Table of Contents
Organic Chemistry International
Volume 2014 (2014), Article ID 210327, 10 pages
http://dx.doi.org/10.1155/2014/210327
Research Article

Kinetic and Mechanistic Investigation of Pyrano[2,3-d]pyrimidine Formation in the Presence of Catalyst under Novel One-Pot Three-Component Reaction

Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan 76177-48414, Iran

Received 3 February 2014; Revised 25 February 2014; Accepted 25 February 2014; Published 11 May 2014

Academic Editor: Ashraf Aly Shehata

Copyright © 2014 Sayyed Mostafa Habibi-Khorassani et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. C. C. A. Cariou, G. J. Clarkson, and M. Shipman, “Rapid synthesis of 1,3,4,4-tetrasubstituted β-lactams from methyleneaziridines using a four-component reaction,” Journal of Organic Chemistry, vol. 73, no. 24, pp. 9762–9764, 2008. View at Publisher · View at Google Scholar · View at Scopus
  2. S. M. Kupchan, Y. Komoda, W. A. Court et al., “Maytansine, a novel antileukemic ansa macrolide from Maytenus ovatus,” Journal of the American Chemical Society, vol. 94, no. 4, pp. 1354–1356, 1972. View at Google Scholar · View at Scopus
  3. R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, and T. A. Keating, “Multiple-component condensation strategies for combinatorial library synthesis,” Accounts of Chemical Research, vol. 29, no. 3, pp. 123–131, 1996. View at Publisher · View at Google Scholar
  4. G. Ren, J. Zhang, Z. Duan, M. Cui, and Y. Wu, “A simple and economic synthesis of propargylamines by cuI-catalyzed three-component coupling reaction with succinic acid as additive,” Australian Journal of Chemistry, vol. 62, no. 1, pp. 75–81, 2009. View at Publisher · View at Google Scholar · View at Scopus
  5. C. Mukhopadhyay, A. Datta, and R. J. Butcher, “Highly efficient one-pot, three-component Mannich reaction catalysed by boric acid and glycerol in water with major 'syn' diastereoselectivity,” Tetrahedron Letters, vol. 50, no. 29, pp. 4246–4250, 2009. View at Publisher · View at Google Scholar · View at Scopus
  6. C. Mukhopadhyay, P. K. Tapaswi, and M. G. B. Drew, “Room temperature synthesis of tri-, tetrasubstituted imidazoles and bis-analogues by mercaptopropylsilica (MPS) in aqueous methanol: application to the synthesis of the drug trifenagrel,” Tetrahedron Letters, vol. 51, no. 30, pp. 3944–3950, 2010. View at Publisher · View at Google Scholar · View at Scopus
  7. Y. Morianka and K. J. Takahashi, Japanese Kokai, vol. 17, p. 498, 1977.
  8. J.-B. Montandon, F. J. Zijlstra, J. H. P. Wilson, E. M. Grandjean, and L. Cicurel, “In-vitro versus in-vivo activities of new 5-lipoxygenase inhibitors with antiinflammatory activity,” International Journal of Tissue Reactions, vol. 11, no. 3, pp. 107–112, 1989. View at Google Scholar · View at Scopus
  9. G. T. Brooks, “The effect of some furochromene and benzochromene analogues of 2,2-dimethyl-7-methoxychromene (precocene I) and benzofuran precursors on Oncopeltus fasciatus (dallas) and Locusta migratoria migratorioides (R&F),” Journal of Pesticide Science, vol. 22, pp. 41–50, 1998. View at Publisher · View at Google Scholar
  10. T. Hyana and H. Saimoto, “Preparation of (furanyl) pentenglchromene derivatives as anticancer agents,” Jpn Patent JP 621812768, 1987.
  11. E. A. A. Hafez, M. H. Elnagdi, A. G. Ali Elagamey, and F. M. A. A. El-Taweel, “Nitriles in heterocyclic synthesis: novel synthesis of benzo[c]-coumarin and of benzo[c]pyrano[3,2-c]quinoline derivatives,” Heterocycles, vol. 26, no. 4, pp. 903–907, 1987. View at Google Scholar · View at Scopus
  12. F. M. Abdel-Galil, B. Y. Riad, S. M. Sherif, and M. H. Elnagdi, “Activated nitriles in heterocyclic synthesis: a novel synthesis of 4-azoloyl-2-aminoquinolines,” Chemistry Letters, vol. 11, no. 8, pp. 1123–1126, 1982. View at Publisher · View at Google Scholar
  13. M. EI-Agrody, Journal of Chemical Research, p. 280, 1994.
  14. M. Bararjanian, S. Balalaie, B. Movassagh, and A. M. Amani, “One-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives catalyzed by L-proline in aqueous media,” Journal of the Iranian Chemical Society, vol. 6, no. 2, pp. 436–442, 2009. View at Google Scholar · View at Scopus
  15. M. Kidwai and S. Saxena, “Convenient preparation of pyrano benzopyranes in aqueous media,” Synthetic Communications, vol. 36, no. 18, pp. 2737–2742, 2006. View at Publisher · View at Google Scholar · View at Scopus
  16. M. M. Heravi, B. A. Jani, F. Derikvand, F. F. Bamoharram, and H. A. Oskooie, “Three component, one-pot synthesis of dihydropyrano[3,2-c]chromene derivatives in the presence of H6P2W18O62· 18H2O as a green and recyclable catalyst,” Catalysis Communications, vol. 10, no. 3, pp. 272–275, 2008. View at Publisher · View at Google Scholar · View at Scopus
  17. A. T. Khan, M. Lal, S. Ali, and M. M. Khan, “One-pot three-component reaction for the synthesis of pyran annulated heterocyclic compounds using DMAP as a catalyst,” Tetrahedron Letters, vol. 52, no. 41, pp. 5327–5332, 2011. View at Publisher · View at Google Scholar · View at Scopus
  18. S. Balalaie, S. Abdolmohammadi, H. R. Bijanzadeh, and A. M. Amani, “Diammonium hydrogen phosphate as a versatile and efficient catalyst for the one-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives in aqueous media,” Molecular Diversity, vol. 12, no. 2, pp. 85–91, 2008. View at Publisher · View at Google Scholar · View at Scopus
  19. N. Hazeri, M. T. Maghsoodlou, S. M. Habibi-Khorassani, J. Aboonajmi, M. Lashkari, and S. S. Sajadikhah, “A green protocol for one-pot three-component synthesis of α-amino phosphonates catalyzed by succinic acid,” Research on Chemical Intermediates. View at Publisher · View at Google Scholar
  20. N. Hazeri, M. T. Maghsoodlou, S. M. Habibi-Khorassani, J. Aboonajmi, and S. S. Sajadikhah, “Fe(NO3)3· 9H2O as efficient catalyst for one-pot synthesis of highly functionalized piperidines,” Journal of the Chinese Chemical Society, vol. 60, no. 4, pp. 355–358, 2013. View at Publisher · View at Google Scholar
  21. M. Lashkari, N. Hazeri, M. T. Maghsoodlou et al., “Synthesis and crystal structure study of diethyl aryl(benzo[d]thiazol-2-ylamino)methyl phosphonates,” Heteroatom Chemistry, vol. 24, no. 1, pp. 58–65, 2013. View at Publisher · View at Google Scholar
  22. M. R. Mousavi, J. Aboonajmi, M. T. Maghsoodlou, N. Hazeri, S. M. Habibi-Khorassani, and M. Safarzaei, “La(NO3)3 . 6H2O catalyzed one-pot highly diastereoselective synthesis of functionalized piperidines,” Letters in Organic Chemistry, vol. 10, no. 3, pp. 1570–1786, 2013. View at Publisher · View at Google Scholar
  23. N. Hazeri, M. T. Maghsoodlou, M. R. Mousavi, J. Aboonajmi, and M. Safarzaei, “Potassium sodium tartrate as a versatile and efficient catalyst for the one-pot synthesis of pyran annulated heterocyclic compounds in aqueous media,” Research on Chemical Intermediates. View at Publisher · View at Google Scholar
  24. O. J. Nielsen, J. Sehested, S. Langer, E. Ljungström, and I. Wängberg, “UV absorption spectra and kinetics for alkyl and alkyl peroxy radicals originating from di-tert-butyl ether,” Chemical Physics Letters, vol. 238, no. 4-6, pp. 359–364, 1995. View at Google Scholar · View at Scopus
  25. S. Langer, E. Ljungström, T. Ellermann, O. J. Nielsen, and J. Sehested, “Pulse radiolysis study of reactions of alkyl and alkylperoxy radicals originating from methyl tert-butyl ether in the gas phase,” Chemical Physics Letters, vol. 240, no. 5-6, pp. 499–505, 1995. View at Google Scholar · View at Scopus
  26. V. V. Ivanov and C. Decker, “Kinetic study of photoinitiated frontal polymerization,” Polymer International, vol. 50, no. 1, pp. 113–118, 2001. View at Publisher · View at Google Scholar
  27. P. C. Fung, K. M. Sin, and S. M. Tsui, “Decolorisation and degradation kinetics of reactive dye wastewater by a UV/ultrasonic/peroxide system,” Journal of the Society of Dyers and Colourists, vol. 116, no. 5-6, pp. 170–173, 2000. View at Google Scholar · View at Scopus
  28. F. Misiti, M. Castagnola, C. Zuppi, B. Giardina, and I. Messana, “Role of ergothioneine on S-nitrosoglutathione catabolism,” Biochemical Journal, vol. 356, no. 3, pp. 799–804, 2001. View at Publisher · View at Google Scholar · View at Scopus
