10.1007/s40089-015-0145-8

Efficient one-pot synthesis of pyrido[2,3-d]pyrimidines catalyzed by nanocrystalline MgO in water

HTML PDF
  • Amaneh Mossafaii Rad1,
  • Masoud Mokhtary*1,
  1. Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, IR
Cover Image

Published in Issue 2015-04-15

How to Cite

Rad, A. M., & Mokhtary, M. (2015). Efficient one-pot synthesis of pyrido[2,3-d]pyrimidines catalyzed by nanocrystalline MgO in water. International Nano Letters, 5(2 (June 2015). https://doi.org/10.1007/s40089-015-0145-8
Crossref
Scopus
Google Scholar
Europe PMC

HTML views: 28

PDF views: 135

Abstract

Abstract The direct three-component condensation of 6-aminouracil, 6-amino-2-thiouracil or 6-amino-1,3-dimethyluracil, with arylaldehydes and malononitrile to generate a series of pyrido[2,3- d ]pyrimidine derivatives has been carried out over nanocrystalline MgO with high efficiency in water as a green solvent at 80 °C. The morphology and structure of the nanocrystalline MgO were characterized by scanning electron microscopy, transmission electron microscopy and X-ray diffraction. The results confirmed the nanocrystalline MgO particle size is approximately 50 nm. This methodology offers significant improvements for the synthesis of pyrido[2,3- d ]pyrimidine derivatives with regard to the yield of products, simplicity in operation, and green aspects by avoiding toxic catalysts and solvents.

Keywords

  • Aminouracils,
  • Pyrido[2,3-d]pyrimidines,
  • Nanocrystalline MgO,
  • Multicomponent reaction
HTML PDF

References

  1. Montreo et al. (2010) In situ studies structure-reactivity relations in synthesis of biodiesel over nanocrystalline MgO https://doi.org/10.1016/j.cej.2009.12.035
  2. Narayanan and Ei-Sayed (2004) Shape dependent catalytic activity of platinum nanoparticles in colloidal solution https://doi.org/10.1021/nl0495256
  3. Shi et al. (2007) Tuning catalytic activity between homogenous and heterogeneous catalysis improved activity and selectivity of free nano-Fe2O3 in selective oxidations https://doi.org/10.1002/anie.200703418
  4. Grivaky et al. (1980) Synthesis and antitumor activity of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido[2,3-d]pyrimidine https://doi.org/10.1021/jm00177a025
  5. Furuya, S., Ohtaki, T.: Pyridopyrimidine derivatives, their production and use, Eur. Pat. Appl. EP. 608565 (1994)
  6. Heber et al. (1993) 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
  7. DeGraw et al. (1992) Synthesis and antifolate properties of 5,10-ethano-5,10-dideazaaminopterin https://doi.org/10.1021/jm00080a017
  8. Bradshaw and Hutchinson (1977) 5-Substituted pyrimidine nucleosides and nucleotides https://doi.org/10.1039/cs9770600043
  9. Quiroga et al. (2001) Synthesis and structural analysis of 5-cyanodihydropyrazolo[3,4-b]pyridines https://doi.org/10.1002/jhet.5570380108
  10. Thakur, A.J., Saikia, P., Prajapati, D., Sandhu, J.S.: Studies on 6-[(dimethylamino) methylene]aminouracils: a facile one-pot synthesis of pyrimido[4,5-d]pyrimidines and pyrido[2,3-d]pyrimidines, Synlett, 1299 (2001)
  11. Perez-Perez, M.J., Pretago, E.M., Jimeno, M.L., Camarasa M.J.: A new and efficient one-pot synthesis of pyrido[2,1-
  12. f
  13. ]purine-2,4-diones starting from 6-aminouracil derivatives, Synlett 155 (2002)
  14. Bhuyan et al. (1990) Studies on uracils. 10. A facile one-pot synthesis of pyrido[2,3-d]- and pyrazolo[3,4-d]pyrimidines https://doi.org/10.1021/jo00289a033
  15. Muller et al. (1997) Synthesis and structure-activity relationships of 3,7-dimethyl-1-propargylxanthine derivatives, A2A-selective adenosine receptor antagonists https://doi.org/10.1021/jm970515+
  16. Hirota et al. (1994) Novel synthesis of pyrido[3,4-d]pyrimidines, pyrido[2,3-d]pyrimidines, and quinazolines via palladium-catalyzed oxidative coupling https://doi.org/10.3987/COM-93-S99
  17. Srivastava, P., Saxena, A.S., Ram, V.J.: An elegant approach towards the regioselective synthesis of deazalumazines through nucleophile induced ring transformation reactions of 6-aryl-3-cyano-4-methylthio-2
  18. H
  19. -pyran-2-ones, Synthesis 541 (2000)
  20. Wang et al. (2004) KF-alumina catalyzed one-pot synthesis of pyrido[2,3-d]pyrimidine derivatives https://doi.org/10.1081/SCC-200039392
  21. Samai et al. (2011) l-Proline catalyzed synthesis of densely functionalized pyrido[2,3-d]pyrimidines via three-component one-pot domino Knoevenagel aza-Diels–Alder reaction https://doi.org/10.1016/j.tet.2011.06.051
  22. Yang et al. (2012) Syntheses and cell-based phenotypic screen of novel 7-Amino pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives as potential antiproliferative agents https://doi.org/10.3390/molecules17032351
  23. Abdolmohammadi and Balalaie (2012) An efficient synthesis of pyrido[2,3-d]pyrimidine derivatives via one-pot three-component reaction in aqueous media https://doi.org/10.4236/ijoc.2012.21002
  24. Hussein, E.M.: Enviro-economic, ultrasound-assisted one-pot, three-component synthesis of pyrido[2,3-
  25. d
  26. ]pyrimidines in aqueous medium. Z. Naturforsch.
  27. 67b
  28. , 231 (2012)
  29. Karmakar and Banerji (2011) A competent pot and atom-efficient synthesis of Betti bases over nanocrystalline MgO involving a modified Mannich type reaction https://doi.org/10.1016/j.tetlet.2011.07.075
  30. Safari et al. (2013) Practical, ecofriendly, and highly efficient synthesis of 2-amino-4H-chromenes using nanocrystalline MgO as a reusable heterogeneous catalyst in aqueous media https://doi.org/10.1016/j.jtusci.2013.03.001