Electrooxidative cyclization of N-acylhydrazones of aldehydes and ketones to .DELTA.3-1,3,4-oxadiazolines and 1,3,4-oxadiazoles
摘要:
The electrolytic oxidation of ketone N-acylhydrazones (1) in methanolic sodium acetate induced their intramolecular cyclization to the corresponding 2-methoxy-DELTA(3)-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.
Epoxyethers. IX. Acid-catalyzed Rearrangements<sup>1</sup>
作者:Calvin L. Stevens、Stanley J. Dykstra
DOI:10.1021/ja01646a039
日期:1954.9
Epoxyethers. XIV.<sup>1,2</sup> The Reaction with Grignard Reagents without Rearrangement
作者:CALVIN L. STEVENS、WILLIAM HOLLAND
DOI:10.1021/jo01100a001
日期:1958.6
Epoxyethers. II. The Epoxyether from α-Halocyclohexyl Phenyl Ketone<sup>1</sup>
作者:Calvin L. Stevens、Eugene Farkas
DOI:10.1021/ja01123a012
日期:1952.2
Electrooxidative cyclization of N-acylhydrazones of aldehydes and ketones to .DELTA.3-1,3,4-oxadiazolines and 1,3,4-oxadiazoles
作者:Toshiro Chiba、Mitsuhiro Okimoto
DOI:10.1021/jo00031a014
日期:1992.2
The electrolytic oxidation of ketone N-acylhydrazones (1) in methanolic sodium acetate induced their intramolecular cyclization to the corresponding 2-methoxy-DELTA(3)-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.
Synthesis and Antitremorine Activity of Amino Ketals