Venturella, Pietro published the artcileReactivity of the flavonic ring. I. Action of phenylhydrazine, Computed Properties of 13599-22-9, the publication is Annali di Chimica (Rome, Italy) (1961), 34-44, database is CAplus.
A pyrazoline derivative, C21H18ON2 was obtained from flavanone (I) by action of NH2NHPh (II) and its structure was studied by an oxidizing demolition and a direct synthesis. Pure I (0.5 g.) in 5 cc. AcOH was treated with 0.3 g. II to yield after 12 hrs. at room temperature the phenylhydrazone (III), m. 146-7° (EtOH). I (0.5 g.) in 5 cc. AcOH and 0.3 g. II, refluxed 1 hr., the mixture cooled, filtered, and the product crystallized (EtOH) gave 3-(o-hydroxyphenyl)-1,5-diphenylpyrazoline (IV), m. 164-5°. I and II, melted in a test tube, gave IV. 2-Hydroxychalcone (V) (0.5 g.) in 10 cc. AcOH with 0.35 g. II after 2-3 days at room temperature gave IV. V (1 g.) in 15 cc. EtOH refluxed 3 hrs. with 0.6 g. II, cooled, and the product crystallized (EtOH) gave IV. V (0.2 g.) melted with II in excess gave IV. IV (0.5 g.) with 5 cc. Ac2O and 1 g. AcOMe refluxed 1.5 hrs., poured into H2O, and the product crystallized gave 3-(o-acetoxyphenyl)-1,5-diphenylpyrazoline (VI), m. 111-12°. 3-(o-Hydroxy-phenyl)-1,5-diphenylpyrazole (VII), m. 105-6°, was prepared from o-hydroxydibenzoylmethane and II. Analogously was prepared 5-(o-hydroxyphenyl)-1,3-diphenylpyrazole (VIII), m. 162-3°. VII (1 g.) in 20 cc. EtOH with metallic Na in excess refluxed 2 hrs. and the product crystallized gave IV. Boiling 1 g. IV in 30 cc. 0.5N NaOH with 7 g. KMnO4 in 50 cc. H2O gave 1,5-diphenyl-3-pyrazolecarboxylic acid. Ultraviolet and infrared spectra of IV, VI, VII and VIII were given.
Annali di Chimica (Rome, Italy) published new progress about 13599-22-9. 13599-22-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Carboxylic acid,Benzene, name is 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid, and the molecular formula is C18H26ClN3O, Computed Properties of 13599-22-9.
Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics