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Chemistry of Heterocyclic Compounds

, Volume 43, Issue 10, pp 1336–1341 | Cite as

Syntheses of substituted 8-(aminobenzyl)dinaphthodioxaphosphocine 8-oxides

  • M. F. Stephen Babu
  • B. Hari Babu
  • K. R. Kishore Kumar Reddy
  • C. Naga Raju
  • C. Suresh Reddy
Article

Abstract

Substituted (8-aminobenzyl)dinaphthodioxaphosphocine 8-oxides were prepared in a two-step process. The first step of the reaction is one-pot synthesis of α-aminophosphonates by the reaction of aldehydes, amines, and trialkyl phosphite in the presence of ceric ammonium nitrate. The second step is cyclization of α-aminophosphonates with bis(2-hydroxy-1-naphthyl)methane in the presence of a catalytic amount of p toluenesulphonic acid under reflux conditions. Their structures were established by elemental analyses, IR, 1H, 13C, 31P NMR, and mass spectral data.

Keywords

α-aminophosphonates bis(2-hydroxy-1-naphthyl)methane dinaphthodioxaphosphocine 8-oxides 

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References

  1. 1.
    P. Kafarki, B. Lejezak, Phosphorus, Sulfur, Silicon, 63, 193 (1991).CrossRefGoogle Scholar
  2. 2.
    R. Hirschmann, A. B. Simith, C. M. Taylor, P. A. Benkovie, S. D. Taylor, K. M. Yager, P. A. Sprengler, S. J. Benkovie, Science, 234, 2765 (1994).Google Scholar
  3. 3.
    S. K. Chung, D. O. Kang, Tetrahedron: Asymmetry, 7, 21 (1996).CrossRefGoogle Scholar
  4. 4.
    B. Stowasser, K. H. Budt, L. Jian-Qi, A. Peyman, D. Ruppert, Tetrahedron Lett., 30, 6625 (1989).CrossRefGoogle Scholar
  5. 5.
    D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, Tetrahedron Lett., 31, 5587 (1990).CrossRefGoogle Scholar
  6. 6.
    P. Kafarski, B. Lejcak, P. Mastalerz, Beitr. Wirt Forsh., H25 (1985).Google Scholar
  7. 7.
    K. M. Yagar, C. M. Taylor, J. Am. Chem. Soc., 116, 9377 (1994).CrossRefGoogle Scholar
  8. 8.
    L. C. Thomas, R. A. Chittenden, Chem. Ind. (London)., 1913 (1961).Google Scholar
  9. 9.
    F. W. Bennet, H. J. Emeleus, R. N. Haszeldine, J. Chem. Soc., 3598 (1954).Google Scholar
  10. 10.
    L. C. Thomas, The Interpretation of the Infrared Spectra of Organophosphorus Compounds, Heydon, Sons, London, 1974.Google Scholar
  11. 11.
    R. A. Chittenden, L. C. Thomas, Spectrochim. Acta, 22, 1449 (1966).CrossRefGoogle Scholar
  12. 12.
    R. M. Silverstein, G. C. Bassler, T. C. Morill, Spectrometric Identification of Organic Compounds, John Wiley and Sons, New York, 1991.Google Scholar
  13. 13.
    P. A. Odorisio, S. D. Pastor, J. D. Spivack, L. P. Steinhubel, R. K. Rodenbauch, Phosphorus, Sulfur, 15, 9 (1984).CrossRefGoogle Scholar
  14. 14.
    C. D. Reddy, R. S. N. Reddy, M. S. Reddy, M. Krishnaiah, K. D Berlin, P. Sunthankar, Phosphorus, Sulfur, Silicon, 63, 162 (1991).CrossRefGoogle Scholar
  15. 15.
    J. C. Locknart, M. B. Mc Donell, P. D. Tyson, J. Chem. Soc., Perkin Trans. 1, 2153 (1983).Google Scholar
  16. 16.
    G. C. Levy, J. D. Cargioli, J. Chem. Soc., 1663 (1970).Google Scholar
  17. 17.
    Q. N. Porter, J. Baldas, Mass Spectrometry of Heterocyclic Compounds, Wiley Intersci., New York, 1971, p. 16.Google Scholar
  18. 18.
    T. W. Rawlins, Phytopathological and Botanical Research Methods, John Wiley, Sons, New York, 1993, p. 156.Google Scholar
  19. 19.
    K. R. Aneja, Experiments in Microbiology Plant, Pathology and Tissue Culture, Wishwa Prakashan, New Delhi (A Division of Wiley Eastern Ltd.), 1993, p. 471.Google Scholar
  20. 20.
    S. C. Vyas, Handbook of Systemic Fungicides, Tata McGraw-Hill, Publ. Ltd., New Delhi, 1993, p. 206.Google Scholar
  21. 21.
    Y. Ogata, A. Kowasaki, Tetrahedron, 23, 2589 (1969).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • M. F. Stephen Babu
    • 1
  • B. Hari Babu
    • 1
  • K. R. Kishore Kumar Reddy
    • 1
  • C. Naga Raju
    • 1
  • C. Suresh Reddy
    • 1
  1. 1.Department of ChemistrySri Venkateswara UniversityIndia

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