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Contributions to the study of some heterocycles. XLV. Configuration of the ketoximes of some substituted 4-acetyl-2-phenylthiazoles

H. Demian, S. Mager, I. Schwartz, and I. Simiti

Department of Organic Chemistry, Faculty of Pharmacy, 3400 Cluj-Napoca, Roumania


Abstract:  The configuration of the ketoximes of some 4-acetyl-2-(p-X-phenyI)-5-Y-thiazoles was studied. Chemical proofs (Beckmann rearrangement) confirmed by mass spectra and u.v. measurements demonstrate the and thiazole (E) configuration of the investigated oximes. The remarkable negative solvatochromy of the oxime Па, acetylated oxime VI, as well as of the ketones la—d, points out a particular behaviour of the proton in the position 5 of the thiazole ring, assigned to the existence of a weak С — H ---Z (Z = 0 , N) interaction. The 1H - n. m. r. spectra confirm the particularity of the H-5 proton and the study of the dependence of chemical shifts on concentration and temperature suggests a weak intramolecular hydrogen bond interaction bet­ween the oximic nitrogen and the heteroaromatic H-5 proton.

Full paper in Portable Document Format: 333a387.pdf


Chemical Papers 33 (3) 387–396 (1979)

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