Abstract
Aliphatic amidoximesR—C (NH2)=NOH react with diketene to yield 5-acetonyl-3-alkyl-1,2,4-oxadiazoles, which are susceptible to a wide variety of reactions at the keto-group as well as at the methylene-group. Their transformations into 1-methyl-2-oxadiazolyl-vinylN,N-dimethylcarbamates, 2-chloro-1-oxadiazolylpropenes, 1-oxadiazolyl-2-(1,2,4-triazol-1-yl)propenes, 1,1-dichloro-1-oxadiazolylacetones and 3-hydroxy-2-oxadiazolyl-crotonic amides are described as well as their reactions with diazonium salts, with sodium nitrite and with carbon disulfide. Further products obtained are carbamates of of 1-oxadiazolyl-2-oxo-propane-1-oximes, 2-chloro-2-oxadiazolylvinyl phosphates and an oxadiazolyl pyrimidine.
Similar content being viewed by others
Literatur
Sasaki T., Yoshioka T., Bull. Chem. Soc. Jap.42, 3008 (1969).
Tiemann F., Ber.22 II, 2414 (1889).
Weise J., Ber.22 II, 2427 (1889).
Schubart L. H., Ber.22 II, 2438 (1889).
Richter E., Ber.22 II, 2457 (1889).
Merchx R., Bull. Soc. Chim. Belg.58, 58 (1949).
Yale H. L., Spitzmiller E. R., J. Heterocycl. Chem.15, 1373 (1978).
Kübel B., unveröffentlichte Versuche.
DE-OS 30 10 319 vom 18. 3. 1980; Hoechst AG, Erf.Kübel B.,Waltersdorfer A.,Knauf W.,Sachse B.
Kübel B.,Waltersdorfer A.,Knauf W., Z. Naturforsch. (im Druck).
Merchx R., Chim. & Ind. (Paris)63, 453 (1952).
Z. B. mit Barbitursäure: DE-OS 27 19 733 (Ciba-Geigy) und DE-OS 24 05 732 (Bayer-AG).
Author information
Authors and Affiliations
Additional information
Herrn Prof. Dr.Klaus Weissermel zu seinem 60. Geburtstag.
Rights and permissions
About this article
Cite this article
Kübel, B. Neue acetonylsubstituierte Azole I. 5-Acetonyl-1,2,4-oxadiazole. Monatsh Chem 113, 781–792 (1982). https://doi.org/10.1007/BF00809019
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00809019