Table of Contents
ISRN Organic Chemistry
Volume 2013 (2013), Article ID 793159, 6 pages
http://dx.doi.org/10.1155/2013/793159
Research Article

Nanorod-Shaped Basic Catalyzed N,N-Diformylation of Bisuracil Derivatives: A Greener “NOSE” Approach

Department of Chemical Sciences, Tezpur University (A Central University), Napaam, Assam 784028, India

Received 14 May 2013; Accepted 10 June 2013

Academic Editors: R. Pohl and D. Sémeril

Copyright © 2013 Vijay K. Das and Ashim J. Thakur. 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. D. Astruc, F. Lu, and J. R. Aranzaes, “Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis,” Angewandte Chemie—International Edition, vol. 44, no. 48, pp. 7852–7872, 2005. View at Publisher · View at Google Scholar · View at Scopus
  2. J. Grunes, J. Zhu, and G. A. Somorjai, “Catalysis and nanoscience,” Chemical Communications, vol. 9, no. 18, pp. 2257–2260, 2003. View at Google Scholar · View at Scopus
  3. J. Rautio, P. Perämäki, J. Honkamo, and H. Jantunen, “Effect of synthesis method variables on particle size in the preparation of homogeneous doped nano ZnO material,” Microchemical Journal, vol. 91, no. 2, pp. 272–276, 2009. View at Publisher · View at Google Scholar · View at Scopus
  4. M. T. Reetz and E. Westermann, “Phosphane-free palladium-catalyzed coupling reactions: the decisive role of Pd nanoparticles,” Angewandte Chemie—International Edition, vol. 39, no. 1, pp. 165–168, 2000. View at Publisher · View at Google Scholar
  5. C. Ramarao, S. V. Ley, S. C. Smith, I. M. Shirley, and N. DeAlmeida, “Encapsulation of palladium in polyurea microcapsules,” Chemical Communications, no. 10, pp. 1132–1133, 2002. View at Google Scholar · View at Scopus
  6. J. A. Gladysz, “Recoverable catalysts. Ultimate goals, criteria of evaluation, and the green chemistry interface,” Pure and Applied Chemistry, vol. 73, no. 8, pp. 1319–1324, 2001. View at Google Scholar · View at Scopus
  7. J. A. Gladysz, “Introduction: recoverable catalysts and reagents—perspective and prospective,” Chemical Reviews, vol. 102, no. 10, pp. 3215–3216, 2002. View at Publisher · View at Google Scholar · View at Scopus
  8. G. Pacchioni, “Quantum chemistry of oxide surfaces: from CO chemisorption to the identification of the structure and nature of point defects on MgO,” Surface Review and Letters, vol. 7, no. 3, pp. 277–306, 2000. View at Publisher · View at Google Scholar · View at Scopus
  9. D. M. Cox, D. J. Trevor, R. L. Whetten, and A. Kaldor, “Aluminum clusters: ionization thresholds and reactivity toward deuterium, water, oxygen, methanol, methane, and carbon monoxide,” Journal of Physical Chemistry, vol. 92, no. 2, pp. 421–429, 1988. View at Google Scholar · View at Scopus
  10. V. Polshettiwar and R. S. Varma, “Green chemistry by nano-catalysis,” Green Chemistry, vol. 12, no. 5, pp. 743–754, 2010. View at Publisher · View at Google Scholar · View at Scopus
  11. V. Polshettiwar, B. Baruwati, and R. S. Varma, “Self-assembly of metal oxides into three-dimensional nanostructures: synthesis and application in catalysis,” ACS Nano, vol. 3, no. 3, pp. 728–736, 2009. View at Publisher · View at Google Scholar · View at Scopus
  12. V. Polshettiwar, M. N. Nadagouda, and R. S. Varma, “The synthesis and applications of a micro-pine-structured nanocatalyst,” Chemical Communications, no. 47, pp. 6318–6320, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. A. Fihri, R. Sougrat, R. B. Rakhi et al., “Nanoroses of nickel oxides: synthesis, electron tomography study, and application in CO oxidation and energy storage,” ChemSusChem, vol. 5, no. 7, pp. 1241–1248, 2012. View at Publisher · View at Google Scholar
