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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 24
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Synthetic Communications Reviews

Synthesis and biological application of pyranopyrimidine derivatives catalyzed by efficient nanoparticles and their nucleoside analogues

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Pages 3560-3572 | Received 02 Jul 2019, Published online: 04 Nov 2019

References

  • Ghasemzadeh, M. A.; Safaei-Ghomi, J.; Zahedi, S. Fe3O4 Nanoparticles: A Highly Efficient and Easily Reusable Catalyst for the One-Pot Synthesis of Xanthene Derivatives under Solvent-Free Conditions. J. Serb. Chem. Soc. 2013, 78, 769–779. DOI: 10.2298/JSC120624156G.
  • Jiang, H.; Gai, L.; Tian, Y. Altervalent Cation-Doped MCM-41 Supported Palladium Catalysts and Their Catalytic Properties. J. Serb. Chem. Soc. 2011, 76, 923–932. DOI: 10.2298/JSC100227073J.
  • Furuya, S.; Ohtaki, T. Eur. Pat. Appl. EP. 608565, 1994. Chem. Abstr. 1994, 121, 205395.
  • Grivsky, E. M.; Lee, S.; Sigel, C. W.; Duch, D. S.; Nichol, C. A. Synthesis and Antitumor Activity of 2,4-Diamino-6-(2,5-Dimethoxybenzyl)-5-Methylpyrido[2,3-d]Pyrimidine. J. Med. Chem. 1980, 23, 327–329. DOI: 10.1021/jm00177a025.
  • Heber, D.; Heers, C.; Ravens, U. Positive Inotropic Activity of 5-Amino-6-Cyano-1,3-Dimethyl-1,2,3,4-Tetrahydropyrido[2,3-d]Pyrimidine-2,4-Dione in Cardiac Muscle from guinea-Pig and Man. Part 6: Compounds with Positive Inotropic Activity. Die Pharmazie 1993, 48, 537–541.
  • Ahluwalia, V. K.; Batla, R.; Khurana, A.; Kumar, R. ChemInform Abstract: Synthesis of 1,3‐Diaryl‐7,7‐Diethyl‐5‐Methyl‐4‐Oxo‐2‐Thioxo‐1,2,3,4‐Tetrahydro‐7H‐Pyrano(2,3‐d)Pyrimidines. Chem. Inform. 1991, 22, 164. DOI: 10.1002/chin.199122164.
  • Stevens, P. D.; Fan, J.; Gardimalla, H. M.; Yen, M.; Gao, Y. Superparamagnetic Nanoparticle-Supported Catalysis of Suzuki Cross-Coupling Reactions. Org. Lett. 2005, 7, 2085–2088. DOI: 10.1021/ol050218w.
  • Lü, H. Y.; Yang, S. H.; Deng, J.; Zhang, Z. H. Magnetic Fe3O4 Nanoparticles as New, Efficient, and Reusable Catalysts for the Synthesis of Quinoxalines in Water. Aust. J. Chem. 2010, 63, 1290–1296. DOI: 10.1071/CH09532.
  • Roopan, S. M.; Khan, F. R. N.; Mandal, B. K. Fe Nano Particles Mediated C–N Bond-Forming Reaction: Regioselective Synthesis of 3-[(2-Chloroquinolin-3-yl)Methyl]Pyrimidin-4(3H)Ones. Tetrahedron Lett. 2010, 51, 2309–2311. DOI: 10.1016/j.tetlet.2010.02.128.
  • Zeng, T.; Chen, W. W.; Cirtiu, C. M.; Moores, A.; Song, G.; Li, C. J. Fe3O4 Nanoparticles: A Robust and Magnetically Recoverable Catalyst for Three-Component Coupling of Aldehyde, Alkyne and Amine. Green Chem. 2010, 12, 570–573. DOI: 10.1039/b920000b.
  • Polshettiwar, V.; Varma, R. S. Nano-Organocatalyst: Magnetically Retrievable Ferrite-Anchored Glutathione for Microwave-Assisted Paal–Knorr Reaction, aza-Michael Addition, and Pyrazole Synthesis. Tetrahedron 2010, 66, 1091–1097. DOI: 10.1016/j.tet.2009.11.015.
  • Seyyedi, N.; Shirini, F.; Langarudi, M. S. N. DABCO-Based Ionic Liquids: Green and Recyclable Catalysts for the Synthesis of Barbituric and Thiobarbituric Acid Derivatives in Aqueous Media. RSC Adv. 2016, 6, 44630–44640. DOI: 10.1039/C6RA05878G.
