Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2014 (2014), Article ID 596171, 5 pages
http://dx.doi.org/10.1155/2014/596171
Research Article

Pentafluoropropionic Acid: An Efficient and Metal-Free Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives

1Department of Chemistry, Faculty of Sciences, Islamic Azad University, Tonekabon Branch, Tonekabon 46819-89711, Iran
2Young Researchers Club, Islamic Azad University, Tonekabon Branch, Tonekabon 46819-89711, Iran

Received 19 January 2014; Accepted 28 March 2014; Published 23 April 2014

Academic Editor: Mohamed Afzal Pasha

Copyright © 2014 Naser Montazeri 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. L. L. Andreani and E. Lapi, “On some new esters of coumarin-3-carboxylic acid wit balsamic and bronchodilator action,” Bollettino Chimico Farmaceutico, vol. 99, pp. 583–586, 1960. View at Google Scholar
  2. L. Bonsignore, G. Loy, D. Secci, and A. Calignano, “Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives,” European Journal of Medicinal Chemistry, vol. 28, no. 6, pp. 517–520, 1993. View at Publisher · View at Google Scholar · View at Scopus
  3. A. Saini, S. Kumar, and J. S. Sandhu, “A new LiBr-catalyzed, facile and efficient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j]xanthenes and tetrahydrobenzo[b]pyrans under solvent-free conventional and microwave heating,” Synlett, vol. 12, pp. 1928–1932, 2006. View at Google Scholar
  4. K. Singh, J. Singh, and H. Singh, “A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles,” Tetrahedron, vol. 52, no. 45, pp. 14273–14280, 1996. View at Publisher · View at Google Scholar · View at Scopus
  5. E. C. Witte, P. Neubert, and A. Roesch, “7-(piperazinyl propoxy)-2H-1-benzopyran-2-ones. Ger. Offen DE,” Chemical Abstracts, vol. 104, Article ID 224915f, 1986. View at Google Scholar
  6. X. S. Wang, D. Q. Shi, S. T. Tu, and C. S. Yao, “A convenient synthesis of 5-Oxo-5,6,7,8-tetrahydro-4 H-benzo-[b]-pyran derivatives catalyzed by KF-alumina,” Synthetic Communications, vol. 33, no. 1, pp. 119–126, 2003. View at Publisher · View at Google Scholar
  7. S. Hatakeyama, N. Ochi, H. Numata, and S. Takano, “A new route to substituted 3-methoxycarbonyldihydropyrans; enantioselective synthesis of (-)-methyl elenolate,” Journal of the Chemical Society, Chemical Communications, no. 17, pp. 1202–1204, 1988. View at Publisher · View at Google Scholar · View at Scopus
  8. G. R. Green, J. M. Evans, A. K. Vong, A. R. Katritzky, C. W. Rees, and E. F. Scriven, “Comprehensive heterocyclic chemistry II,” in Pyrans and Their Benzo Derivatives Synthesis, vol. 5, p. 469, Pergamon Press, Oxford, UK, 1995. View at Google Scholar
  9. D. Armesto, W. M. Horspool, N. Martin, A. Ramos, and C. Seoane, “Synthesis of cyclobutenes by the novel photochemical ring contraction of 4-substituted 2-amino-3,5-dicyano-6-phenyl-4H-pyrans,” Journal of Organic Chemistry, vol. 54, no. 13, pp. 3069–3072, 1989. View at Google Scholar · View at Scopus
  10. S. S. Katkar, M. K. Lande, B. R. Arbad, and S. T. Gaikwad, “A recyclable and highly effective ZnO-beta zeolite as a catalyst for one-pot three-component synthesis of tetrahydrobenzo[b]pyrans,” Chinese Journal of Chemistry, vol. 29, no. 1, pp. 199–202, 2011. View at Publisher · View at Google Scholar · View at Scopus
