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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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References

  1. P. Kafarki, B. Lejezak, Phosphorus, Sulfur, Silicon, 63, 193 (1991).

    Article  Google Scholar 

  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. S. K. Chung, D. O. Kang, Tetrahedron: Asymmetry, 7, 21 (1996).

    Article  CAS  Google Scholar 

  4. B. Stowasser, K. H. Budt, L. Jian-Qi, A. Peyman, D. Ruppert, Tetrahedron Lett., 30, 6625 (1989).

    Article  Google Scholar 

  5. D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, Tetrahedron Lett., 31, 5587 (1990).

    Article  CAS  Google Scholar 

  6. P. Kafarski, B. Lejcak, P. Mastalerz, Beitr. Wirt Forsh., H25 (1985).

  7. K. M. Yagar, C. M. Taylor, J. Am. Chem. Soc., 116, 9377 (1994).

    Article  Google Scholar 

  8. L. C. Thomas, R. A. Chittenden, Chem. Ind. (London)., 1913 (1961).

  9. F. W. Bennet, H. J. Emeleus, R. N. Haszeldine, J. Chem. Soc., 3598 (1954).

  10. L. C. Thomas, The Interpretation of the Infrared Spectra of Organophosphorus Compounds, Heydon, Sons, London, 1974.

    Google Scholar 

  11. R. A. Chittenden, L. C. Thomas, Spectrochim. Acta, 22, 1449 (1966).

    Article  CAS  Google Scholar 

  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. P. A. Odorisio, S. D. Pastor, J. D. Spivack, L. P. Steinhubel, R. K. Rodenbauch, Phosphorus, Sulfur, 15, 9 (1984).

    Article  Google Scholar 

  14. C. D. Reddy, R. S. N. Reddy, M. S. Reddy, M. Krishnaiah, K. D Berlin, P. Sunthankar, Phosphorus, Sulfur, Silicon, 63, 162 (1991).

    Article  Google Scholar 

  15. J. C. Locknart, M. B. Mc Donell, P. D. Tyson, J. Chem. Soc., Perkin Trans. 1, 2153 (1983).

  16. G. C. Levy, J. D. Cargioli, J. Chem. Soc., 1663 (1970).

  17. Q. N. Porter, J. Baldas, Mass Spectrometry of Heterocyclic Compounds, Wiley Intersci., New York, 1971, p. 16.

    Google Scholar 

  18. T. W. Rawlins, Phytopathological and Botanical Research Methods, John Wiley, Sons, New York, 1993, p. 156.

    Google Scholar 

  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. S. C. Vyas, Handbook of Systemic Fungicides, Tata McGraw-Hill, Publ. Ltd., New Delhi, 1993, p. 206.

    Google Scholar 

  21. Y. Ogata, A. Kowasaki, Tetrahedron, 23, 2589 (1969).

    Article  Google Scholar 

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Correspondence to C. Suresh Reddy.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, 1574–1580, September, 2007.

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Babu, M.F.S., Babu, B.H., Reddy, K.R.K.K. et al. Syntheses of substituted 8-(aminobenzyl)dinaphthodioxaphosphocine 8-oxides. Chem Heterocycl Comp 43, 1336–1341 (2007). https://doi.org/10.1007/s10593-007-0203-x

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