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Reaction of N-aminomethylamides of carboxylic acids with phosphorous acid esters

  • Organic and Biological Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A method was developed for the preparation of the esters of N-acylaminomethylphosphonic acids by the reaction of the N-dialkylaminomethylamides of monobasic acids with trialkyl phosphites.

  2. 2.

    The reaction of N-dimethylaminomethylphthalimide with trialkyl phosphites in the presence of a salt-forming agent, which has a labile hydrogen atom, proceeds with the formation of the esters of dimethyl-aminomethylphosphonic acid. Salt-forming agents of the alkyl halide type lead to the formation of the ester of N-phthalimidomethylphosphonic acid.

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Literature cited

  1. M. I. Kabachnikand T. Ya. Medved', Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1126 (1953); 327, 687 (1956).

  2. A. N. Pudovik, É. I. Kashevarova, and N. G. Khusainova, Dokl. Akad. Nauk SSSR,145, 818 (1962).

    Google Scholar 

  3. V. Chavane, Compt. Rend.,224, 406 (1947); Bull. Soc. Chim. France, 774 (1948).

    Google Scholar 

  4. M. Chalmers and G. M. Kosolapoff, J. Am. Chem. Soc.,75, 5278 (1953).

    Google Scholar 

  5. J. K. Chambers and A. F. Isbell, J. Org. Chem.,29, 832 (1964).

    Google Scholar 

  6. H. Hellman, Angew. Chem.,69, 463 (1957).

    Google Scholar 

  7. J. Ugelstad and J. De Jonge, Rec. Trav. Chim.,76, 919 (1957).

    Google Scholar 

  8. N. H. Cromwell and D. J. Cram, J. Am. Chem. Soc.,65, 301 (1943).

    Google Scholar 

  9. H. R. Snyder and J. H. Brewster, J. Am. Chem. Soc.,70, 4230 (1948).

    Google Scholar 

  10. J. H. Brewster and E. L. Eliel, Organic Reactions [Russian translation], Vol. 7, IL (1956), p. 169.

  11. R. G. Harvey, Tetrahedron,22, 2562 (1966).

    Google Scholar 

  12. B. A. Arbuzov, V. S. Vinogradova, O. D. Zolova, and Yu. Yu. Samitov, Dokl. Akad. Nauk SSSR,173, 335 (1967).

    Google Scholar 

  13. K. M. Kirillova and V. A. Kukhtin, Zh. Obshch. Khim.,35, 544 (1965).

    Google Scholar 

  14. N. P. Gambaryan, Yu. A. Cheburkov, and I. A. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 1526 (1964).

  15. F. Ramirez, A. V. Patwardhan, and C. P. Smith, J. Org. Chem.,31, 474 (1966).

    Google Scholar 

  16. F. Ramirez, S. B. Bhatia, A. V. Patwardhan, and C. P. Smith, J. Org. Chem.,32, 3547 (1967).

    Google Scholar 

  17. C. W. Sauer and R. Bruni, J. Am. Chem. Soc.,77, 2559 (1955).

    Google Scholar 

  18. B. E. Ivanov, S. S. Krokhina, and A. V. Chernova, Izv. Akad. Nauk SSSR, Ser. Khim., 606 (1968).

  19. B. A. Arbuzov and V. S. Vinogradova, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 459 (1947).

  20. Dictionary of Organic Compounds [Russian translation], IL (1949).

  21. H. Böhme and K. H. Meyer-Dulheuer, Ann. Chem.,688, 91 (1965).

    Google Scholar 

  22. V. Jagodic, Chem. Ber.,93, 2308 (1960).

    Google Scholar 

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2493–2499, November, 1971.

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Ivanov, B.E., Krokhina, S.S. Reaction of N-aminomethylamides of carboxylic acids with phosphorous acid esters. Russ Chem Bull 20, 2364–2368 (1971). https://doi.org/10.1007/BF00854314

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  • DOI: https://doi.org/10.1007/BF00854314

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