Base promoted synthesis of 3-benzyl-2,5-diarylpyrazines from arylaldehydes and α-amino ketones

References

• (a) Cavalier, J.-F.; Burton, M.; Dussart, F.; Marchand, C.; Rees, J.-F.; Marchand-Brynaert, J. Catechol Derivatives of Aminopyrazine and Cell Protection against Uvb-Induced Mortality. J. Bioorg. Med. Chem. 2001, 9, 1037–1044. DOI: 10.1016/S0968-0896(00)00321-7.
   PubMed Web of Science ®Google Scholar
  (b) Wu, X. A.; Zhao, Y. M.; Yu, N. J. A Novel Analgesic Pyrazine Derivative from the Leaves of Croton tiglium L. J. Asian Nat. Prod. Res. 2007, 9, 437–441. DOI: 10.1080/10286020500384781.
   PubMed Web of Science ®Google Scholar
  (c) Asaki, T.; Kuwano, K.; Morrison, K.; Gatfield, J.; Hamamoto, T.; Clozel, M. Selexipag: An Oral and Selective IP Prostacyclin Receptor Agonist for the Treatment of Pulmonary Arterial Hypertension. J. Med. Chem. 2015, 58, 7128–7137. DOI: 10.1021/acs.jmedchem.5b00698.
   PubMed Web of Science ®Google Scholar
  (d) Gohlke, H.; Gündisch, D.; Schwarz, S.; Seitz, G.; Tilotta, M. C.; Wegge, T. Synthesis and Nicotinic Binding Studies on Enantiopure Diazine Analogues of the Novel (2-Chloro-5-Pyridyl)-9-Azabicyclo[4.2.1]Non-2-Ene UB-165. J. Med. Chem. 2002, 45, 1064–1072. DOI: 10.1021/jm010936y.
   PubMed Web of Science ®Google Scholar
  (e) Berkers, C. R.; Leestemaker, Y.; Schuurman, K. G.; Ruggeri, B.; Jones-Bolin, S.; Williams, M.; Ovaa, H. Probing the Specificity and Activity Profiles of the Proteasome Inhibitors Bortezomib and Delanzomib. Mol. Pharmaceutics. 2012, 9, 1126–1135. DOI: 10.1021/mp2004143.
   PubMed Web of Science ®Google Scholar
  (f) Hirsh, A. J.; Molino, B. F.; Zhang, J.; Astakhova, N.; Geiss, W. B.; Sargent, B. J.; Swenson, B. D.; Usyatinsky, A.; Wyle, M. J.; Boucher, R. C.; et al. Design, Synthesis, and Structure−Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers: Drugs for Cystic Fibrosis and Chronic Bronchitis. J. Med. Chem. 2006, 49, 4098–4115. DOI: 10.1021/jm051134w.
   PubMed Web of Science ®Google Scholar
  (g) Rahmani, R.; Ban, K.; Jones, A. J.; Ferrins, L.; Ganame, D.; Sykes, M. L.; Avery, V. M.; White, K. L.; Ryan, E.; Kaiser, M.; et al. 6-Arylpyrazine-2-Carboxamides: A New Core for Trypanosoma Brucei Inhibitors. J. Med. Chem. 2015, 58, 6753–6765. DOI: 10.1021/acs.jmedchem.5b00438.
   PubMed Web of Science ®Google Scholar
  (h) Younis, Y.; Douelle, F.; Gonzalez Cabrera, D.; Le Manach, C.; Nchinda, A. T.; Paquet, T.; Street, L. J.; White, K. L.; Zabiulla, K. M.; Joseph, J. T.; et al. Structure–Activity-Relationship Studies around the 2-Amino Group and Pyridine Core of Antimalarial 3,5-Diarylaminopyridines Lead to a Novel Series of Pyrazine Analogues with Oral in Vivo Activity. J. Med. Chem. 2013, 56, 8860–8871. DOI: 10.1021/jm401760c.
   PubMed Web of Science ®Google Scholar
  (i) Berg, S.; Bergh, M.; Hellberg, S.; Hogdin, K.; Lo-Alfredsson, Y.; Soderman, P.; von Berg, S.; Weigelt, T.; Ormo, M.; Xue, Y.; et al. Discovery of Novel Potent and Highly Selective Glycogen Synthase Kinase-3β (GSK3β) Inhibitors for Alzheimer’s Disease: Design, Synthesis, and Characterization of Pyrazines. J. Med. Chem. 2012, 55, 9107–9119. DOI: 10.1021/jm201724m.
   PubMed Web of Science ®Google Scholar
  (j)Fruit, C.; Turck, A.; Plé, N.; Mojovic, L.; Quéguiner, G. A New Route to Septorin via Controlled Metalations of Pyrazines. Diazines XXX. G. Tetrahedron. 2001, 57, 9429–9435. DOI: 10.1016/S0040-4020(01)00950-4.
