Facile and efficient synthesis of quinazoline-2,4(1H,3H)-diones through sequential hydrogenation condensation

References

• Khan, I.; Ibrar, A.; Ahmed, W.; Saeed, A. Synthetic Approaches, Functionalization and Therapeutic Potential of Quinazoline and Quinazolinone Skeletons: The Advances Continue. Eur. J. Med. Chem. 2015, 90, 124–169. DOI: 10.1016/j.ejmech.2014.10.084.
   PubMed Web of Science ®Google Scholar
• Carrico, D.; Blaskovich, M. A.; Bucher, C. J.; Sebti, S. M.; Hamilton, A. D. Design, Synthesis, and Evaluation of Potent and Selective Benzoyleneurea-Based Inhibitors of Protein Geranylgeranyltransferase-I. Bioorg. Med. Chem. 2005, 13, 677–688. DOI: 10.1016/j.bmc.2004.10.053.
   PubMedGoogle Scholar
• Colotta, V.; Lenzi, O.; Catarzi, D.; Varano, F.; Squarcialupi, L.; Costagli, C.; Galli, A.; Ghelardini, C.; Pugliese, A. M.; Maraula, G; 3-Hydroxy-1H-Quinazoline-2,4-Dione Derivatives as New Antagonists at Ionotropic Glutamate Receptors: Molecular Modeling and Pharmacological Studies. Eur. J. Med. Chem. 2012, 54, 470–482. DOI: 10.1016/j.ejmech.2012.05.036.
   PubMed Web of Science ®Google Scholar
• Mortier, J.; Masereel, B.; Remouchamps, C.; Ganeff, C.; Piette, J.; Frederick, R. NF-κB Inducing Kinase (NIK) Inhibitors: Identification of New Scaffolds Using Virtual Screening. Bioorg. Med. Chem. Lett. 2010, 20, 4515–4520. DOI: 10.1016/j.bmcl.2010.06.027.
   PubMed Web of Science ®Google Scholar
• Piotrowska, D. G.; Andrei, G.; Schols, D.; Snoeck, R.; Łysakowska, M. Synthesis, Anti-Varicella-Zoster Virus and Anti-Cytomegalovirus Activity of Quinazoline-2,4-Diones Containing Isoxazolidine and Phosphonate Substructures. Eur. J. Med. Chem. 2017, 126, 84–100. DOI: 10.1016/j.ejmech.2016.10.002.
   PubMed Web of Science ®Google Scholar
• Abdel-Magid, A. F. Potential Treatment for Neuropsychiatry Disorders with TRPC5 Modulators. ACS Med. Chem. Lett. 2016, 7, 547–548. DOI: 10.1021/acsmedchemlett.6b00182.
   PubMed Web of Science ®Google Scholar
• Ismail, M. A. H.; Barker, S.; Abou El Ella, D. A.; Abouzid, K. A. M.; Toubar, R. A.; Todd, M. H. Design and Synthesis of New Tetrazolyl- and Carboxy-Biphenylylmethyl-Quinazolin-4-One Derivatives as Angiotensin II AT1 Receptor Antagonists. J. Med. Chem. 2006, 49, 1526–1535. DOI: 10.1021/jm050232e.
   PubMed Web of Science ®Google Scholar
• Yoo, E.; Salunke, D. B.; Sil, D.; Guo, X.-Q.; Salyer, A. C. D.; Hermanson, A. R.; Kumar, M.; Malladi, S. S.; Balakrishna, R.; Thompson, W. H.; Determinants of Activity at Human Toll-Like Receptors 7 and 8: Quantitative Structure–Activity Relationship (QSAR) of Diverse Heterocyclic Scaffolds. J. Med. Chem. 2014, 57, 7955–7970. DOI: 10.1021/jm500744f.
   PubMed Web of Science ®Google Scholar
• Li, J.-R.; Chen, X.; Shi, D.-X.; Ma, S.-L.; Li, Q.; Zhang, Q.; Tang, J.-H. A New and Facile Synthesis of Quinazoline-2,4(1H,3H)-Diones. Org. Lett. 2009, 11, 1193–1196. DOI: 10.1021/ol900093h.
   PubMed Web of Science ®Google Scholar
• Willis, M. C.; Snell, R. H.; Fletcher, A. J.; Woodward, R. L. Tandem Palladium-Catalyzed Urea Arylation−Intramolecular Ester Amidation: Regioselective Synthesis of 3-Alkylated 2, 4-Quinazolinediones. Org. Lett. 2006, 8, 5089–5091. DOI: 10.1021/ol062009x.
   PubMed Web of Science ®Google Scholar
• Wu, X.-W.; Yu, Z.-K. Metal and Phosgene-Free Synthesis of 1H-Quinazoline-2,4-Diones by Selenium-Catalyzed Carbonylation of o-Nitrobenzamides. Tetrahedron Lett. 2010, 51, 1500–1503. DOI: 10.1016/j.tetlet.2010.01.040.
   Google Scholar
• Jing, Y.-F.; Liu, R.-T.; Lin, Y.-H.; Zhou, X.-G. Lanthanide-Catalyzed Cyclocarbonylation and Cyclothiocarbonylation: A Facile Synthesis of Benzannulated 1,3-Diheteroatom Five- and Six-Membered Heterocycles. Sci. China Chem. 2014, 57, 1117–1125. DOI: 10.1007/s11426-014-5149-0.
   Web of Science ®Google Scholar
• Deng, X.-X.; Guo, L.; Xu, L.-L.; Zhen, X.-C.; Yu, K.-Q.; Zhao, W.-L.; Fu, W. Discovery of Novel Potent and Selective Ligands for 5-HT2A Receptor with Quinazoline Scaffold. Bioorg. Med. Chem. Lett. 2015, 25, 3970–3974. DOI: 10.1016/j.bmcl.2015.07.030.
   PubMedGoogle Scholar
• Sharafi-Kolkeshvandi, M.; Nikpour, F. A Facile and Convenient Approach for the One-Pot Synthesis of 2,4(1H,3H)-Quinazolinediones. Chinese Chem. Lett. 2012, 23, 431–433. DOI: 10.1016/j.cclet.2012.01.027.
   Web of Science ®Google Scholar
• Nikpour, F.; Havasi, F.; Arzegar, Z. Condensation Reaction of Ethyl 4-oxo-4H-benzo[d][1,3]oxazine-2-carboxylates with Potassium Cyanate: 2,4(1H,3H)-Quinazolinediones Synthesis. Heterocycles 2012, 85, 2745–2748. DOI: 10.3987/COM-12-12551.
   Web of Science ®Google Scholar