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Communication | Regular issue | Vol 3, No. 7, 1975, pp.557-562
Published online, 1st January, 1970
DOI: 10.3987/R-1975-07-0557
Compounds Related to Acridine. XII. Reaction of 1-(9-Acridinyl)-2-benzoylethylene and 9-Acridinylstyrylketone with Hydrazines

Akiyoshi Torii and Otohiko Tsuge*

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan

Abstract

The reaction of 1-(9-acridinyl)-2-benzoylethylene (1) with hydrazine hydrate (3) gave pyrazoline 4, hydrazinohydrazone 6, or pyrazole 7, depending on the reaction conditions. On the other hand, 9-acridinylstyrylketone (2) reacted with 3 under mild conditions to yield a Michael type adduct 8 as the main product, accompanied with hydrazinohydrazone 9 and 7. On heating in ethanol 8 was dissociated into starting materials. The reaction of 1 with phenylhydrazines (10) gave the expected pyrazolines 11, which on oxidation with lead tetraacetate gave pyrazoles 12, while 2 reacted with 10a to afford a Michael type adduct 13, which on heating in ethanol converted into 2 and 10a.