar
• Zhou, S.; Kern, E. R.; Gullen, E.; Cheng, Y. C.; Drach, J. C.; Matsumi, S.; Mitsuya, H.; Zemlicka, J. (Z)- and (E)-[2-Fluoro-2-(Hydroxymethyl)Cyclopropylidene]Methylpurines and -Pyrimidines, a New Class of Methylenecyclopropane Analogues of Nucleosides: Synthesis and Antiviral Activity 1. J. Med. Chem. 2004, 47, 6964. doi:10.1021/jm040093l
   PubMed Web of Science ®Google Scholar
• Bahekar, S. S.; Shinde, D. B. Synthesis and Anti-inflammatory Activity of Some [4,6-(4-substituted aryl)-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-Acetic acid Derivatives. Bioorg. Med. Chem. Lett. 2004, 14, 1733. doi:10.1016/j.bmcl.2004.01.039
   PubMed Web of Science ®Google Scholar
• Scheiber, P.; Tóth, G.; Pilipecz, M. V.; Varga, T. G.; Nemes, P. Chemistry of Nitroenamines. Part 2. Synthesis of Saturated Pyrrolo-Pyrimidines and -Pyrazines. Heterocycles 2011, 83, 2001. doi:10.3987/COM-11-12246
   Web of Science ®Google Scholar
• Bahaji, E. H.; Tronche, P.; Couquelet, J.; Harraga, S.; Panouse-Perrin, J.; Rubat, C. Studies on Immunostimulating Derivatives: Synthesis of Some pyrrolo[1,2-c]pyrimidines. Chem. Pharm. Bull. 1991, 39, 2126. doi:10.1248/cpb.39.2126
   PubMed Web of Science ®Google Scholar
• Katritzky, A. R.; Rachwal, S.; Hitchings, G. J. Benzotriazole: A novel synthetic auxiliary. Tetrahedron 1991, 47, 2683. doi:10.1016/S0040-4020(01)87080-0
   Web of Science ®Google Scholar
• Katritzky, A. R.; Rachwal, S.; Rachwal, B. The Chemistry of Benzotriazole. Part 3. The Aminoalkylation of Benzotriazole. J. Chem. Soc. Perkin Trans. 1987, 1, 799. doi:10.1039/p19870000799
   Google Scholar
• Katritzky, A. R.; Ürögdi, L.; Mayence, A. The Chemistry of N-Substituted Benzotriazoles Part 23. Synthesis of Tertiary α-Amino Esters. Synthesis 1989, 323. doi:10.1055/s-1989-27244
   Web of Science ®Google Scholar