  14. K. Shimizu, R. Sato, and A. Satsuma, “Direct C–C cross-coupling of secondary and primary alcohols catalyzed by a γ-alumina-supported silver subnanocluster,” Angewandte Chemie—International Edition, vol. 48, no. 22, pp. 3982–3986, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. A. Murugadoss, P. Goswami, A. Paul, and A. Chattopadhyay, “‘Green’ chitosan bound silver nanoparticles for selective C–C bond formation via in situ iodination of phenols,” Journal of Molecular Catalysis A, vol. 304, no. 1-2, pp. 153–158, 2009. View at Publisher · View at Google Scholar · View at Scopus
  16. C. A. Witham, W. Huang, C. Tsung, J. N. Kuhn, G. A. Somorjai, and F. D. Toste, “Converting homogeneous to heterogeneous in electrophilic catalysis using monodisperse metal nanoparticles,” Nature Chemistry, vol. 2, no. 1, pp. 36–41, 2010. View at Publisher · View at Google Scholar · View at Scopus
  17. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford Publication, New York, NY, USA, 1998.
  18. M. A. P. Martins, C. P. Frizzo, D. N. Moreira, L. Buriol, and P. Machado, “Solvent-free heterocyclic synthesis,” Chemical Reviews, vol. 109, no. 9, pp. 4140–4182, 2009. View at Publisher · View at Google Scholar · View at Scopus
  19. P. J. Walsh, H. Li, and C. A. de Parrodi, “A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions,” Chemical Reviews, vol. 107, no. 6, pp. 2503–2545, 2007. View at Publisher · View at Google Scholar · View at Scopus
  20. K. Tanaka and F. Toda, “Solvent-free organic synthesis,” Chemical Reviews, vol. 100, no. 3, pp. 1025–1074, 2000. View at Google Scholar · View at Scopus
  21. G. Nagendrappa, “Organic synthesis under solvent-free condition: an environmentally benign procedure—II,” Resonance, vol. 7, no. 10, pp. 59–68, 2002. View at Google Scholar
  22. K. Tanaka, Solvent-Free Organic Synthesis, Wiley-VCH, Weinheim, Germany, 2009.
  23. M. Fathalla, C. M. Lawrence, N. Zhang, J. L. Sessler, and J. Jayawickramarajah, “Base-pairing mediated non-covalent polymers,” Chemical Society Reviews, vol. 38, no. 6, pp. 1608–1620, 2009. View at Publisher · View at Google Scholar · View at Scopus
  24. S. Sivakova and S. J. Rowan, “Nucleobases as supramolecular motifs,” Chemical Society Reviews, vol. 34, no. 1, pp. 9–21, 2005. View at Publisher · View at Google Scholar · View at Scopus
  25. M. W. Powner, B. Gerland, and J. D. Sutherland, “Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions,” Nature, vol. 459, no. 7244, pp. 239–242, 2009. View at Publisher · View at Google Scholar · View at Scopus
  26. O. S. Pedersen and E. B. Pedersen, “Non-nucleoside reverse transcriptase inhibitors: the NNRTI boom,” Antiviral Chemistry and Chemotherapy, vol. 10, no. 6, pp. 285–314, 1999. View at Google Scholar · View at Scopus
  27. A. R. Dinner, G. M. Blackburn, and M. Karplus, “Uracil-DNA glycosylase acts by substrate autocatalysis,” Nature, vol. 413, no. 6857, pp. 752–755, 2001. View at Publisher · View at Google Scholar · View at Scopus
  28. F. C. Tucci, Y. F. Zhu, Z. Guo et al., “3-(2-aminoalkyl)-1-(2,6-difluorobenzyl)-5-(2-fluoro-3-methoxyphenyl)-6-methyluracils as orally bioavailable antagonists of the human gonadotropin releasing hormone receptor,” Journal of Medicinal Chemistry, vol. 47, no. 14, pp. 3483–3486, 2004. View at Publisher · View at Google Scholar · View at Scopus
  29. D. P. Sutherlin, D. Sampath, M. Berry et al., “Discovery of (thienopyrimidin-2-yl)aminopyrimidines as potent, selective, and orally available Pan-PI3-kinase and dual Pan-PI3-kinase/mTOR inhibitors for the treatment of cancer,” Journal of Medicinal Chemistry, vol. 53, no. 3, pp. 1086–1097, 2010. View at Publisher · View at Google Scholar · View at Scopus
  30. S. Manta, E. Tsoukala, N. Tzioumaki, C. Kiritsis, J. Balzarini, and D. Komiotis, “Synthesis of 4,6-dideoxy-3-fluoro-2-keto-β-d-glucopyranosyl analogues of 5-fluorouracil, N6-benzoyl adenine, uracil, thymine, N4-benzoyl cytosine and evaluation of their antitumor activities,” Bioorganic Chemistry, vol. 38, no. 2, pp. 48–55, 2010. View at Publisher · View at Google Scholar · View at Scopus
