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Zur Synthese von Alkoxymethylenmalonitrilen, Tetracyanpropeniden und hochsubstituierten α-Aminopyridinen

Syntheses with nitriles, XLVI: Synthesis of alkoxymethylene-malononitriles, tetracyanopropenides and substituted α-aminopyridines

Synthesen mit Nitrilen, 46. Mitt.

  • Organische Chemie und Biochemie
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Abstract

Malononitrile reacts with triethyl orthoformate,-orthoacetate,-orthopropionate and-orthobenzoate, resp., in the presence of different amounts of pyridine to ethoxymethylene-malononitriles and pyridinium 1,1,3,3-tetracyano-propenides, resp. The latter can easily be cyclised to 2-amino-6-chloro-3,5-dicyano-(4-alkyl and aryl, resp.)-pyridines. The synthesis of the α-aminopyridines can be carried out as one step reactions starting with malononitrile and orthoformate.

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Literatur

  1. T. Passalacqua, Gazz. Chim. Ital.43, Part II, 566 (1913).

    Google Scholar 

  2. R. G. Jones, J. Amer. Chem. Soc.74, 4889 (1952).

    Google Scholar 

  3. O. Diels, H. Gärtner undR. Kaak, Ber. dtsch. Chem. Ges.55, 3441 (1922).

    Google Scholar 

  4. W. Huber, J. Amer. Chem. Soc.65, 2224 (1943).

    Google Scholar 

  5. A. Ishiwata, Takamine Kenkyusho Nempo9, 21–25 (1957); Chem. Abstr.55, 1439d.

    Google Scholar 

  6. C. C. Cheng undR. Robins, J. Org. Chem.21, 1240 (1956).

    Google Scholar 

  7. W. Huber undA. Hölscher, Ber. dtsch. chem. Ges.71 B, 87 (1938).

    Google Scholar 

  8. Y. Urushibara undM. T. Bayashi, Bull. Chem. Soc. Japan11, 557 (1936).

    Google Scholar 

  9. M. A. Call, J. Org. Chem.27, 2433 (1962).

    Google Scholar 

  10. W. Whitehead undJ. J. Traverso, J. Amer. Chem. Soc.78, 5294 (1956).

    Google Scholar 

  11. E. C. Taylor undE. E. Garcia, J. Org. Chem.29, 2116 (1964).

    Google Scholar 

  12. M. Nishimura, K. Ito, M. Tsurushima undN. Inone, Takeda Chemical Industries; Jap. Pat. 15 961 (1964); Chem. Abstr.62, 10344d (1965).

  13. L. Nicholl, P. J. Tarsio undH. Blohm, US-Pat. 2 824 121 (1948); Chem. Abstr.52, 11909 (1958).

  14. Y. Urushibara, Bull. Chem. Soc. Japan2, 278 (1927).

    Google Scholar 

  15. E. L. Little, jr., W. J. Middleton, D. D. Coffman, V. A. Engelhardt undG. N. Sausen, J. Amer. Chem. Soc.80, 2832 (1958).

    Google Scholar 

  16. L. Claisen, Ann. Chem.297, 1 (1897).

    Google Scholar 

  17. S. G. Dent undL. G. S. Brooker, US-Pat. 2 533 206 (1950); Chem. Abstr.55, 3272 (1851).

  18. T. Ogata, R. Tanno undK. Nsihida, Rept. Sci. Res. Inst. (Tokio)28, 259 (1952); Chem. Abstr.47, 5284 (1953).

    Google Scholar 

  19. A. Dornow undE. Schleese, Chem. Ber.91, 1830 (1958).

    Google Scholar 

  20. G. N. Sausen, V. A. Engelhardt undW. J. Middleton, J. Amer. Chem. Soc.80, 2815 (1958).

    Google Scholar 

  21. J. P. Vila undR. G. Jarque, Anales fis. y quim. [Madrid]40, 946 (1944); Chem. Abstr.39, 4329 (1945).

    Google Scholar 

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Werner Schmidt, H., Junek, H. Zur Synthese von Alkoxymethylenmalonitrilen, Tetracyanpropeniden und hochsubstituierten α-Aminopyridinen. Monatshefte für Chemie 108, 895–900 (1977). https://doi.org/10.1007/BF00898055

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  • DOI: https://doi.org/10.1007/BF00898055

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