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Journal of Chemistry
Volume 2013 (2013), Article ID 364036, 9 pages
http://dx.doi.org/10.1155/2013/364036
Research Article

Comparative Studies on Conventional and Ultrasound-Assisted Synthesis of Novel Homoallylic Alcohol Derivatives Linked to Sulfonyl Dibenzene Moiety in Aqueous Media

1Department of Mathematics and Natural Sciences, Faculty of Science and Technology, University of Stavanger, 4036 Stavanger, Norway
2Department of Green Chemistry, National Research Centre, Dokki, Cairo 12622, Egypt
3Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koam, Menoufia 32515, Egypt

Received 17 January 2012; Revised 23 May 2012; Accepted 31 May 2012

Academic Editor: Barbara Zajc

Copyright © 2013 Mohamed F. Mady 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. G. Cravotto and P. Cintas, “Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications,” Chemical Society Reviews, vol. 35, no. 2, pp. 180–196, 2006. View at Publisher · View at Google Scholar
  2. K. Bang, K. Lee, Y. K. Park, and P. H. Lee, “Sonochemical Reformatsky reaction using indium,” Bulletin of the Korean Chemical Society, vol. 23, no. 9, pp. 1272–1276, 2002. View at Google Scholar · View at Scopus
  3. P. H. Lee, “Indium and gallium-mediated addition reactions,” Bulletin of the Korean Chemical Society, vol. 28, no. 1, pp. 17–28, 2007. View at Publisher · View at Google Scholar
  4. T. S. Saleh and N. M. Abd EL-Rahman, “Ultrasound promoted synthesis of substituted pyrazoles and isoxazoles containing sulphone moiety,” Ultrasonics Sonochemistry, vol. 16, no. 2, pp. 237–242, 2009. View at Publisher · View at Google Scholar · View at Scopus
  5. M. Mokhtar, T. S. Saleh, N. S. Ahmed, S. A. Al-Thabaiti, and R. A. Al-Shareef, “An eco-friendly N-sulfonylation of amines using stable and reusable Zn-Al-hydrotalcite solid base catalyst under ultrasound irradiation,” Ultrasonics Sonochemistry, vol. 18, no. 1, pp. 172–176, 2011. View at Publisher · View at Google Scholar · View at Scopus
  6. Y. J. Bian, J. T. Li, and T. S. Li, “Applications of ultrasound in organic synthesis using metal reagent,” Chinese Journal of Organic Chemistry, vol. 22, p. 227, 2002. View at Google Scholar
  7. J. Yoo, K. E. Oh, G. Keum, S. B. Kang, and Y. Kim, “Indium-mediated monoallylation of carbonyl compounds with allylic chlorides and bisallylation of 2-pyridyl carboxylates with allylic halides in aqueous media,” Polyhedron, vol. 19, no. 5, pp. 549–551, 2000. View at Publisher · View at Google Scholar · View at Scopus
  8. S. Y. Park, H. J. Han, B. Yoo et al., “Facile synthesis of β-ketoesters by indium-mediated reaction of acyl cyanides with ethyl bromoacetate under ultrasonication,” Bulletin of the Korean Chemical Society, vol. 26, no. 6, pp. 878–879, 2005. View at Google Scholar · View at Scopus
  9. G. R. Soengas, “Studies on indium-mediated additions to lactones: synthesis of 2-deoxy-2-substituted-3-ulosonic acids,” Tetrahedron: Asymmetry, vol. 21, no. 18, pp. 2249–2253, 2010. View at Publisher · View at Google Scholar
  10. J. Lindley, J. P. Lorimer, and T. J. Mason, “Enhancement of an Ullmann coupling reaction induced by ultrasound,” Ultrasonics, vol. 24, no. 5, pp. 292–293, 1986. View at Google Scholar · View at Scopus
  11. T. Otzen, E. G. Wempe, B. Kunz et al., “Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans—synthesis and biological activity of new 2,4-diaminopyrimidines and 4-substituted 4-aminodiphenyl sulfones,” Journal of Medicinal Chemistry, vol. 47, no. 1, pp. 240–253, 2004. View at Publisher · View at Google Scholar · View at Scopus
  12. Z. Y. Sun, E. Botros, A. D. Su et al., “Sulfoxide-containing aromatic nitrogen mustards as hypoxia-directed bioreductive cytotoxins,” Journal of Medicinal Chemistry, vol. 43, no. 22, pp. 4160–4168, 2000. View at Publisher · View at Google Scholar · View at Scopus
  13. I. W. Davies, J. F. Marcoux, E. G. Corley et al., “A practical synthesis of a COX-2-specific inhibitor,” Journal of Organic Chemistry, vol. 65, no. 25, pp. 8415–8420, 2000. View at Publisher · View at Google Scholar · View at Scopus
