Synthesis of 4-aryl-7-methoxy-9-thia-[1,3,4a]triazafluorene-2-selones via a three-component condensation of 6-methoxybenzothiazol-2-ylamine, potassium selenocyanate and an acyl chloride

References

• Swinbourne, J. F.; Hunt, H. J.; Klinkert, G. Advances in Indolizine Chemistry. Adv. Heterocycl. Chem. 1987, 23, 103–170. DOI: 10.1016/S0065-2725(08)60842-9.
   Google Scholar
• Hermecz, I.; Vasvari-Debreczy, L.; Matyus, P. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R; Rees, C. W; Scriven, E. V. F. Eds.; Pergamon: London, 1996; Chapter 8.23, pp 563–595.
   Google Scholar
• Vu, C.; Pan, D.; Peng, B.; Kumaravel, G.; Smits, G.; Jin, X.; Phadke, D.; Engber, T.; Huang, C.; Reilly, J.; Tam; et al. Novel Diamino Derivatives of [1,2,4]Triazolo[1,5-a][1,3,5]Triazine as Potent and Selective Adenosine A2a Receptor Antagonists. J. Med. Chem. 2005, 48, 2009–2018. DOI: 10.1021/jm0498396.
   PubMed Web of Science ®Google Scholar
• Ishii, A.; Katsumata, Y. Drugs Poisons Hum: Diazine and Triazine Herbicides; Springer: Berlin, Heidelberg, 2005, Chapter II, pp. 591–597.
   Google Scholar
• Wurthner, F.; Thalacker, C.; Sautter, A.; Schartl, W.; Ibach, W.; Hollricher, O. Hierarchical Self-Organization of Perylene Bisimide-Melamine Assemblies to Fluorescent Mesoscopic Superstructures. Chem. Eur. J. 2000, 6, 3871–3886. DOI: 10.1002/1521-3765.
   PubMed Web of Science ®Google Scholar
• Fang, T.; Shimp, D. A. Polycyanate Esters: Science and Applications. Prog. Poly. Sci. 1995, 20, 61–118. DOI: 10.1016/0079-6700(94)E0006-M.
   Web of Science ®Google Scholar
• Fang, Q.; Jiang, L. Synthesis and Characterization of Triallylphenoxytriazine and the Properties of Its Copolymer with Bismaleimide. J. Appl. Polym. Sci. 2001, 81, 1248–1257. DOI: 10.1002/app.1547.
   Web of Science ®Google Scholar
• Oudir, S.; Rigo, B.; Hénichart, J.-P.; Gautret, P. A Convenient Method for the Conversion of a Carboxy Group into a 4,6-Dimethoxy-1,3,5-Triazine Group: Application to N-Benzylpyroglutamic Acids. Synthesis 2006, 17, 2845–2848. DOI: 10.1055/s-2006-942519.
   Google Scholar
• Mikhaylichenko, S. N.; Patel, S. M.; Dalili, S.; Chesnyuk, A. A.; Zaplishny, V. N. Synthesis and Structure of New 1,3,5-Triazine-Pyrazole Derivatives. Tetrahedron Lett. 2009, 50, 2505–2508. DOI: 10.1016/j.tetlet.2009.03.054.
   Web of Science ®Google Scholar
• Díaz-Ortiz, A.; de la Hoz, A.; Moreno, A.; Sánchez-Migallón, A.; Valiente, G. Synthesis of 1,3,5-Triazines in Solvent-Free Conditions Catalysed by Silica Supported Lewis Acid. Green Chem. 2002, 4, 339–343. DOI: 10.1039/B202014A.
   Web of Science ®Google Scholar
• Afonso, C. A. M.; Lourenco, N. M. T.; Rosatella, A. A. Synthesis of 2, 4, 6-Tri-Substituted-1, 3, 5-Triazines. Molecules 2006, 11, 81–102. DOI: 10.3390/11010081.
   PubMed Web of Science ®Google Scholar
• Brown, H. C.; Cheng, M. T. Synthesis of Perfluoroallyl-Substituted 1,3,5-Triazines. J. Chem. Eng. Data 1968, 13, 560–561.
   Web of Science ®Google Scholar
• Peng, J.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Use of a Selone Chiral Derivatizing Agent for the Absolute Configurational Assignment of Stereogenic Center. Tetrahedron: Asymmetry 1994, 5, 1627–1630. DOI: 10.1016/0957-4166(94)80066-9.
