Abstract
The oxidation of 6-β-[(hexahydro-1H-azepin-1-yl)methyleneamino]penicillanic acid with potassium periodate or m-chloroperbenzoic acid leads to the corresponding sulfoxide. Its structure was proved by alternative synthesis by splitting out the N-phenylacetyl group from the benzylpenicillin sulfoxide and condensation of the 6-aminopenicillanic acid sulfoxide with N-formylhexamethyleneimine dibutylacetal.
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R. D. G. Cooper, P. V. De Marco, J. C. Cheng, and N. D. Jones, J. Am. Chem. Soc., 91, 1408 (1969).
R. D. G. Cooper, P. V. De Marco, and D. O. Spry, J. Am. Chem. Soc., 91, 1528 (1969).
Koniklijke Nederlandishe Gist-en Spiritus-Fabriek N. V., Dutch Patent No. 2107650; Chem. Abstr., 76, 3879 (1972).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 649–651, May, 1982.
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Veinberg, G.A., Belevich, E.M. & Lukevits, É.Y. Structure of 6-β-[(hexahydro-1H-azepin-1-yl)methyleneamino]penicillanic acid sulfoxide. Chem Heterocycl Compd 18, 489–491 (1982). https://doi.org/10.1007/BF00526083
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DOI: https://doi.org/10.1007/BF00526083