  14. J. B. McMahon, R. J. Gulakowski, O. S. Weislow et al., “Diarylsulfones, a new chemical class of nonnucleoside antiviral inhibitors of human immunodeficiency virus type 1 reverse transcriptase,” Antimicrobial Agents and Chemotherapy, vol. 37, no. 4, pp. 754–760, 1993. View at Google Scholar · View at Scopus
  15. N. Neamati, A. Mazumder, H. Zhao et al., “Diarylsulfones, a novel class of human immunodeficiency virus type 1 integrase inhibitors,” Antimicrobial Agents and Chemotherapy, vol. 41, no. 2, pp. 385–393, 1997. View at Google Scholar · View at Scopus
  16. G. A. Doherty, T. Kamenecka, E. McCauley et al., “N-aryl 2,6-dimethoxybiphenylalanine analogues as VLA-4 antagonists,” Bioorganic and Medicinal Chemistry Letters, vol. 12, no. 5, pp. 729–731, 2002. View at Publisher · View at Google Scholar · View at Scopus
  17. A. M. Faucher, P. W. White, C. Brochu, C. Grand-Maître, J. Rancourt, and G. Fazal, “Discovery of small-molecule inhibitors of the ATPase activity of human papillomavirus E1 helicase,” Journal of Medicinal Chemistry, vol. 47, no. 1, pp. 18–21, 2004. View at Publisher · View at Google Scholar · View at Scopus
  18. M. Tomida, Y. Yamamoto-Yamaguchi, and M. Hozumi, “Pregnancy associated increase in mRNA for soluble D-factor/LIF receptor in mouse liver,” FEBS Letters, vol. 334, no. 2, pp. 193–197, 1993. View at Publisher · View at Google Scholar · View at Scopus
  19. S. E. Denmark and J. Fu, “Catalytic enantioselective allylation with chiral Lewis bases,” Chemical Communications, no. 2, pp. 167–170, 2003. View at Publisher · View at Google Scholar
  20. C. Petrier and J. L. Luche, “Allylzinc reagents additions in aqueous media,” The Journal of Organic Chemistry, vol. 50, no. 6, pp. 910–912, 1985. View at Publisher · View at Google Scholar
  21. Z. Zha, Y. Wang, G. Yang, L. Zhang, and Z. Wang, “Efficient barbier reaction of carbonyl compounds improved by a phase transfer catalyst in water,” Green Chemistry, vol. 4, no. 6, pp. 578–580, 2002. View at Publisher · View at Google Scholar · View at Scopus
  22. M. K. Basu and B. K. Banik, “Samarium-mediated Barbier reaction of carbonyl compounds,” Tetrahedron Letters, vol. 42, no. 2, pp. 187–189, 2001. View at Publisher · View at Google Scholar · View at Scopus
  23. Z. Wang, S. Yuan, and C. J. Li, “Gallium-mediated allylation of carbonyl compounds in water,” Tetrahedron Letters, vol. 43, no. 29, pp. 5097–5099, 2002. View at Publisher · View at Google Scholar · View at Scopus
  24. C. J. Li and T. H. Chan, “Organometallic reactions in aqueous media with indium,” Tetrahedron Letters, vol. 32, no. 48, pp. 7017–7020, 1991. View at Publisher · View at Google Scholar · View at Scopus
  25. B. Xu and G. B. Hammond, “On the nature of organoindium intermediates: the formation of readily isolable difluoropropargylindium reagents and their regioselectivity towards electrophilic substitutions,” Chemistry, vol. 14, no. 32, pp. 10029–10035, 2008. View at Publisher · View at Google Scholar
  26. R. Kargbo, Y. Takahashi, S. Bhor, G. R. Cook, G. C. Lloyd-Jones, and I. R. Shepperson, “Readily accessible, modular, and tuneable BINOL 3,3- perfluoroalkylsulfones: highly efficient catalysts for enantioselective in-mediated imine allylation,” Journal of the American Chemical Society, vol. 129, no. 13, pp. 3846–3847, 2007. View at Publisher · View at Google Scholar · View at Scopus
  27. K. L. Tan and E. N. Jacobsen, “Indium-mediated asymmetric allylation of acylhydrazones using a chiral urea catalyst,” Angewandte Chemie, vol. 119, no. 8, pp. 1337–1339, 2007. View at Publisher · View at Google Scholar
  28. T. D. Haddad, L. C. Hirayama, and B. Singaram, “Indium-mediated asymmetric barbier-type allylations: additions to aldehydes and ketones and mechanistic investigation of the organoindium reagents,” The Journal of Organic Chemistry, vol. 75, no. 3, pp. 642–649, 2010. View at Publisher · View at Google Scholar
