Three-component reaction between 2-hydroxymethyl-5-phenylamino-pyran-4-one and aromatic acyl chlorides with potassium selenocyanate: Synthesis of 2-aryl-6-hydroxymethyl-1-phenyl-4-selenoxo-1,4-dihydro-pyrano[3,2-d]pyrimidin-8-one

References

• Gangjee, A.; Adair, O.; Queener, S. Synthesis and Biological Evaluation of 2,4-Diamino-6-(Arylaminomethyl)Pyrido[2,3-d]Pyrimidines as Inhibitors of Pneumocystis carinii and Toxoplasma gondii Dihydrofolate Reductase and as Antiopportunistic Infection and Antitumor Agents. J. Med. Chem. 2003, 46, 5074–5082. DOI: 10.1021/jm030312n.
   PubMed Web of Science ®Google Scholar
• Ghorab, M. M.; Ragab, F. A.; Heiba, H. I.; Arafa, R. K.; El-Hossary, E. M. In Vitro Anticancer Screening and Radiosensitizing Evaluation of Some New Quinolines and Pyrimido[4,5-b]Quinolines Bearing a Sulfonamide Moiety. Eur. J. Med. Chem. 2010, 45, 3677–3684. DOI: 10.1016/j.ejmech.2010.05.014.
   PubMed Web of Science ®Google Scholar
• El-Gazzar, A. R.; Hafez, H. Synthesis of 4-Substituted Pyrido[2,3-d]Pyrimidin-4(1H)-One as Analgesic and anti-Inflammatory Agents. Bioorg. Med. Chem. Lett. 2009, 19, 3392–3397. DOI: 10.1016/j.bmcl.2009.05.044.
   PubMed Web of Science ®Google Scholar
• El-Sayed, O.; Aboul-Enein, H. Synthesis and Antimicrobial Activity of Novel Pyrazolo[3,4-b]Quinoline Derivatives. Arch. Pharm. Pharm. Med. Chem. 2001, 334, 117–120. DOI: 10.1002/1521-4184(200104)334:4 < 117::AID-ARDP117 > 3.0.CO;2-9.
   PubMed Web of Science ®Google Scholar
• Quintela, J. M.; Peinador, C.; Botana, L.; Estévez, M.; Riguera, R. Synthesis and Antihistaminic Activity of 2-Guanadino-3-Cyanopyridines and Pyrido[2,3-d]-Pyrimidines. Bioorg. Med. Chem. 1997, 5, 1543–1553. DOI: 10.1016/S0968-0896(97)00108-9.
   PubMed Web of Science ®Google Scholar
• Katritzky, A. R. Conformational Equilibria in Nitrogen-Containing Saturated Six-Membered Rings. Adv. Heterocycl. Chem. 1984, 36, 1–173. DOI: 10.1098/rsbm.2015.0001.
   Web of Science ®Google Scholar
• Choudhury, A.; Chen, H.; Nilsen, C. N.; Sorgi, K. L. A Chemoselective Aniline–Chloropyrimidine Coupling in a Competing Electrophilic Environment. Tetrahedron Lett. 2008, 49, 102–105. DOI: 10.1016/j.tetlet.2007.11.009.
   Web of Science ®Google Scholar
• Kappe, C. O. 4-Aryldihydropyrimidines via the Biginelli Condensation: Aza-Analogs of Nifedipine-Type Calcium Channel Modulators. Molecules. 1998, 3, 1–9. DOI: 10.3390/30100001.
   Web of Science ®Google Scholar
• Dabiri, M.; Arvin-Nezhad, H.; Khavasi, H. R.; Bazgir, A. A Novel and Efficient Synthesis of pyrimido4,5-Dpyrimidine-2,4,7-Trione and pyrido2,3-d: 6,5-d Dipyrimidine-2,4,6,8-Tetrone Derivatives. Tetrahedron. 2007, 63, 1770–1774. DOI: 10.1016/j.tet.2006.12.043.
   Web of Science ®Google Scholar
• Samai, S.; Chandra Nandi, G.; Chowdhury, S.; Shankar Singh, M. l-Proline Catalyzed Synthesis of Densely Functionalized Pyrido[2,3-d]Pyrimidines via Three-Component One-Pot Domino Knoevenagel aza-Diels–Alder Reaction. Tetrahedron. 2011, 67, 5935–5941. DOI: 10.1016/j.tet.2011.06.051.
   Web of Science ®Google Scholar
• Molina, P.; Vilaplana, M. J.; Pérez, J. Iminophosphorane-Mediated Synthesis of Fused Uracils. A Faclle One-Pot Preparation of Pyrimido[4,5-d]Pyrimidine Derivatives. Tetrahedron. 1990, 46, 7855–7864. DOI: 10.1016/S0040-4020(01)90083-3.
   Web of Science ®Google Scholar
• Abdel-Hafez, S. H.; Ahmed, R. A.; Abdel-Azim, M. A.; Hassan, K. M. Selenium Containing Heterocycles: Part 1. Synthesis of Some New Substituted Pyrido[3′,2′:4,5]Selenolo[3,2-d]Pyrimidines and Related Fused Tetracyclic Systems. J. Chem. Res. 2007, 2007, 580–584. DOI: 10.3184/030823407X25506.
   Google Scholar
• Abdel-Hafez, S. H. Selenium-Containing Heterocycles. Synthesis and Reactions of 2-Amino-4,5,6,7-Tetrahydro-1-Benzoselenophene-3-Carbonitrile with Anticipated Biological Activity. Russ. J. Org. Chem. 2005, 41, 396–401. DOI: 10.1007/s11178-005-0177-z.
   Web of Science ®Google Scholar
• Douglass, 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
• Duddeck, H. 77Se NMR Spectroscopy and Its Applications in Chemistry. Annu. Rep. NMR Spectrosc. 2004, 52, 105–166. DOI: 10.1016/S0066-4103(04)52003-3.
   Web of Science ®Google Scholar