  11. I. Devi and P. J. Bhuyan, “Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions,” Tetrahedron Letters, vol. 45, no. 47, pp. 8625–8627, 2004. View at Publisher · View at Google Scholar · View at Scopus
  12. R. Hekmatshoar, S. Majedi, and K. Bakhtiari, “Sodium selenate catalyzed simple and efficient synthesis of tetrahydro benzo[b]pyran derivatives,” Catalysis Communications, vol. 9, no. 2, pp. 307–310, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. H. A. Oskooie, M. M. Heravi, N. Karimi, and M. Ebrahimzadeh, “Caro's acid-silica gel: an efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives,” Synthetic Communications, vol. 41, no. 3, pp. 436–440, 2011. View at Publisher · View at Google Scholar
  14. J. Zheng and Y. Q. Li, “One-pot synthesis of tetrahydrobenzo[b]pyran and dihydropyrano[c]chromene derivatives in aqueous media by using trisodium citrate as a green catalyst,” Scholars Research Library, vol. 3, no. 2, pp. 381–388, 2011. View at Google Scholar
  15. A. Davoodnia, S. Allameh, S. Fazli, and N. Tavakoli-Hoseini, “One-pot synthesis of 2-amino-3-cyano-4-arylsubstituted tetrahydrobenzo[b] pyrans catalysed by silica gel-supported polyphosphoric acid (PPA-SiO2) as an efficient and reusable catalyst,” Chemical Papers, vol. 65, no. 5, pp. 714–720, 2011. View at Publisher · View at Google Scholar · View at Scopus
  16. J. T. Li, W. Z. Xu, L. C. Yang, and T. S. Li, “One-pot synthesis of 2-amino-4-aryl-3-carbalkoxy-7,7-dimethyl-5,6,7,8-tetrahydrobenzo[b]pyran derivatives catalyzed by KF/Basic Al2O3 under ultrasound irradiation,” Synthetic Communications, vol. 34, no. 24, pp. 4565–4571, 2004. View at Publisher · View at Google Scholar
  17. D. Shi, J. Mou, Q. Zhuang, and X. Wang J, “One-pot synthesis of 2-amino-4-aryl-5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carbonitriles in aqueous media,” Journal of Chemical Research, vol. 2004, no. 12, pp. 821–823, 2004. View at Publisher · View at Google Scholar
  18. B. C. Ranu, S. Banetjee, and S. Roy, “A task specific basic ionic liquid, [bmIm]OH-promoted efficient, green and one- pot synthesis of tetrahydro-benzo[b]pyran derivatives,” Indian Journal of Chemistry B, vol. 47, no. 7, pp. 1108–1112, 2008. View at Google Scholar
  19. K. S. Niralwad, K. F. Shelke, S. S. Sadaphal, B. B. Shingate, and M. S. Shingare, “An efficient and green synthesis of tetrahydrobenzo[b]pyran derivatives catalysed by sodium hypochlorite by grinding,” Bulletin of the Catalysis Society of India, vol. 8, pp. 188–192, 2009. View at Google Scholar
  20. J. Azizian, A. Shameli, S. Balalaie et al., “The one-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives with 1,4-diazabicyclo[2.2.2]octane in aqueous media,” Oriental Journal of Chemistry, vol. 28, no. 1, pp. 327–332, 2012. View at Google Scholar
  21. A. M. Shestopalov, Y. M. Emelianova, and V. N. Nesterov, “One-step synthesis of substituted 2-amino-5,6,7,8-tetrahydro-4H-benzo[b]pyrans. Molecular and crystal structure of 2-amino-3-(2-methoxyethoxycarbonyl)-4-(2-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran,” Russian Chemical Bulletin International Edition, vol. 52, no. 5, pp. 1164–1171, 2003. View at Publisher · View at Google Scholar