  29. P. Cintas, G. Palmisano, and G. Cravotto, “Power ultrasound in metal-assisted synthesis: from classical Barbier-like reactions to click chemistry,” Ultrasonics Sonochemistry, vol. 18, no. 4, pp. 836–841, 2011. View at Publisher · View at Google Scholar · View at Scopus
  30. B. Alcaide, P. Almendros, and T. M. del Campo, “Highly stereoselective metal-mediated entry to functionalized tetrahydrothiophenes by barbier-type carbonyl-addition reactions,” European Journal of Organic Chemistry, vol. 2008, no. 15, pp. 2628–2634, 2008. View at Publisher · View at Google Scholar
  31. R. B. Kargbo and G. R. Cook, “Stereoselective indium-mediated allylation reactions,” Current Organic Chemistry, vol. 11, no. 15, pp. 1287–1309, 2007. View at Publisher · View at Google Scholar
  32. J. S. Yadav, B. V. Subba Reddy, P. Vishnumurthy, and S. K. Biswas, “Indium-mediated allylation/propargylation of α-diazoketones: a facile synthesis of 1-bromo-2-alkyl- or 2-arylpent-4-en-2-ols,” Tetrahedron Letters, vol. 48, no. 38, pp. 6641–6643, 2007. View at Publisher · View at Google Scholar · View at Scopus
  33. T. P. Loh and G. L. Chau, “Discovery of indium complexes as water-tolerant Lewis acids,” Chemical Communications, vol. 26, pp. 2739–2749, 2006. View at Publisher · View at Google Scholar
  34. Y. Yamamoto and N. Asao, “Selective reactions using allylic metals,” Chemical Reviews, vol. 93, no. 6, pp. 2207–2293, 1993. View at Google Scholar · View at Scopus
  35. W. H. Reinhard, “Diastereogenic addition of crotylmetal compounds to aldehydes,” Angewandte Chemie, vol. 21, no. 8, pp. 555–566, 1982. View at Publisher · View at Google Scholar
  36. Y. Yoshinori, “Acyclic stereocontrol via allylic organometallic compounds,” Accounts of Chemical Research, vol. 20, no. 7, pp. 243–249, 1987. View at Publisher · View at Google Scholar
  37. A. N. Pae and Y. S. Cho, “Indium-mediated organic reactions in aqueous media,” Current Organic Chemistry, vol. 6, no. 8, pp. 715–737, 2002. View at Publisher · View at Google Scholar
  38. J. Podlech and T. C. Maier, “Indium in organic synthesis,” Synthesis, no. 5, pp. 633–655, 2003. View at Google Scholar · View at Scopus
  39. C. J. Li and T. H. Chan, “Organic syntheses using indium-mediated and catalyzed reactions in aqueous media,” Tetrahedron, vol. 55, no. 37, pp. 11149–11176, 1999. View at Publisher · View at Google Scholar · View at Scopus
  40. J. Augé, N. Lubin-Germain, and J. Uziel, “Recent advances in indium-promoted organic reactions,” Synthesis, no. 12, pp. 1739–1764, 2007. View at Publisher · View at Google Scholar · View at Scopus
  41. A. W. Erian, S. M. Sherif, and H. M. Gaber, “The chemistry of α-haloketones and their utility in heterocyclic synthesis,” Molecules, vol. 8, no. 11, pp. 793–865, 2003. View at Google Scholar · View at Scopus
  42. H. Xian and J. Pi, “A novel synthesis of sulfones via the 0.0-diethylphosphorotellurite ion-assisted coupling of arenesulfonyl chlorides with active halides,” Synthetic Communications, vol. 20, no. 15, pp. 2291–2295, 1990. View at Publisher · View at Google Scholar
  43. C. L. Xu and Z. C. Chen, “Reaction of isopropylidene 5-tosyloxymalonate with alkyl halides- a new sulfur-oxygen scission of tosylate,” Tetrahedron Letters, vol. 32, no. 25, pp. 2933–2934, 1991. View at Publisher · View at Google Scholar · View at Scopus
  44. P. Sunitha, S. Kumar, B. R. Rao, and G. Venkateshwarlu, “Microwave assisted efficient synthesis of β-keto-sulfones in aqueous medium,” Green Chemistry Letters and Reviews, vol. 1, no. 3, pp. 179–183, 2008. View at Publisher · View at Google Scholar
  45. G. Evano, N. Blanchard, and M. Toumi, “Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis,” Chemical Reviews, vol. 108, no. 8, pp. 3054–3131, 2008. View at Publisher · View at Google Scholar · View at Scopus
  46. I. P. Beletskaya and A. V. Cheprakov, “Copper in cross-coupling reactions: the post-Ullmann chemistry,” Coordination Chemistry Reviews, vol. 248, no. 21–24, pp. 2337–2364, 2004. View at Publisher · View at Google Scholar