   Web of Science ®Google Scholar
  (k) Lainchbury, M.; Matthews, T. P.; McHardy, T.; Boxall, K. J.; Walton, M. I.; Eve, P. D.; Hayes, A.; Valenti, M. R.; de Haven Brandon, A. K.; Box, G.; et al. J. Med. Chem. 2012, 55, 10229. DOI: 10.1021/jm3012933.
   PubMed Web of Science ®Google Scholar
  (l) Durán, R.; Zubía, E.; Ortega, M. J.; Naranjo, S.; Salvá, J. Tetrahedron. 1999, 55, 13225. DOI: 10.1016/S0040-4020(99)00803-0.
   Web of Science ®Google Scholar
• (a) Brophy, J.; Cavill, G. Naturally Occurring Pyrazines and Their Mass Spectrometric Characterisation. G. Heterocycles 1980, 14, 477. DOI: 10.3987/R-1980-04-0477.
   Web of Science ®Google Scholar
  (b)Seeman, J. I.; Ennis, D. M.; Sector, H. V.; Clawson, L.; Palen, J. The Perceptual Similarity of Substitued Benzenes and Pyridines as a Funciton of Steric Hindrance. Chem. Senses. 1989, 14, 395–405. DOI: 10.1093/chemse/14.3.395.
   Web of Science ®Google Scholar
  (c) Fales, H. M.; Blum, M. S.; Southwick, E. W.; Williams, D. L.; Roller, P. P.; Don, A. W. Structure and Synthesis of Tetrasubstituted Pyrazines in Ants in the Genus. Tetrahedron. 1988, 44, 5045–5050. DOI: 10.1016/S0040-4020(01)86009-9.
   Web of Science ®Google Scholar
  (d) Tecle, B.; Sun, C. M.; Brophy, J. J.; Toia, R. F. Novel Pyrazines from the Head of Australian Ponerine antRhytidoponera Metallica. J. Chem. Ecol. 1987, 13, 1811–1822. DOI: 10.1007/BF01013230.
   PubMed Web of Science ®Google Scholar
  (e) Wheeler, J. W.; Avery, J.; Olubajo, O.; Shamin, M. T.; Storm, C. B.; Duffield, R. M. Alkylpyrazines from Hymenoptera. Tetrahedron. 1982, 38, 1939–1948. DOI: 10.1016/0040-4020(82)80043-4.
   Web of Science ®Google Scholar
• Rajagopalan, R.; Neumann, W. L.; Poreddy, A. R.; Fitch, R. M.; Freskos, J. N.; Asmelash, B.; Gaston, K. R.; Galen, K. P.; Shieh, J. J.; Dorshow, R. B. Hydrophilic Pyrazine Dyes as Exogenous Fluorescent Tracer Agents for Real-Time Point-of-Care Measurement of Glomerular Filtration Rate. J. Med. Chem. 2011, 54, 5048–5058. DOI: 10.1021/jm200257k.
   PubMed Web of Science ®Google Scholar
• Buechi, G.; Galindo, J. J. Regioselective Synthesis of Alkylpyrazines. J. Org. Chem. 1991, 56, 2605–2606. DOI: 10.1021/jo00008a002.
   Web of Science ®Google Scholar
• Aparicio, D.; Attanasi, O. A.; Filippone, P.; Ignacio, R.; Lillini, S.; Mantellini, F.; Palacios, F.; de Los Santos, J. M. Straightforward Access to Pyrazines, Piperazinones, and Quinoxalines by Reactions of 1,2-Diaza-1,3-Butadienes with 1,2-Diamines under Solution, Solvent-Free, or Solid-Phase Conditions. J. Org. Chem. 2006, 71, 5897–5905. DOI: 10.1021/jo060450v.
   PubMed Web of Science ®Google Scholar
• Elmaaty, T. A.; Castle, L. W. Facile Regiocontrolled Synthesis of Trialkyl-Substituted Pyrazines. Org. Lett. 2005, 7, 5529–5530. DOI: 10.1021/ol0523751.
   PubMed Web of Science ®Google Scholar
• Matsushita, H.; Lee, S. H.; Yoshida, K.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. N − H Insertion Reactions of Boc-Amino Acid Amides: Solution- and Solid-Phase Synthesis of Pyrazinones and Pyrazines. Org. Lett. 2004, 6, 4627–4629. DOI: 10.1021/ol047933a.
   PubMed Web of Science ®Google Scholar
• Taber, D. F.; DeMatteo, P. W.; Taluskie, K. V. Synthesis of Symmetrical and Unsymmetrical Pyrazines. J. Org. Chem. 2007, 72, 1492–1494. DOI: 10.1021/jo061935m.
