Synthesis of Vomipyrine

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Abstract

AN outstanding result of Wieland‘s long series of investigations of vomicine was the degradation of the alkaloid to a base, C15H16N2, termed vomipyrine1. This afforded yellow salts, and the spectrochemical behaviour clearly indicated its constitution as an alkylated pyrroquinoline, C11H7N2.C4H9, although the position of fusion of the rings and the position and distribution of the alkyl group or groups (2Et, Me, Pr, Bu, etc.) was unknown. Guesses based on the earlier strychnine formulæ were disproved by synthesis2.

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References

  1. 1

    Wieland, H., and Horner, L., Annalen, 528, 73 (1937).

  2. 2

    Horner, L., Annalen, 540, 73 (1939); cf. ref. 9.

  3. 3

    Robinson, R., Experientia, 2, 28 (1946). Openshaw, H. T., and Robinson, R., Nature, 157, 438 (1946). Chakravarti, R. N., and Robinson, R., Nature, 160, 18 (1947).

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    Pausacker, K. H., and Robinson, R., J. Chem. Soc. (in the press, 1948).

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    Perkin, W. H., Robinson, R., and Smith, J. C., J. Chem. Soc., 1239 (1932).

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    Bailey, A. S., and Robinson, R., Nature, 161, 433 (1948).

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    Bradford, L., Elliott, T. J., and Rowe, F. M., J. Chem. Soc., 437 (1947).

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    Kyker, G. C., and Bost, R. W., J. Amer. Chem. Soc., 61, 2469 (1939).

  9. 9

    Wieland, H., and Horner, L., Annalen, 536, 89 (1938); cf. ref. 2.

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ROBINSON, R., STEPHEN, A. Synthesis of Vomipyrine. Nature 162, 177–178 (1948) doi:10.1038/162177a0

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