  • Sadeghi, B.; Bouslik, M.; Shishehbore, A. M. Nano-Sawdust-OSO3H as a New, Cheap and Effective Nanocatalyst for One-Pot Synthesis of Pyrano[2,3-d]Pyrimidines. J. Iran. Chem. Soc. 2015, 12, 1801–1808. DOI: 10.1007/s13738-015-0655-3.
  • Sabour, B.; Peyrovi, M. H.; Hajimohammadi, M. Al-HMS-20 Catalyzed Synthesis of Pyrano[2,3-d]Pyrimidines and Pyrido[2,3-d]Pyrimidines via Three-Component Reaction. Res. Chem. Intermed. 2015, 41, 1343–1350. DOI: 10.1007/s11164-013-1277-y.
  • Shaabani, A.; Seyyedhamzeh, M.; Maleki, A.; Rezazadeh, F.; Behnam, M. New One-Pot Four-Component Synthesis of Disubstituted Pyrido[2,3-d]Pyrimidine-6-Carboxamide Derivatives. J. Comb. Chem. 2009, 11, 375–377. DOI: 10.1021/cc800189j.
  • Moustafa, A. H.; Saad, H. A.; Shehab, W. S.; El-Mobayed, M. M. Synthesis of Some New Pyrimidine Derivatives of Expected Antimicrobial Activity. Phosphorus, Sulfur, and Silicon and the Rel. Elem. 2007, 183, 115–135. DOI: 10.1080/10426500701557286.
  • Shehab, W. S. Synthesis of Tetrahydropyrimidine Derivatives and Its Glycosides. COC. 2009, 13, 1848–1851. DOI: 10.2174/138527209789630451.
  • Shehab, W. S.; Mohamed, E. K. Synthesis of Some New S-Glycosyl Pyrimidine and Condensed Pyrimidine Derivatives. Eur. J. Chem. 2012, 3, 241–246. DOI: 10.5155/eurjchem.3.2.241-246.597.
  • Shehab, W. S.; El-Shwiniy, W. H. Nanoparticles of Manganese Oxides as Efficient Catalyst for the Synthesis of Pyrano[2,3-d]Pyrimidine Derivatives and Their Complexes as Potent Protease Inhibitors. J. Iran. Chem. Soc. 2018, 15, 431–443. DOI: 10.1007/s13738-017-1244-4.
  • Chate, A. V.; Dongre, R. M.; Khaire, M. K.; Bondle, G. M.; Sangshetti, J. N.; Damale, M. β-CD-Catalyzed Multicomponent Domino Reaction: Synthesis, Characterization, in Silico Molecular Docking and Biological Evaluation of Pyrano[2,3-d]-Pyrimidinone Derivatives. Res. Chem. Intermed. 2018, 44, 6119–6136. DOI: 10.1007/s11164-018-3479-9.
  • Krim, J.; Sillahi, B.; Taourirte, M.; Rakib, E. M.; Engels, J. W. Microwave-assisted click chemistry: synthesis of mono and bis-1,2,3-triazole acyclonucleoside analogues of ACV via copper(I)-catalyzed cycloaddition (09-4115AP). Arkivoc 2009, 2009, 142–152.
  • El-Sayed, H. A.; Moustafa, A. H.; Haikal, A. Z.; Abdou, I. M.; El-Ashry, E. S. H. Synthesis and Evaluation of Antimicrobial Activity of Some Pyrimidine Glycosides. Nucleos. Nucleot. Nucl. Acids 2008, 27, 1061–1071. DOI: 10.1080/15257770802271805.
  • Eweiss, N. F.; Osman, A. Synthesis of Heterocycles. Part II. New Routes to Acetylthiadiazolines and Alkylazothiazoles. J. Heterocycl. Chem. 1980, 17, 1713–1717. DOI: 10.1002/jhet.5570170814.
  • Bauer, A. W.; Kirby, W. M. M.; Sherris, J. C.; Turck, M. Antibiotic Susceptibility Testing by a Standardized Single Disk Method. Am. J. Clin. Pathol. 1966, 45, 493–496. DOI: 10.1093/ajcp/45.4_ts.493.
  • Adeniyi, B. A.; Odelola, H. A.; Oso, B. A. Antimicrobial Potentials of Diospyros Mespiliformis (Ebenaceae). Afr. J. Med. Med. Sci. 1996, 25, 221–224.
  • Hindler, A. J.; Jorgensen, J. H.; Mahon, C. R.; Manuselis, G. Jr. Textbook of Diagnostic Microbiology; WB Saunders: Philadelphia, PA, 1995; pp. 63–64.

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