Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2013, Article ID 785930, 7 pages
http://dx.doi.org/10.1155/2013/785930
Research Article

Synthesis of Polyfunctionalized 4H-Pyrans

Department of Chemistry, North Eastern Hill University, Shillong 793022, India

Received 29 June 2012; Accepted 5 November 2012

Academic Editor: Joaquin Campos

Copyright © 2013 Manisha Bihani 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. B. Cornils, W. A. Herrmann, M. Muhler, and C. H. Wong, Catalysis from A to Z: A Concise Encyclopedia, Wiley-VCH, Weinheim, Germany, 2007.
  2. R. Sheldon, I. Arends, and U. Hanefeld, Green Chemistry and Catalysis, Wiley-VCH, Weinheim, Germany, 2007.
  3. P. W. N. M. van Leeuwen, Homogeneous Catalysis-Understanding the Art, Kluwer Academic, Dordrecht, The Netherlands, 2004.
  4. L. A. Thompson, “Recent applications of polymer-supported reagents and scavengers in combinatorial, parallel, or multistep synthesis,” Current Opinion in Chemical Biology, vol. 4, no. 3, pp. 324–337, 2000. View at Publisher · View at Google Scholar
  5. A. Nefzi, J. M. Ostresh, and R. A. Houghten, “The current status of heterocyclic combinatorial libraries,” Chemical Reviews, vol. 97, no. 2, pp. 449–472, 1997. View at Google Scholar · View at Scopus
  6. 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
  7. 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
  8. N. Martin, A. Martinez-Grau, C. Seoane, J. L. Marco, A. Albert, and F. H. Cano, “Michael addition of malononitrile to α-acetylcinnamamides,” Liebigs Annalen der Chemie, vol. 7, pp. 801–804, 1993. View at Google Scholar
  9. J. L. Wang, D. Liu, Z. J. Zhang et al., “Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells,” Proceedings of the National Academy of Sciences of the United States of America, vol. 97, no. 13, pp. 7124–7129, 2000. View at Publisher · View at Google Scholar
  10. A. Martinez-Grau and J. L. Marco, “Friedlander reaction on 2-amino-3-cyano-4H-pyrans: synthesis of derivatives of 4H-pyran[2,3-b]quinoline, new tacrine analogs,” Bioorganic & Medicinal Chemistry Letters, vol. 7, no. 24, pp. 3165–3170, 1997. View at Google Scholar
  11. 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
  12. D. Kumar, V. B. Reddy, S. Sharad, U. Dube, and S. Kapur, “A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes,” European Journal of Medicinal Chemistry, vol. 44, no. 9, pp. 3805–3809, 2009. View at Publisher · View at Google Scholar · View at Scopus
  13. C. S. Konkoy, D. B. Fick, S. X. Cai, N. C. Lan, and J. F. W. Keana, “Substituted 5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyrans and benzothiopyrans and the use thereof as potentiators of AMPA,” Chemical Abstracts, vol. 134, Article ID 29313a, 2001, International Application WO 00/75123 A1, 2000. View at Google Scholar
  14. N. Martin, C. Seoane, and J. L. Soto, “A convenient,one step synthesis of pyrano[2,3-b]pyridines,” Tetrahedron, vol. 44, no. 18, pp. 5861–5868, 1988. View at Google Scholar
  15. D. Heber and E. V. Stoyanov, “Synthesis of functionalized 4H-pyran and cyclohexanone derivatives via three-component reactions of dimethyl acetonedicarboxylate, aromatic aldehydes, and malononitrile,” Synthesis, no. 2, pp. 227–232, 2003. View at Google Scholar · View at Scopus
  16. Y. Peng and G. Song, “Amino-functionalized ionic liquid as catalytically active solvent for microwave-assisted synthesis of 4H-pyrans,” Catalysis Communications, vol. 8, no. 2, pp. 111–114, 2007. View at Publisher · View at Google Scholar