  31. T. Lundqvist, S. L. Fisher, G. Kern et al., “Exploitation of structural and regulatory diversity in glutamate racemases,” Nature, vol. 447, no. 7146, pp. 817–822, 2007. View at Publisher · View at Google Scholar · View at Scopus
  32. J. B. Parker, M. A. Bianchet, D. J. Krosky, J. I. Friedman, L. M. Amzel, and J. T. Stivers, “Enzymatic capture of an extrahelical thymine in the search for uracil in DNA,” Nature, vol. 449, no. 7161, pp. 433–437, 2007. View at Publisher · View at Google Scholar · View at Scopus
  33. A. Okamoto, “Chemical approach toward efficient DNA methylation analysis,” Organic and Biomolecular Chemistry, vol. 7, no. 1, pp. 21–26, 2009. View at Publisher · View at Google Scholar · View at Scopus
  34. A. Samanta, D. D. Leonidas, S. Dasgupta, T. Pathak, S. E. Zographos, and N. G. Oikonomakos, “Morpholino, piperidino, and pyrrolidino derivatives of pyrimidine nucleosides as inhibitors of ribonuclease A: synthesis, biochemical, and crystallographic evaluation,” Journal of Medicinal Chemistry, vol. 52, no. 4, pp. 932–942, 2009. View at Publisher · View at Google Scholar · View at Scopus
  35. R. Rico-Gómez, J. M. López-Romero, J. Hierrezuelo, J. Brea, M. I. Loza, and M. Pérez-González, “Synthesis of new mannosyl, galactosyl and glucosyl theophylline nucleosides with potential activity as antagonists of adenosine receptors. DEMA-induced cyclization of glycosylideneiminouracils,” Carbohydrate Research, vol. 343, no. 5, pp. 855–864, 2008. View at Publisher · View at Google Scholar · View at Scopus
  36. S. Das and A. J. Thakur, “A clean, highly efficient and one-pot green synthesis of aryl/alkyl/heteroaryl-substituted bis(6-amino-1,3-dimethyluracil-5-yl)methanes in water,” European Journal of Organic Chemistry, no. 12, pp. 2301–2308, 2011. View at Publisher · View at Google Scholar · View at Scopus
  37. J. W. Blunt, B. R. Copp, W. P. Hu, M. H. G. Munro, P. T. Northcotec, and M. R. Prinsepd, “Marine natural products,” Natural Product Reports, vol. 26, no. 1, pp. 170–224, 2008. View at Google Scholar
  38. V. E. Semenov, V. D. Akamsin, V. S. Reznik et al., “New type of pyrimidinophanes with α,ω-bis(uracil-1-yl)alkane and bis(uracil-5-yl)methane units,” Mendeleev Communications, vol. 11, no. 3, pp. 96–97, 2001. View at Google Scholar · View at Scopus
  39. V. K. Das, R. R. Devi, P. K. Raul, and A. J. Thakur, “Nano rod-shaped and reusable basic Al2O3 catalyst for N-formylation of amines under solvent-free conditions: a novel, practical and convenient 'NOSE' approach,” Green Chemistry, vol. 14, no. 3, pp. 847–854, 2012. View at Publisher · View at Google Scholar · View at Scopus
  40. V. K. Das, R. R. Devi, and A. J. Thakur, “Recyclable, highly efficient and low cost nano-MgO for amide synthesis under SFRC: a convenient and greener “NOSE” approach,” Applied Catalysis A, vol. 456, pp. 118–125, 2013. View at Publisher · View at Google Scholar
  41. V. K. Das, M. Borah, and A. J. Thakur, “Piper-betle-shaped nano-S-catalyzed synthesis of 1-amidoalkyl-2-naphthols under solvent-free reaction condition: a greener nanoparticle-catalyzed organic synthesis enhancement approach,” Journal of Organic Chemistry, vol. 78, no. 7, pp. 3361–3366, 2013. View at Publisher · View at Google Scholar
  42. M. Shojaie-Bahaabad and E. Taheri-Nassaj, “Economical synthesis of nano alumina powder using an aqueous sol-gel method,” Materials Letters, vol. 62, no. 19, pp. 3364–3366, 2008. View at Publisher · View at Google Scholar · View at Scopus
  43. C. Huang, J. Wang, and C. Huang, “Sintering behavior and microwave dielectric properties of nano alpha-alumina,” Materials Letters, vol. 59, no. 28, pp. 3746–3749, 2005. View at Publisher · View at Google Scholar · View at Scopus
  44. Y. Zhang, J. Liu, R. He, Q. Zhang, X. Zhang, and J. Zhu, “Synthesis of alumina nanotubes using carbon nanotubes as templates,” Chemical Physics Letters, vol. 360, no. 5-6, pp. 579–584, 2002. View at Publisher · View at Google Scholar · View at Scopus