   Google Scholar
• Silks, L. A.; Kimball, D. B.; Hatch, D.; Ollivault-Shiflett, M.; Michalczyk, R.; Moody, E. Chiral N-Acetyl Selone-Promoted Aldol Reactions. Synth. Commun. 2009, 39, 641–653. DOI: 10.1080/00397910802419706.
   Web of Science ®Google Scholar
• Okazaki, R.; Tokitoh, N. Heavy Ketones, the Heavier Element Congeners of a Ketone. Acc. Chem. Res. 2000, 33, 625–630. DOI: 10.1021/ar980073b.
   PubMed Web of Science ®Google Scholar
• Erker, G.; Hock, R.; Krüger, C.; Werner, S.; Klärner, F. G.; Artschwager-Perl, U. Synthesis and Cycloadditions of Monomeric Selenobenzophenone. Angew. Chem. Int. Ed. Engl. 1990, 29, 1067–1068. DOI: 10.1002/anie.199010671.
   Web of Science ®Google Scholar
• Wirth, T. Organoselenium Chemistry: Synthesis and Reactions; Wiley-VCH, Weinheim, Germany, 2012; p. 1–51
   Google Scholar
• Sydnes, M. O.; Isobe, M. Exclusive Formation of Azo-Compounds upon Hydrogenolysis of Nitrobenzeneseleninic Acid Derivatives over Pd/C. Monatsh. Chem. 2015, 146, 351–356. DOI: 10.1007/s00706-014-1373-8.
   Web of Science ®Google Scholar
• Razus, A. C.; Birzan, L.; Hanganu, A.; Cristea, M.; Ungureanu, E.-M.; Soare, M.-L.; Buica, G.-O. 1-Phenylselanylazulenes: Synthesis and Selenium Atom Oxidation. Monatsh. Chem. 2014, 145, 1999–2009. DOI: 10.1007/s00706-014-1297-3.
   Web of Science ®Google Scholar
• Rvovic, M. D.; Divac, V. M.; Jankovic, N. Z.; Bugarcic, Z. M. Cyclization of Some Terpenic Alcohols by Phenylselenoetherification Reaction. Monatsh. Chem. 2013, 144, 1227–1231. DOI: 10.1007/s00706-013-1006-7.
   Web of Science ®Google Scholar
• Filipovic, N.; Polovic, N.; Raskovic, B.; Misirlic-Dencic, S.; Dulovic, M.; Savic, M.; Niksic, M.; Mitic, D.; Andelkovic, K.; Todorovic, T. Biological Activity of Two Isomeric N-Heteroaromatic Selenosemicarbazones and Their Metal Complexes. Monatsh. Chem. 2014, 145, 1089–1099. DOI: 10.1007/s00706-014.
   Web of Science ®Google Scholar
• Douglas, I. B. Acylselenoureas. J. Am. Chem. Soc. 1937, 59, 740–742. DOI: 10.1021/ja01283a041.
   Google Scholar
• Yavari, I.; Mosaferi, S. A One-Pot Synthesis of 2H-Pyrido[1,2-a][1,3,5]Triazine-2-Selenones from Acyl Isoselenocyanates and Pyridin-2-Amine. Monatsh. Chem. 2017, 148, 963–966. DOI: 10.1007/s00706-016-1834-3.
   Web of Science ®Google Scholar
• Zhiani, R. Synthesis of 4-Selenylidene-4H,5H-Chromeno[3,4-e][1,3]Oxazin-5-One. J. Chem. Res. 2017, 41, 452–454. DOI: 10.3184/174751917X15000317104501.
   Web of Science ®Google Scholar
• Zhiani, R. Synthesis of 1,2,4-Triazole-3-Selenones via Three-Component Reaction between Benzohydrazide, Potassium Selenocyanate and Acyl Chlorides under Solvent-Free Conditions. J. Chem. Res. 2017, 41, 455–456. DOI: 10.3184/174751917X15000317104510.
   Web of Science ®Google Scholar
• Boccanfuso, A. M.; Griffin, D. W.; Dunlap, R. B.; Odom, J. D. The Reaction of p-Tolyl Lsoselenocyanate with Primary and Secondary Amines: A Multinuclear Magnetic Resonance Study. Bioorg. Chem 1989, 17, 231–239. DOI: 10.1016/0045-2068(89)90023-0.
   Web of Science ®Google Scholar