  47. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, and M. Lemaire, “Aryl−Aryl bond formation one century after the discovery of the Ullmann reaction,” Chemical Reviews, vol. 102, no. 5, pp. 1359–1470, 2002. View at Publisher · View at Google Scholar
  48. J. Zou, F. Li, and G. F. Tao, “Microwave-assisted synthesis of diaryl or aryl-alkyl sulfones without catalyst,” Chinese Chemical Letters, vol. 20, no. 1, pp. 17–20, 2009. View at Publisher · View at Google Scholar
  49. M. B. Isaac and C. Tak-Hang, “Indium mediated coupling of aldehydes with allyl bromides in aqueous media. The issue of regio- and diastereo-selectivity,” Tetrahedron Letters, vol. 36, no. 49, pp. 8957–8960, 1995. View at Publisher · View at Google Scholar · View at Scopus
  50. X. H. Tan, Y. Q. Hou, C. Huang, L. Liu, and Q. X. Guo, “SnCl2-mediated carbonyl allylation in fully aqueous media,” Tetrahedron, vol. 60, no. 29, pp. 6129–6136, 2004. View at Publisher · View at Google Scholar · View at Scopus
  51. R. Sjoholm, R. Rairama, and M. Ahonen, “Zinc mediated allylation of aldehydes and ketones with cinnamyl chloride in aqueous medium,” Journal of the Chemical Society, Chemical Communications, no. 10, pp. 1217–1218, 1994. View at Publisher · View at Google Scholar
  52. R. Keltjens, S. K. Vadivel, R. De Gelder, A. J. H. Klunder, and B. Zwanenburg, “Diastereoselective zinc-mediated Barbier-type allylation and propargylation of 3-formylcephalosporins,” European Journal of Organic Chemistry, no. 9, pp. 1749–1758, 2003. View at Google Scholar · View at Scopus
  53. L. A. Paquette, “Fundamental mechanistic characteristics and synthetic applications of allylations promoted by indium metal in aqueous media,” Synthesis, no. 5, pp. 765–774, 2003. View at Google Scholar · View at Scopus
  54. H. E. Zimmerman and M. D. Traxler, “The stereochemistry of the Ivanov and Reformatsky reactions. I,” Journal of the American Chemical Society, vol. 79, no. 8, pp. 1920–1923, 1957. View at Google Scholar · View at Scopus
  55. N. M. Abd EL-Rahman, T. S. Saleh, and M. F. Mady, “Ultrasound assisted synthesis of some new 1,3,4-thiadiazole and bi(1,3,4-thiadiazole) derivatives incorporating pyrazolone moiety,” Ultrasonics Sonochemistry, vol. 16, no. 1, pp. 70–74, 2009. View at Publisher · View at Google Scholar · View at Scopus
  56. G. A. Hill and E. L. Kropa, “Some halogenated pinacolones,” Journal of the American Chemical Society, vol. 55, no. 6, pp. 2509–2512, 1933. View at Google Scholar · View at Scopus
  57. S. V. Ley and A. W. Thomas, “Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation,” Angewandte Chemie, vol. 42, no. 44, pp. 5400–5449, 2003. View at Publisher · View at Google Scholar
  58. E. J. Yoo, M. Ahlquist, S. H. Kim et al., “Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: Controlling selectivity,” Angewandte Chemie, vol. 46, no. 10, pp. 1730–1733, 2007. View at Publisher · View at Google Scholar · View at Scopus
  59. E. J. Yoo and S. Chang, “A new route to indolines by the Cu-catalyzed cyclization reaction of 2-ethynylanilines with sulfonyl azides,” Organic Letters, vol. 10, no. 6, pp. 1163–1166, 2008. View at Publisher · View at Google Scholar
  60. T. Yasukawa, H. Miyamura, and S. Kobayashi, “Copper-catalyzed, aerobic oxidative cross-coupling of alkynes with arylboronic acids: remarkable selectivity in 2,6-lutidine media,” Organic & Biomolecular Chemistry, vol. 9, pp. 6208–6210, 2011. View at Publisher · View at Google Scholar
  61. Y. Kegelaers, O. Eulaerts, J. Reisse, and N. Segebarth, “On the quantitative measure of a sonochemical effect in heterogeneous sonochemistry,” European Journal of Organic Chemistry, no. 19, pp. 3683–3688, 2001. View at Google Scholar · View at Scopus
  62. V. K. Patel, D. J. Sen, H. U. Patel, and C. N. Patel, “Sonochemistry: The effect of sonic waves on chemical systems,” Journal of Chemical and Pharmaceutical Research, vol. 2, p. 573, 2010. View at Google Scholar