  22. S. Rathod, B. Arbad, and M. Lande, “Preparation, characterization, and catalytic application of a nanosized Ce1MgxZr1-xO2 solid heterogeneous catalyst for the synthesis of tetrahydrobenzo[b]pyran derivatives,” Chinese Journal of Catalysis, vol. 31, no. 6, pp. 631–636, 2010. View at Publisher · View at Google Scholar
  23. R. L. Magar, P. B. Thorat, V. B. Jadhav, S. U. Takale, S. A. Patil, and R. P. Pawar, “Silica gel supported polyamine: a versatile catalyst for one pot synthesis of 2-amino-4H-chromene derivatives,” Journal of Molecular Catalysis A: Chemical, vol. 374-375, pp. 118–124, 2013. View at Publisher · View at Google Scholar
  24. N. Azizi, S. Dezfooli, M. Khajeh, and M. Mahmoudi Hashemi, “Efficient deep eutectic solvents catalyzed synthesis of pyran and benzopyran derivatives,” Journal of Molecular Liquids, vol. 186, pp. 76–80, 2013. View at Publisher · View at Google Scholar
  25. S. Khaksar, A. Rouhollahpour, and S. Mohammadzadeh Talesh, “A facile and efficient synthesis of 2-amino-3-cyano-4H-chromenes and tetrahydrobenzo[b]pyrans using 2,2,2-trifluoroethanol as a metal-free and reusable medium,” Journal of Fluorine Chemistry, vol. 141, pp. 11–15, 2012. View at Publisher · View at Google Scholar
  26. S. Balalaie, M. Sheikh-Ahmadi, and M. Bararjanian, “Tetra-methyl ammonium hydroxide: an efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media,” Catalysis Communications, vol. 8, no. 11, pp. 1724–1728, 2007. View at Publisher · View at Google Scholar · View at Scopus
  27. K. A. Undale, Y. Park, K. Park, D. H. Dagade, and D. M. Pore, “A revisit to the hantzsch reaction: unexpected formation of tetrahydro-benzo[ b ]pyrans beyond polyhydroquinolines,” Synlett, no. 6, pp. 791–796, 2011. View at Publisher · View at Google Scholar · View at Scopus
  28. S. Gurumurthi, V. Sundari, and R. Valliappan, “An efficient and convenient approach to synthesis of tetrahydrobenzo[b] pyran derivatives using tetrabutylammonium bromide as catalyst,” E-Journal of Chemistry, vol. 6, supplement 1, pp. S466–S472, 2009. View at Google Scholar · View at Scopus
  29. N. Montazeri, S. Khaksar, A. Nazari, S. S. Alavi, S. M. Vahdat, and M. Tajbakhsh, “Pentafluorophenylammonium triflate (PFPAT): an efficient, metal-free and reusable catalyst for the von Pechmann reaction,” Journal of Fluorine Chemistry, vol. 132, no. 7, pp. 450–452, 2011. View at Publisher · View at Google Scholar · View at Scopus
  30. N. Montazeri, K. Pourshamsian, S. Yosefiyan, and S. Momeni, “Pentafluorophenylammonium triflate-CuCl2: a mild, efficient and reusable heterogeneous catalyst system for facile synthesis of 4(3H)-quinazolinones under solvent-free conditions,” Journal of Chemical Sciences, vol. 124, no. 4, pp. 883–887, 2012. View at Publisher · View at Google Scholar
  31. N. Montazeri and S. Mahjoob, “Highly efficient and easy synthesis of 2,4,6-triarylpyridines catalyzed by pentafluorophenylammonium triflate (PFPAT) as a new recyclable solid acid catalyst in solvent-free conditions,” Chinese Chemical Letters, vol. 23, no. 4, pp. 419–422, 2012. View at Publisher · View at Google Scholar
  32. N. Montazeri and K. Rad-Moghadam, “An expeditious and one-pot synthesis of unsymmetrical 2,5-disubstituted-1,3,4-oxadiazoles under microwave irradiation and solvent-free conditions,” Chinese Chemical Letters, vol. 19, no. 10, pp. 1143–1146, 2008. View at Publisher · View at Google Scholar