  29. M. Shaharaki, S. M. Habibi-Khorassani, A. Ebrahimi, M. T. Maghsoodlou, and A. Pakanahad, “Theoretical, kinetic and mechanistic studies of the reaction between dialkyl acetylenedicarboxylates, triphenylphosphine and pyrrole in organic solvents,” Progress in Reaction Kinetics and Mechanism, vol. 37, no. 4, pp. 321–343, 2012. View at Publisher · View at Google Scholar
  30. S. M. Habibi-Khorassani, M. T. Maghsoodlou, M. Zakarianezhad, M. Nassiri, M. A. Kazemian, and P. Karimi, “A facile synthesis of stable phosphorus ylides derived from 3,6-dibromocarbazole and kinetic investigation of the reactions by UV spectrophotometry technique,” Heteroatom Chemistry, vol. 19, no. 7, pp. 723–732, 2008. View at Publisher · View at Google Scholar · View at Scopus
  31. S. M. Habibi-Khorassani, A. Ebrahimi, M. T. Maghsoodlou et al., “Theoretical study, an efficient synthesis route to, and kinetic investigation of, stable phosphorus ylides derived from benzamide,” Progress in Reaction Kinetics and Mechanism, vol. 34, no. 3, pp. 261–288, 2009. View at Publisher · View at Google Scholar
  32. S. M. Habibi Khorassani, M. T. Maghsoodlou, A. Ebrahimi, M. Zakarianejad, and M. Fattahi, “Kinetics and mechanism of the reactions between triphenylphosphine, dialkyl acetylenedicarboxilates and a NH-acid, pyrazole, by UV spectrophotometry,” Journal of Solution Chemistry, vol. 36, no. 9, pp. 1117–1127, 2007. View at Publisher · View at Google Scholar · View at Scopus
  33. S. M. Habibi-Khorassani, M. T. Maghsoodlou, E. Aghdaei, and M. Shahraki, “1H NMR technique for kinetic investigation of equilibrium between the Z- and E-isomers in a stable phosphorus ylide involving a 2-indolinone,” Progress in Reaction Kinetics and Mechanism, vol. 37, no. 3, pp. 301–310, 2012. View at Publisher · View at Google Scholar
  34. M. A. Kazemian, P. Karimi, S. M. Habibi-Khorassani, A. Ebrahimi, M. T. Maghsoodlou, and F. J. Milani, “Synthesis of stable phosphorus ylides from 6-chloro-2-benzoxazolinone and kinetic investigation of the reactions by uv spectrophotometry,” Progress in Reaction Kinetics and Mechanism, vol. 34, no. 1, pp. 77–96, 2009. View at Publisher · View at Google Scholar · View at Scopus
  35. S. M. Habibi Khorassani, M. T. Maghsoodlou, A. Ebrahimi, M. Zakarianejad, P. Mojhammadzadeh, and M. Shahraki, “Kinetic study and mechanism investigation of the reactions between triphenylphosphine, dialkyl acetylene dicarboxylates and NH-acid such as Harman,” Oriental Journal of Chemistry, vol. 24, no. 1, pp. 73–82, 2008. View at Google Scholar · View at Scopus
  36. S. M. Habibi-Khorassani, A. Ebrahimi, M. T. Maghsoodlou, M. Zakarianezhad, H. Ghasempour, and Z. Ghahghayi, “Theoretical, nmr study, kinetics and a mechanistic investigation of the reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and 2-aminothiophenol,” Current Organic Chemistry, vol. 15, no. 6, pp. 942–952, 2011. View at Publisher · View at Google Scholar · View at Scopus
  37. S. Mashkouri and M. R. Naimi-Jamal, “Mechanochemical solvent-free and catalyst-free one-pot synthesis of pyrano[2,3-d]pyrimidine-2,4(1H,3H)-diones with quantitative yields,” Molecules, vol. 14, no. 1, pp. 474–479, 2009. View at Publisher · View at Google Scholar · View at Scopus
  38. L. M. Schwartz and R. I. Gelb, “Alternative method of analyzing first-order kinetic data,” Analytical Chemistry, vol. 50, no. 11, pp. 1592–1594, 1978. View at Google Scholar · View at Scopus
  39. G. Lente, I. Fábián, and A. J. Poë, “A common misconception about the Eyring equation,” New Journal of Chemistry, vol. 29, no. 6, pp. 759–760, 2005. View at Publisher · View at Google Scholar · View at Scopus
  40. J. H. Espenson, Chemical Kinetics and Reaction Mechanisms, McGraw-Hill, New York, NY, USA, 2nd edition, 1995.
  41. A. J. Poe, “Mechanisms of inorganic 32 and organometallic reaction,” in Mechanisms of Inorganic and Organometallic Reaction, M. V. Twigg, Ed., vol. 8, chapter 10, p. 220, Plenum Prss, New York, NY, USA, 1994. View at Google Scholar