The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reactivity of the flavanone nucleus. II. Effect of substituents on the reaction with phenylhydrazine》. Authors are Venturella, Pietro.The article about the compound:1,5-Diphenyl-1H-pyrazole-3-carboxylic acidcas:13599-22-9,SMILESS:OC(=O)C1=NN(C(=C1)C1=CC=CC=C1)C1=CC=CC=C1).Recommanded Product: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid. Through the article, more information about this compound (cas:13599-22-9) is conveyed.
cf. CA 55, 15467b. Substituents in the flavanone nucleus do not particularly affect the conversion of their phenylhydrazones into pyrazoline derivatives The possibility to isolate the intermediate phenylhydrazones depends on the nature and the position of the substituents. The appropriate flavanone (0.5 g.) in 10 cc. 95% EtOH refluxed 1 hr. with 0.3 g. PhNHNH2, kept some time, and diluted with H2O gave the corresponding phenylhydrazone. In this manner were prepared the following compounds: 2-(p-methoxyphenyl)flavanone phenylhydrazone (I); 2-[3,4-(CH2O2)C6H3] analog (II) of I, m. 127-8°; 2-(3,4-methyl-enedioxyphenyl)-5,6,8-trimethoxyflavanone phenylhydrazone (III) (without EtOH), m. 129-31°; 2-Ph analog of III; 2-phenyl-6-methoxyflavanone phenylhydrazone (IV); and the 5,6-di-MeO analog of IV, needles, m. 118-20°. The appropriate flavanone (0.5 g.) and excess PhNHNH2 heated a few min. in a test tube over a free flame, cooled, dissolved in AcOH, and poured into H2O gave the corresponding 3,5-diarylpyrazoline (V). The appropriate flavanone (0.5 g.) in 5 cc. AcOH refluxed 1 hr. with 0.3 g. PhNHNH2, cooled, and diluted with H2O gave the corresponding V. The appropriate chalcone (0.2 g.) and PhNHNH2 heated a few min. in a test tube over a free flame, dissolved in AcOH, and poured into H2O gave the corresponding V. The appropriate phenylhydrazone refluxed 1 hr. with AcOH gave the corresponding V. The appropriate V refluxed with Ac2O and NaOAc gave the corresponding acetate which fluoresces in EtOH intensely blue-green. By these methods were prepared the following V and their acetates (3- and 5-aryl group, crystal form, and m.p., and m.p. of acetate given): o-HOC6H4, p-MeOC6H4 (Va), needles, 168-9°, 132-3°; o-HOC6H4, 3,4-(CH2O2)C6H3 (VI), needles, 145-6°, 116-17°; 2,3,5,6-HO(MeO)3C6H, 3,4-(CH2O2)C6H3 (VIa), needles, 185-6°, 195-6°, 2,3,5,6-HO(MeO)3C6H, Ph (VII), yellow-green plates, 193-4°, 132-3°; 2,5-HO(MeO)C6H3, Ph (VIII), needles, 150-1°, 114-15°; 2,5,6-HO(MeO)2C6H2, Ph (IX), yellow plates, 147-8°, 147°, VII or VIII or IX (1 g.) in 30 cc. refluxing 5% aqueous NaOH treated gradually with 6.5 g. KMnO4 in 70 cc. H2O, refluxed 3 hrs., and worked up gave 1,5-diphenyl-3-pyrazolecarboxylic acid, m. 183-5° (EtOH). Va or VI, or Via oxidized similarly with 8 g. KMnO4 in 100 cc. H2O gave 1-phenyl-3,5-pyrazoledicarboxylic acid, platelets, m. 265-6° (H2O). The ultraviolet absorption spectra of the various pyrazolines, and II, III, and V, and the infrared absorption spectra of VI and its acetate are recorded.
《Reactivity of the flavanone nucleus. II. Effect of substituents on the reaction with phenylhydrazine》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(1,5-Diphenyl-1H-pyrazole-3-carboxylic acid)Recommanded Product: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid.
Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem