Summary
The bifunctional title compounds2 react with acylating, carbamoylating and sulfonylating reagents mostly at the primary amino group of the hydrazine function. Both functional groups of2 are attacked by N,N′-carbonyldiimidazole converting it into 1H-1,2,4,5-tetrazepin-3-one derivatives8. The acid-induced 1,4-elimination of phenylhydrazine from2 gives rise to the formation of phenylosazones3. In the presence of thiocyanic acid the intermediately formed phenylazo-alkenes1 undergo [3+2]-cycloaddition furnishing 1-anilino-imidazoline-2-thiones13.
Zusammenfassung
Die bifunktionellen Titelverbindungen2 reagieren mit Acylierungs-, Carbamoylierungs-und Sulfinylierungs-Reagenzien meist an der primären Amino-Gruppe der Hydrazin-Funktion. N,N′-Carbonyldiimidazol greift beide funktionelle Gruppen von2 an und bedingt die Umwandlung in 1H-1,2,4,5-Tetrazepin-3-on-Derivate8. Die säureinduzierte 1,4-Eliminierung von Phenylhydrazin aus2 führt zur Bildung der Phenylosazone3. In Gegenwart von Thiocyansäure erfolgt [3+2]-Cycloaddition an die intermediär gebildeten Phenylazo-alkene1, sodaß 1-Anilino-imidazolin-2-thione13 entstehen.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References and Notes
Part IV: Schantl J. G., Karpellus P., Prean M. (1987) Tetrahedron43: 5807–5814
Schantl J. G., Karpellus P., Prean M. (1982) Tetrahedron38: 2643–2652
Simon H., Heubach G., Wacker H. (1967) Chem. Ber.100: 3106–3120. Simon H., Moldenhauer W. (1969) Chem. Ber.102: 1191–1197. Ref. cited therein
Schantl J. G., Hebeisen P. (1983) Sci. Pharm.51: 379–390
Prean M. (1981) Doctoral Thesis. University of Innsbruck
Schantl J. G., Hebeisen P., Karpellus P. (1989) Synth. Commun.19: 39–48
Iffland D. C., Salisbury L., Schafer W. R. (1961) J. Am. Chem. Soc.83: 747–749
Thesing J., Willersinn C. H. (1956) Chem. Ber.89: 1195–1203
Young G. W., Roberts J. D. (1946) J. Am. Chem. Soc.68: 649–652
Bloink G. J., Pausacker K. H. (1950) J. Chem. Soc. 1328–1331
Dutt P. K., Whitehead H. R., Wormall A. (1921) J. Chem. Soc.119: 2098–2094
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Schantl, J.G., Prean, M. Addition products of hydrazine derivatives to azo-alkenes, part V: The reaction of α-(1-phenylhydrazino)alkanone phyenylhydrazones with acids and acid derivatives. Monatsh Chem 124, 299–308 (1993). https://doi.org/10.1007/BF00810587
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00810587