Lapkin, I. I. published the artcileEsters of oxo acids of acetylene series. VI. Reaction of the esters of phenylethynylglyoxalic acid with hydrazine, hydrazide, and hydroxylamine, Product Details of C16H12N2O2, the publication is Zhurnal Organicheskoi Khimii (1966), 2(11), 2075-8, database is CAplus.
cf. CA 65, 10523b. Addition of N2H4.H2O to Et phenylethynylglyoxalate in EtOH gave 75% Et 3-phenylpyrazole-5-carboxylate, m. 139.5°; similarly were prepared: Pr ester, m. 110°; iso-Pr ester, m. 164°. Addition of RNHNH2 in Et2O to the appropriate ester of phenylethynylglyoxalic acid gave the following esters of 4-arylhydrazino-4-phenyl-3-buten-2-on-1-oic acids, RNHNHCPh:CCOCO2R’ (R and R’ shown, resp.): Ph, Et, 32%, m. 83°; Ph, iso-Pr (I) 65%, m. 124.5°; p-MeC6H4, iso-Pr, 32%, m. 77°; 0-MeC6H4, iso-Pr, 55%, m. 72.5°; Bz, iso-Pr (II) 87%, m. 125.5°; 0-O2NC6H4CO, iso-Pr, 78%, m. 137°; m-O2NC6H4CO, iso-Pr, 83%, m. 181°; p-O2NC6H4CO, iso-Pr, 88%, m. 175°. II heated in AcOH 2 hrs. gave 93% 1,5-diphenylpyrazole-3-carboxylic acid iso-Pr ester, m. 86.5-7°. I heated with aqueous alc. KOH 20 min. gave 1,5-diphenylpyrazole-3-carboxylic acid. Heating iso-Pr phenylethynylglyoxalate with HONH2.HCl in aqueous EtOH gave after addition of aqueous Na2CO3 over 9 hrs. 50% iso-Pr 3-phenylisoxazole-5-carboxylate, m. 65-6°. Similarly was prepared 29% Et 3-phenylisoxazole-5-carboxylate, m. 47°. Ir spectra were reported.
Zhurnal Organicheskoi Khimii 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 C16H12N2O2, Product Details of C16H12N2O2.
Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics