Efficient methods for microwave assisted regioselective aminations of 3,6-dichloropyridazines: novel synthesis of (E)-2-(3,6-dichloropyridazin-4-yl)vinyl-amines

References

• (a) Tisler, M.; Stanovnik, B. In Comprehensive Heterocyclic Chemistry I. (ed. by; Rees, C. W.; Katritzky, A. R.) Pergamon: Oxford, UK, 1984; pp 1–56.
   Google Scholar
  (b) Coates, W. J. In Comprehensive Heterocyclic Chemistry II. Vol 6. (ed. Scriven, E.F.V., Rees, C.W.; Katritzky, A.R.) Pergamon: Oxford, UK, 1996; pp 1–91.
   Google Scholar
• (a) Brown, D. J. In Comprehensive Heterocyclic Chemistry I. (ed. by.; Rees, C. W.; Katritzky, A. R.) Pergamon: Oxford, UK, 1984; pp 57–155.
   Google Scholar
  (b) Undheim, K.; Benneche, T. In Comprehensive Heterocyclic Chemistry II. Vol 6. (ed. Scriven, E.F.V., Rees, C.W.; Katritzky, A.R.) Pergamon: Oxford, UK, 1996; pp 93–231.
   Google Scholar
• (a) Porter, A. E. A. In Comprehensive Heterocyclic Chemistry I. (ed. by.; Rees, C. W.; Katritzky, A. R.) Pergamon: Oxford, UK, 1984; pp 157–197.
   Google Scholar
  (b) Sato, N. In Comprehensive Heterocyclic Chemistry II. Vol 6. (ed. Scriven, E.F.V., Rees, C.W.; Katritzky, A.R.) Pergamon: Oxford, UK, 1996; pp 233–278.
   Google Scholar
• (a) Wermuth, C. G.; Bourguignon, J. J.; Schlewer, G.; Gies, J. P.; Schoenfelder, A.; Melikian, A.; Bouchet, M. J.; Chantreux, D.; Molimard, J. C.; Heaulme, M.; et al. Synthesis and Structure-Activity Relationships of a Series of Aminopyridazine Derivatives of Gamma-Aminobutyric Acid Acting as Selective GABA-A Antagonists. J. Med. Chem. 1987, 30, 239–249. DOI: 10.1021/jm00385a003.
   PubMed Web of Science ®Google Scholar
  (b) Gleave, R. J.; Beswick, P. J.; Brown, A. J.; Giblin, G. M. P.; Goldsmith, P.; Haslam, C. P.; Mitchell, W. L.; Nicholson, N. H.; Page, L. W.; Patel, S.; et al. Synthesis and Evaluation of 3-Amino-6-Aryl-Pyridazines as Selective CB2 Agonists for the Treatment of Inflammatory Pain. Bioorg. Med. Chem. Lett. 2010, 20, 465–468. DOI: 10.1016/j.bmcl.2009.11.117.
   PubMedGoogle Scholar
  (c) Ballatore, C.; Brunden, K. R.; Piscitelli, F.; James, M. J.; Crowe, A.; Yao, Y.; Hyde, E.; Trojanowski, J. Q.; Lee, V. M. Y.; Smith, A. B. Discovery of Brain-Penetrant, Orally Bioavailable Aminothienopyridazine Inhibitors of Tau Aggregation. J Med Chem. 2010, 53, 3739–3747. DOI: 10.1021/jm100138f.
   PubMed Web of Science ®Google Scholar
  (d) Altenbach, R. J.; Adair, R. M.; Bettencourt, B. M.; Black, L. A.; Fix-Stenzel, S. R.; Gopalakrishnan, S. M.; Hsieh, G. C.; Liu, H.; Marsh, K. C.; McPherson, M. J.; et al. Structure − Activity Studies on a Series of a 2-Aminopyrimidine-Containing Histamine H 4 Receptor Ligands. J. Med. Chem. 2008, 51, 6571–6580. DOI: 10.1021/jm8005959.
   PubMed Web of Science ®Google Scholar
  (e) Gadhachanda, V. R.; Wu, B.; Wang, Z.; Kuhen, K. L.; Caldwell, J.; Zondler, H.; Walter, H.; Havenhand, M.; He, Y. 4-Aminopyrimidines as Novel HIV-1 Inhibitors. Bioorg. Med. Chem. Lett. 2007, 17, 260–265. DOI: 10.1016/j.bmcl.2006.09.047.
   PubMedGoogle Scholar
  (f)Charrier, J.-D.; Durrant, S. J.; Golec, J. M. C.; Kay, D. P.; Knegtel, R. M. A.; MacCormick, S.; Mortimore, M.; O’Donnell, M. E.; Pinder, J. L.; Reaper, P. M.; et al. Discovery of Potent and Selective Inhibitors of Ataxia Telangiectasia Mutated and Rad3 Related (ATR) Protein Kinase as Potential Anticancer Agents. J. Med. Chem. 2011, 54, 2320–2330. DOI: 10.1021/jm101488z.
   PubMed Web of Science ®Google Scholar
• Wrobleski, S. T.; Moslin, R.; Lin, S.; Zhang, Y.; Spergel, S.; Kempson, J.; Tokarski, J. S.; Strnad, J.; Zupa-Fernandez, A.; Cheng, L.; et al. Highly Selective Inhibition of Tyrosine Kinase 2 (TYK2) for the Treatment of Autoimmune Diseases: Discovery of the Allosteric Inhibitor BMS-986165. J. Med. Chem. 2019, 62, 8973–8995. DOI: 10.1021/acs.jmedchem.9b00444.
   PubMed Web of Science ®Google Scholar
• Liang, C.; Ma, Y.; He, W. PCT Int. Appl. 2017, WO2017206924 A1.
   Google Scholar
• (a) Klein, M.; Sandner, P.; Frey, R.; Riedl, B.; Christensen, O. PCT Int. Appl 2007, WO2007118602.
   Google Scholar
  (b) Turck, A.; Ple, N.; Mojovic, L.; Queguiner, G. Diazines. VII. A new synthetic route to the pyridazine antidepressant, minaprine using ortho-directed metalation and Suzuki cross-coupling reactions Bull. Soc. Chim. Fr. 1993, 130, 488–492.
   Google Scholar
• Armer, R.; Bingham, M.; Bhamra, I.; Tuffnell, A. PCT Int. Appl. 2015, WO 2015001348.
   Google Scholar
• Kyle, D. J.; Sun, Q. PCT Int. Appl. 2014, WO2004011441.
   Google Scholar
• Clay, J.-M.; Hipskind, P. A.; Sall, D. J.; Wilson, T.; Thompson, M. L.; Bastian, J. A. PCT Int. Appl. 2010, WO 2010056620.
   Google Scholar
• Schmitt, M.; Araújo-Júnior, J.; Oumouch, S.; Bourguignon, J.-J. Use of 4-Bromo Pyridazine 3,6-Dione for Building 3-Amino Pyridazine Libraries. Mol Divers. 2006, 10, 429–434. DOI: 10.1007/s11030-006-9020-x.
   PubMed Web of Science ®Google Scholar
• Voss, F.; Ritter, S.; Nordhoff, S.; Wachten, S.; Oberboersch, S.; Kless, A. PCT Int. Appl. 2015, WO 2015022073.
   Google Scholar
• Wang, C.; Zhu, M.; Lu, X.; Wang, H.; Zhao, W.; Zhang, X.; Dong, X. Synthesis and Evaluation of Novel Dimethylpyridazine Derivatives as Hedgehog Signaling Pathway Inhibitors. Bioorg. Med. Chem. 2018, 26, 3308–3320. DOI: 10.1016/j.bmc.2018.04.058.
   PubMedGoogle Scholar
• Armer, R.; Bingham, M.; Bhamra, I.; McCarroll, A. PCT Int. Appl. 2014, WO 2014191737.
   Google Scholar
• (a) Ayscough, A. P.; Showell, G. A.; Teall, M. R.; Temple, H. E.; Ahmed, S. PCT Int. Appl. 2010, WO2010092342.
   Google Scholar
  (b) Tafesse, L.; Sun, Q.; Schmid, L.; Valenzano, K. J.; Rotshteyn, Y.; Su, X.; Kyle, D. J. Synthesis and Evaluation of Pyridazinylpiperazines as Vanilloid Receptor 1 Antagonists. Bioorg. Med. Chem. Lett. 2004, 14, 5513–5519. DOI: 10.1016/j.bmcl.2004.09.010.
   PubMed Web of Science ®Google Scholar
• (a) Patrick, D. A.; Bakunov, S. A.; Bakunova, S. M.; Wenzler, T.; Brun, R.; Tidwell, R. R. Antiprotozoal Activity of Dicationic 3,5-Diphenylisoxazoles, Their Prodrugs and Aza-Analogues. Bioorg. Med. Chem. 2014, 22, 559–576. DOI: 10.1016/j.bmc.2013.10.050.
   PubMed Web of Science ®Google Scholar
  (b) Baldwin, J. J.; Mensler, K.; Ponticello, G. S. A Novel Naphthyridinone Synthesis via Enamine Cyclization. J. Org. Chem. 1978, 43, 4878–4880. DOI: 10.1021/jo00419a037.
   Web of Science ®Google Scholar
  (c) Ganser, C.; Lauermann, E.; Maderer, A.; Stauder, T.; Kramb, J.-P.; Plutizki, S.; Kindler, T.; Moehler, M.; Dannhardt, G. Novel 3-Azaindolyl-4-Arylmaleimides Exhibiting Potent Antiangiogenic Efficacy, Protein Kinase Inhibition, and Antiproliferative Activity. J. Med. Chem. 2012, 55, 9531–9540. DOI: 10.1021/jm301217c.
   PubMed Web of Science ®Google Scholar
  (d) Zhu, J.; Wong, H.; Zhang, Z.; Yin, Z.; Meanwell, N. A.; Kadow, J. F.; Wang, T. An Effective Procedure for the Preparation of 3-Substituted-4- or 6-Azaindoles from Ortho-Methyl Nitro Pyridines. Tetrahedron Lett. 2006, 47, 5653–5656. DOI: 10.1016/j.tetlet.2006.06.017.
   Web of Science ®Google Scholar
• Meerwein, H.; Florian, W.; Schon, N.; Stopp, G. Über Säureamidacetale, Harnstoffacetale Und Lactamacetale. Justus Liebigs Ann. Chem. 1961, 641, 1–39. DOI: 10.1002/jlac.19616410102.
   Google Scholar
• Reich, M. F.; Fabio, P. F.; Lee, V. J.; Kuck, N. A.; Testa, R. T. Pyrido[3,4-e]-1,2,4-Triazines and Related Heterocycles as Potential Antifungal Agents. J. Med. Chem. 1989, 32, 2474–2485. DOI: 10.1021/jm00131a010.
   PubMed Web of Science ®Google Scholar
• (a) Copar, A.; Stanovnik, B.; Tisler, M. Amino Acids in the Synthesis of Heterocyclic Systems a Novel Synthesis of Fused Pyridinones. Bull. Soc. Chim. Belges. 2010, 100, 533–538. DOI: 10.1002/bscb.19911000708.
   Google Scholar
  (b) Vors, J. P. A Novel Approach to the Pyrido[4,3-c]Pyridazine Ring. Synthesis of Pyrido[4,3-c]Pyridazin-5(6 H)-One from 3,4-Disubstituted Pyridazines. J. Het. Chem. 1991, 28, 1043–1046. DOI: 10.1002/jhet.5570280435.
   Web of Science ®Google Scholar
  (c) Bachmann, M.; Neunhoeffer, H. Cycloadditionen Mit Azabenzolen, XIII. Reaktionen Von 1,2,4,5-Tetrazinen Mit Fulvenen. Liebigs Ann. Chem. 1979, 1979, 675–688. DOI: 10.1002/jlac.197919790511.
   Google Scholar
• (a) Abu-Shanab, F. A.; Elkholy, Y. M.; Elnagdi, M. H. Enaminones as Building Blocks in Organic Synthesis: Synthesis of New Polyfunctional Pyridines, Condensed Pyridines, and Penta Substituted Benzene. Synth. Commun. 2002, 32, 3493–3502. DOI: 10.1081/SCC-120014783.
   Web of Science ®Google Scholar
  (b) Vilar, J.; Quintela, J. M.; Peinador, C.; Veiga, C.; Ojea, V. Synthesis of 1,7,10-Anthyridine Derivatives. Heterocycles 1993, 36, 2697–2705. DOI: 10.3987/COM-93-6464.
   Web of Science ®Google Scholar
  (c) Balogh, M.; Hermecz, I.; Simon, K.; Pusztay, L. Studies on Naphthyridines. Part 2. Synthesis of 4-Substituted and 6-Substituted 1,6-Naphthyridin-5(6H)-Ones. J. Het. Chem 2009, 26, 1755–1769. DOI: 10.1002/jhet.5570260644.
   Google Scholar
  (d) Chupp, J. P.; Molyneaux, J. M. Derivation of Fluorine-Containing Pyridine Dicarboxylates. II. Elaboration at the 4-Position. J. Het. Chem 1989, 26, 645–653. DOI: 10.1002/jhet.5570260325.
   Web of Science ®Google Scholar
• (a) Fischer, G. W. Tetrazole Compounds. 9. A New Approach to Tetrazolyl-Substituted Quinoline Derivatives. J. Het. Chem 1994, 31, 1529–1534. DOI: 10.1002/jhet.5570310642.
   Web of Science ®Google Scholar
  (b) Fischer, G. W. Tetrazolverbindungen. 5. Synthese Und Umaminierung Von Enaminoketonen Der Tetrazolreihe. J. Prakt. Chem. 1990, 332, 977–994. DOI: 10.1002/prac.19903320615.
   Google Scholar
  (c) Fischer, G. W. Tetrazolverbindungen. 3. Modifizierung Von (1-Aryl-1H-Tetrazol-5-yl)-acetaldehyd-Enaminen Durch Säurekatalysierte Umaminierung. J. Prakt. Chem. 1988, 330, 981–992. DOI: 10.1002/prac.19883300619.
   Google Scholar
• (a) Fu, Y.; Lu, Z.; Fang, K.; He, X.; Xu, H.; Hu, Y. Enzymatic Approach to Cascade Synthesis of Bis(Indolyl)Methanes in Pure Water. RSC Adv. 2020, 10, 10848–10853. DOI: 10.1039/C9RA10014H.
   PubMed Web of Science ®Google Scholar
  (b) Mathavan, S.; Kannan, K.; Yamajala, R. B. R. D. Thiamine Hydrochloride as a Recyclable Organocatalyst for the Synthesis of Bis(Indolyl)Methanes, Tris(Indolyl)Methanes, 3,3-di(Indol-3-yl)Indolin-2-Ones and Biscoumarins. Org. Biomol. Chem. 2019, 17, 9620–9626. and references cited therein. DOI: 10.1039/C9OB02090J.
   PubMed Web of Science ®Google Scholar
• (a) Guo, S.; Fang, Z.; Zhou, B.; Hua, J.; Dai, Z.; Yang, Z.; Liu, C.; He, W.; Guo, K. Cu/Pd-Catalyzed Chemoselective Synthesis of C-3 Dicarbonyl Indoles and Bis(Indolyl)Alkanes from Aldehydes and Indoles. Org. Chem. Front. 2019, 6, 627–631. DOI: 10.1039/C8QO01206G.
   Google Scholar
  (b) Ishii, H.; Murakami, K.; Sakurada, E.; Hosoya, K.; Murakami, Y. Polymerisation of Indole. Part 2. A New Indole Trimer. J. Chem. Soc., Perkin Trans. 1 1988, 8, 2377–2385. DOI: 10.1039/P19880002377.
   Google Scholar
  (c) Jella, R. R.; Nagarajan, R. Synthesis of Indole Alkaloids Arsindoline A, Arsindoline B and Their Analogues in Low Melting Mixture. Tetrahedron. 2013, 69, 10249–10253. DOI: 10.1016/j.tet.2013.10.037.
   Web of Science ®Google Scholar
• Chakrabarty, M.; Ghosh, N.; Basak, R.; Harigaya, Y. A Facile and Efficient Synthesis of 2,2‐Bis(3′/2′‐Indolyl)Ethylamines and Three Bisindolic Natural Products. Synth. Commun. 2004, 34, 421–434. DOI: 10.1081/SCC-120027281.
   Web of Science ®Google Scholar
• Xia, D.; Wang, Y.; Du, Z.; Zheng, Q.-Y.; Wang, C. Rhenium-Catalyzed Regiodivergent Addition of Indoles to Terminal Alkynes. Org. Lett. 2012, 14, 588–591. DOI: 10.1021/ol203199m.
   PubMed Web of Science ®Google Scholar