Journal of Organic Chemistry p. 1375 - 1379 (1992)
Update date:2022-07-30
Topics:
Chiba, Toshiro
Okimoto, Mitsuhiro
The electrolytic oxidation of ketone N-acylhydrazones (1) in methanolic sodium acetate induced their intramolecular cyclization to the corresponding 2-methoxy-Δ3-1,3,4-oxadiazolines 3.The thermal stability of a given oxadiazoline and what products were formed by its thermal decomposition was found to depend on the natures of the substituents at C-2.Thus, 2-methoxy-2-phenyloxadiazolines preferentially yielded oxiranes 5, whereas 2-alkyl-2-methoxyoxadiazolines preferentially gave enol ethers 6. 2,2-Dimethoxyoxadiazolines decomposed to the parent ketones and many unidentified products.The electrolytic oxidation of aldehyde N-acylhydrazones 2 gave 2,5-disubstituted 1,3,4-oxadiazoles 4.The oxidative cyclization of the N-benzoylhydrazones of aliphatic aldehydes gave especially high yields of the corresponding heterocycles.
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