A convenient method for the preparation of 2-aminobenzophenone derivaties under ultrasonic irradiation

A convenient method for the preparation of 2-aminobenzophenone derivaties under ultrasonic irradiation

A quick and convenient method for the preparation of 2-aminobenzophenone derivatives is described.This approach consists of the nucleophilic substitution reaction of nitrobenzenes by phenylacetonitrile under conventional and ultrasonic conditions followed by reduction of the produced 2,1-benzisoxazole to 2-aminobenzophenone. This 2-step reaction was studied by changing the reaction parameters (reaction temperature, ultrasound power, and reaction time). The results clearly demonstrated that using ultrasound irradiation results in a high yield within a short reaction time.

___

  • 1. D.A. Walsh, Synthesis, 677-88 (1980).
  • 2. J.C.E. Simpson, CM. Atkinson, K. Schofield and O. Stephenson, J. Chem. Soc. 646-57 (1945).
  • 3. A. Walser and G. Silverman, J. Heterocycl. Chem. 10, 883-4 (1973).
  • 4. Y. Nakamura and T. Ukita, Org. Lett. 4, 2317-20 (2002).
  • 5. A.I. Rachlin, U. S. Patent 3261870 (1962).
  • 6. G. Gamboni, W. Schmid and A. Sutter, U.S. Patent 4236006, (1980).
  • 7. E.A. Fehnel, J. Org. Chem. 31, 2899-2902 (1966).
  • 8. H. Matsumoto and T. Horiuchi, U.S. Patent 6310249 Bl (2001).
  • 9. A. Capelli, G.P. Mohr, A. Gallelli, M. Rizzo, M. Anzini, S. Vomero, L. Mennumi, F. Ferrari, F. Makovec, M.C.Menziani, P.G.D. Benedetti and G. Giorgi, J. Med. Chem. 47, 2574-86 (2004).
  • 10. P. Hewawasam, W. Fan, M. Ding, K. Flint, D. Cook, G.D. Goggins, R.A. Myers, V.K. Gribkoff, C.G. Bassard, S.I. Dworetzky, J.E. Starrett and N.J. Lodge, J. Med. Chem. 46, 2819-22 (2003).
  • 11. H. Ma, A.K.Y. Jen, J. Wu, X. Wu and S. Liu, Chem. Matter. 11, 2218-25 (1999).
  • 12. J.L. Kim, J.K. Kim, H.N. Cho, D.Y. Kim, C.Y. Kim and S.I. Hong, Macromolecules, 33, 5880-85 (2000).
  • 13. X.L. Chen and S.A. Jenekhe, Macromolecules, 33, 4610-12 (2000).
  • 14. Liangde Lu and S.A. Jenekhe, Macromolecules, 34, 6249-54 (2001).
  • 15. T.W. Kwon, M.M. Alam and S.A. Jenekhe, Chem. Matter. 16, 4657-66 (2004).
  • 16. L.H. Sternbach, Angew. Chem. Internat. Edit. 10, 34-43 (1971).
  • 17. G. Semple, H. Ryder, D.P. Rooker, A.R. Batt, D.A. Kendrick, M. Szelke, M. Ohta, M. Satoh, A. Nishiha, S. Akuzawa and K. Miyata, J. Med. Chem. 40, 331-41 (1997).
  • 18. F. Mauri and S.P.A. Ravizza, U.S. Patent 4511510 (1985).
  • 19. N. Micale, R. Vairagoundar, A.G. Yakovlev and A.P. Kozikowski, J. Med. Chem. 47, 6455-58 (2004).
  • 20. M.H. Bolli, J. Marfurt, C. Grisostomi, C. Boss, C. Binkert, P. Hess, A. Treiber, E. Thorin, K. Morrison, S.Buchmann, D. Bur, H. Ramuz, M. Clozel, W. Fischli and T. Weller, J. Med. Chem. 47, 2776-95 (2004).
  • 21. I.M. Buck, J.W. Black, T. Cooke, D.J. Dunstone, J.D. Gaffen, E.A. Harper, R.A.D. Hull, S.B. Kalindjian, E.J.Lilley, I.D. Linney, C.M.R. Low, K.I.M. Steel, D.A. Sykes, M.J. Tozer and G.F. Watt, J. Med. Chem. 48,6803-12 (2005).
  • 22. R.V. Coombs, R.P. Danna, M. Denzer, G.E. Hardtmann, B. Huegi, G. Koletar, J. Koletar, H. Ott and E.Jukniewicz, J. Med. Chem. 16, 1237-45 (1973).
  • 23. W.J. Welstead, J.H.W. Moran, H.F. Stauffer, L.B. Turnbull and L.F. Sancilio, J. Med. Chem. 22, 1074-79 (1979).
  • 24. J.P. Liou, C.W. Chang, J.S. Song, Y.N. Yang, C.F. Yeh, H.Y. Tseng, Y.K. Lo, Y.L. Chang, CM. Chang and H.P. Hsieh, J. Med. Chem. 45, 2556-62 (2002).
  • 25. J.P. Liou, J.Y. Chang, C.W. Chang, C.Y. Chang, N. Mahindroo and H.P. Hsieh, J. Med. Chem. 47, 2897-2905 (2004).
  • 26. J.P- Liou, Y.L. Chang, F.M. Kuo, C.W. Chang, H.Y. Tseng, C.C. Wang, Y.N. Yang, J.Y. Chang, S.J. Lee and H.P. Hsieh, J. Med. Chem. 47, 4247-57 (2004).
  • 27. H.J. Scheifele and D.F. Detarr, Org. Synth. Coll. 4, 34-8 (1963).
  • 28. L.H. Sternbach, R.I. Fryer, W. Metlesics, G. Sach and A. Stempel, J. Org. Chem. 27, 3781-88 (1962).
  • 29. J.C.E. Simpson and O. Stephenson, J. Chem. Soc. 353-58 (1942).
  • 30. J.N. Walker, J. Org. Chem. 27, 1929-30 (1962).
  • 31. K.H. Wunsch and A.J. Boulton, Adv. Heterocycl. Chem. 8, 303-20 (1969).
  • 32. F. Faltsi and F. Kloiber, Monatsh. Chem. 53/54, 620-37 (1929).
  • 33. G. Heller, J. Prakt. Chem. 77, 145-71 (1908).
  • 34. R. Scholl, Monatsh. Chem. 34, 1011 (1913).
  • 35. R.B. Davis and L.C. Pizzini, J. Org. Chem. 25, 1884-88 (1960).
  • 36. M. Mamo, S. Nicoletti and C. Tat, Molecules, 7, 618-27 (2002).
  • 37. M.A. Margulis, High Energ. Chem. 38, 135-42 (2004).
  • 38. T.J. Mason, Chem. Soc. Rev. 6, 443-51 (1997).
  • 39. J.L. Luche, "Synthetic Organic Sonochemistry", Chapter 2, pp. 55-56, Plenum Press, New York (1999).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