   PubMed Web of Science ®Google Scholar
• Gnanaprakasam, B.; Balaraman, E.; Ben-David, Y.; Milstein, D. Synthesis of Peptides and Pyrazines from β-Amino Alcohols through Extrusion of H2 Catalyzed by Ruthenium Pincer Complexes: Ligand-Controlled Selectivity. Angew. Chem. Int. Ed. Engl. 2011, 50, 12240–12244. DOI: 10.1002/anie.201105876.
   PubMed Web of Science ®Google Scholar
• Palacios, F.; Ochoa de Retana, A. M.; Gil, J. I.; López de Munain, R. Synthesis of Pyrazine-Phosphonates and -Phosphine Oxides from 2H-Azirines or Oximes. Org. Lett. 2002, 4, 2405–2408. DOI: 10.1021/ol0261534.
   PubMed Web of Science ®Google Scholar
• Ryu, T.; Baek, Y.; Lee, P. H. Synthesis of Pyrazines from Rhodium-Catalyzed Reaction of 2H-Azirines with N-Sulfonyl 1,2,3-Triazoles. J. Org. Chem. 2015, 80, 2376–2383. DOI: 10.1021/acs.joc.5b00036.
   PubMed Web of Science ®Google Scholar
• Loy, N. S.; Kim, S.; Park, C. M. Synthesis of Unsymmetrical Pyrazines Based on α-Diazo Oxime Ethers. Org. Lett. 2015, 17, 395–397. DOI: 10.1021/ol5034173.
   PubMed Web of Science ®Google Scholar
• (a) Thompson, W. J.; Jones, J. H.; Lyle, P. A.; Thies, J. E. J. Org. Chem. 1988, 53, 2052. DOI: 10.1021/jo00244a037.
   Web of Science ®Google Scholar
  (b) Guram, A. S.; Jordan, R. F. Zirconium-Mediated Reactions of Alkylpyrazines and Alkynes. Synthesis of Highly Substituted Alkylpyrazines. J. Org. Chem. 1992, 57, 5994–5999. DOI: 10.1021/jo00048a038.
   Web of Science ®Google Scholar
  (c) Sato, N.; Matsuura, T. Studies on Pyrazines. Part 32. Synthesis of Trisubstituted and Tetrasubstituted Pyrazines as Ant Pheromones. J. Chem. Soc, Perkin Trans. 1. 1996, 19, 2345. DOI: 10.1039/p19960002345.
   Google Scholar
  (d) Mehta, V. P.; Modha, S. G.; Van der Eycken, E. V. Microwave-Assisted Palladium-Catalyzed Phosphonium Coupling of 2(1 H)-Pyrazinones. J. Org. Chem. 2010, 75, 976–979. DOI: 10.1021/jo9024754.
   PubMed Web of Science ®Google Scholar
  (e) Modha, S. G.; Trivedi, J. C.; Mehta, V. P.; Ermolat’ev, D. S.; Van der Eycken, E. V. An Expeditious Route toward Pyrazine-Containing Nucleoside Analogues. J. Org. Chem. 2011, 76, 846–856. DOI: 10.1021/jo102089h.
   PubMed Web of Science ®Google Scholar
  (f) Mehta, V. P.; Sharma, A.; Hecke, K. V.; Meervelt, L. V.; Eycken, E. V. J. Org. Chem. 2008, 73, 2382. DOI: 10.1021/jo702656v.
   PubMed Web of Science ®Google Scholar
  (g) Mosrin, M.; Bresser, T.; Knochel, P. Regio- and Chemoselective Multiple Functionalization of Chloropyrazine Derivatives. Application to the Synthesis of Coelenterazine. Org. Lett. 2009, 11, 3406–3409. DOI: 10.1021/ol901275n.
   PubMed Web of Science ®Google Scholar
  (h) Liu, W.; Wise, D. S.; Townsend, L. B. Dimetalation of Pyrazines. A One-Pot Synthesis of Multisubstituted Pyrazine C -Nucleosides. J. Org. Chem. 2001, 66, 4783–4786. DOI: 10.1021/jo001555f.
   PubMed Web of Science ®Google Scholar
  (i) Buron, F.; Plé, N.; Turck, A.; Queguiner, G. Synthesis of Pyrazine Alcaloids from Botryllus leachi. Diazines 43. J. Org. Chem. 2005, 70, 2616–2621. DOI: 10.1021/jo0478196.
   PubMed Web of Science ®Google Scholar
• Flament, I.; Sonnay, P.; Ohloff, G. Pyrazines III Condensation Des Dihydropyrazines Avec Les Composés Carbonyles: Synthèse De Pyrazines Substituées Et De Dihydro-6, 7-5E-Cyclopenta [b] Pyrazines. Bull. Soc. Chim. Belge. 2010, 88, 941–950. DOI: 10.1002/bscb.19790881115.
   Google Scholar