  17. Y. Peng, G. Song, and F. Huang, “Tetramethylguanidine-[bmim][BF4]. An efficient and recyclable catalytic system for one-pot synthesis of 4H-pyrans,” Monatshefte fur Chemie, vol. 136, no. 5, pp. 727–731, 2005. View at Publisher · View at Google Scholar · View at Scopus
  18. T. S. Jin, L. B. Liu, Y. Zhao, and T. S. Li, “Clean, one-pot synthesis of 4H-pyran derivatives catalyzed by hexadecyltrimethyl ammonium bromide in aqueous media,” Synthetic Communications, vol. 35, no. 14, pp. 1859–1863, 2005. View at Publisher · View at Google Scholar · View at Scopus
  19. N. S. Babu, N. Pasha, K. T. V. Rao, P. S. S. Prasad, and N. Lingaiah, “A heterogeneous strong basic Mg/La mixed oxide catalyst for efficient synthesis of polyfunctionalized pyrans,” Tetrahedron Letters, vol. 49, no. 17, pp. 2730–2733, 2008. View at Publisher · View at Google Scholar · View at Scopus
  20. M. M. Heravi, Y. S. Beheshtiha, Z. Pirnia, S. Sadjadi, and M. Adibi, “One-pot, three-component synthesis of 4H-pyrans using Cu(II) oxymetasilicate,” Synthetic Communications, vol. 39, no. 20, pp. 3663–3667, 2009. View at Publisher · View at Google Scholar · View at Scopus
  21. B. P. V. Lingaiah, G. V. Reddy, T. Yakaiah et al., “Efficient and convenient method for the synthesis of poly functionalised 4H-pyrans,” Synthetic Communications, vol. 34, no. 23, pp. 4431–4437, 2004. View at Publisher · View at Google Scholar · View at Scopus
  22. S. G. Zhang, S. F. Yin, Y. D. Wei, S. L. Luo, and C. T. Au, “Novel MgO–SnO2 solid superbase as a high-efficiency catalyst for one-pot solvent-free synthesis of polyfunctionalized 4H-pyran derivatives,” Catalysis Letters, vol. 142, no. 5, pp. 608–614, 2012. View at Publisher · View at Google Scholar
  23. U. R. Pratap, D. V. Jawale, P. D. Netankar, and R. A. Mane, “Baker’s yeast catalyzed one-pot three-component synthesis of polyfunctionalized 4H-pyrans,” Tetrahedron Letters, vol. 52, no. 44, pp. 5817–5819, 2011. View at Publisher · View at Google Scholar
  24. N. Srinivasan, A. Yurek-George, and A. Ganesan, “Rapid deprotection of N-Boc amines by TFA combined with freebase generation using basic ion-exchange resins,” Molecular Diversity, vol. 9, no. 4, pp. 291–293, 2005. View at Publisher · View at Google Scholar
  25. R. Ballini, L. Barboni, and P. Filippone, “Amberlyst A-21 an excellent heterogeneous catalyst for the conversion of carbonyl compounds to oximes,” Chemistry Letters, no. 5, pp. 475–476, 1997. View at Google Scholar
  26. R. Ballini, G. Bosica, and P. Forconi, “Nitroaldol (Henry) reaction catalyzed by Amberlyst A-21 as a far superior heterogeneous catalyst,” Tetrahedron, vol. 52, no. 5, pp. 1677–1684, 1996. View at Publisher · View at Google Scholar
  27. F. Bonfils, I. Cazaux, P. Hodge, and C. Caze, “Michael reactions carried out using a bench-top flow system,” Organic and Biomolecular Chemistry, vol. 4, no. 3, pp. 493–497, 2006. View at Publisher · View at Google Scholar
  28. S. M. Dhuri and V. V. Mahajani, “Studies in transesterification of ethylene carbonate to dimethyl carbonate over Amberlyst A-21 catalyst,” Journal of Chemical Technology and Biotechnology, vol. 81, no. 1, pp. 62–69, 2006. View at Publisher · View at Google Scholar · View at Scopus
  29. S. Mustafa, M. Khalid, A. Naeem, N. Rehana, and S. Murtaza, “Selective removal of chromates by macroporous exchanger Amberlyst A-21,” Environmental Technology, vol. 23, no. 5, pp. 583–590, 2002. View at Google Scholar