A convenient method for the preparation of 2-aminobenzophenone derivaties under ultrasonic irradiation

Javad SAFAEI-GHOMI, Manouchehr FADAEIAN, Alireza HATAMI

Synthesis and Characterization of Oligo-2-[(2-hydroxymethylphenylimino) methyl] phenol and Oligo-2-[(2-hydroxymethylphenylimino) methyl]-5-bromo-phenol

İsmet KAYA, Ayşe Erçağ And Süleyman ÇULHAOĞLU

A Convenient Method for the Preparation of 2-Aminobenzophenone Derivatives under Ultrasonic Irradiation

Javad SAFAEI-GHOMI, Manouchehr FADAEIAN, Alireza HATAMI

Studies on the Preparation of a,w -Telechelic Polymers by the Combination of Reverse Atom Transfer Radical Polymerization and Atom Transfer Radical Coupling Processes

Binnur AYDOĞAN, Yusuf YAĞCI

New Aromatic Polyamide with Azo and Phosphine Oxide Groups in the Main Chain

Khalil FAGHIHI, Mohsen HAGIBEYGI

Plasma-Initiated Polymerization of (2-Methacryloyloxyethyl) Thrimethyl Ammonium Chloride

Yangang HE, Gang LI, Jing MIAO, Xueqing YU, Fang YANG

Preparation and Characterization of an Atenolol Selective Electrode Based on a PVC Matrix Membrane

Nabil S. NASSORY, Shahbaz A. Maki And Mutaz A. ALI, Mutaz A. ALI

Electron affinities, solvation energies and redox potentials of some chalcones: Substituents' effect and correlation with semi-empirical MO energies

Abdur RAHMAN, Rumana QRESHI, Mehvish KIRAN, Farzana Latif ANSARI

Synthesis and Spectral Characterisation of Chloro Organotin(IV) di[3(2`-hydroxyphenyl)-5-(4-substituted phenyl) Pyrazolinates]

Umesh Nath TRIPATHI, Mohammad Safi AHMAD, Goriparthi VENUBABU

Gold(III) Complex of Caffeine: Synthesis, Isolation and Spectroscopic Characterization

Bojidarka IVANOVA