{"id":11774,"date":"2022-12-02T03:56:09","date_gmt":"2022-12-01T19:56:09","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=11774"},"modified":"2022-12-02T03:56:09","modified_gmt":"2022-12-01T19:56:09","slug":"finar-i-l-s-team-published-research-in-journal-of-the-chemical-society-in-cas-13599-22-9","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=11774","title":{"rendered":"Finar, I. L.’s team published research in Journal of the Chemical Society in | CAS: 13599-22-9"},"content":{"rendered":"

Finar, I. L. published the artcilePreparation and properties of some bipyrazolyls<\/i><\/b>, Application of 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid<\/a>, the publication is Journal of the Chemical Society (1955), 1205-8, database is CAplus.<\/p>\n

The synthesis of 5,5′-dimethyl-1,1′-diphenyl-(I) and 1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl (II) was repeated, and the 3,5′-isomer (III) of the latter was isolated. Evidence was given for the orientations of these two isomers, and some 4,4′-disubstituted derivatives of I, II, and III were prepared (CO2<\/sub>Et)2<\/sub> (IV) (36.5 g.) and 29 g. dry Me2<\/sub>CO were added during 25 min. to NaOMe (from 12.5 g. Na) under Et2<\/sub>O at 0\u00b0, the mixture was stirred for 2 days to give 21-38% octane-2,4,5,7-tetraone (V), yellow needles, m. 120-1\u00b0 (from MeOH). IV (36.5 g.) and 1\/2 of 16 g. PhCOMe were similarly treated, the other 1\/2 added 4 hrs. later, and the mixture stirred 3 days to give 62-74% 1,6-diphenylhexane-1,3,4,6-tetraone (VI), yellow needles, m. 177-9\u00b0. V (3.4 g.) was heated with 4.3 g. PhNHNH2<\/sub> in HOAc for 1 hr. to give 3.4 g. I, buff needles, m. 141-2\u00b0. VI (47.2 g.) was similarly treated 3-4 hrs. with 34.6 g. PhNHNH2<\/sub> to give 35.2 g. II, m. 233\u00b0. The filtrate was diluted with H2<\/sub>O and then crystallized to yield 12.2 g. III, white needles, m. 135-6\u00b0. VI (58.8 g.) in HOAc was treated during 2.75 hrs. with 21.6 g. PhNHNH2<\/sub> in HOAc, heated for a further 1.25 hrs., and set aside for 2 days to give after fractional crystallization unchanged starting material, II, and 3-(\u03b1-benzoylacetyl)-1,5-diphenylpyrazole (VII), yellow needles, m. 164-6.5\u00b0. VII on oxidation with alk. KMnO4<\/sub> yielded 1,5-diphenylpyrazole-3-carboxylic acid (VIII), m. 185-6\u00b0. VII (2.9 g.) and 0.97 g. PhNHNH2<\/sub> in HOAc heated 1 hr., and kept at room temperature overnight gave 2.4 g. II and 1 g. III. The infrared spectra of II and III were complex and similar. In general, the lowering of the symmetry as in III increases the number of bands. III in the 1600-650 cm.-1<\/sup> region had 25 strong bands. Bischler’s method [Ber. 25, 3143(1892)] of preparing VIII was modified as follows: MeCOCH2<\/sub>CO2<\/sub>Et (30 g.) was refluxed 6 hrs. with 5.4 g. Na wire under Et2<\/sub>O, then 46 g. BzCH2<\/sub>Br in Et2<\/sub>O was added to maintain gentle reflux, then refluxed 2 hrs., and set aside overnight to give 56 g. AcCH(CH2<\/sub>Bz)CO2<\/sub>Et (IX) as a red oil. IX (12.4 g.) in EtOH was treated in the cold with 4.65 g. PhN2<\/sub>Cl, and then 16.4 g. NaOAc in H2<\/sub>O, the mixture set aside 24 hrs. in ice, and the oil which separated heated 15 min. with 6 g. NaOH in a little H2<\/sub>O to give 6.7 g. VIII. I in CHCl3<\/sub> was treated with Br at room temperature to yield 4,4′-dibromo-5,5′-dimethyl-1,1′-diphenyl-3,3′-bipyrazolyl, rods, m. 159-60\u00b0. 4,4′-Dibromo-1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl, plates, m. 272-3\u00b0. 4,4′-Dibromo-1,1′,3′,5-tetraphenyl-3,5′-bipyrazolyl, white rosettes, m. 200-1\u00b0. II (13.2 g.) in HOAc and 26 cc. concentrated HCl was heated 2 hrs. with 2.4 g. paraformaldehyde to give the 4,4′-bis(chloromethyl) derivative, white needles, (6.2 g.), m. 274-6\u00b0. I (3.14 g.) in HOAc was heated 0.5 hrs. with 6.37 g. HgAc2<\/sub> to yield 4.8 g. 4,4′-bis(acetoxymercuri) compound (X), white needles, m. 204-4.5\u00b0 (aqueous HOAc). II (4.38 g.) similarly treated yielded after 5 hrs. refluxing 7.6 g. 4,4′-bis(acetoxymercuri)-1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl (XI), white powder, m. 271.5\u00b0. The mercuri compounds when treated with HOAc and Br at room temperature gave the corresponding 4,4′-di-Br compounds X refluxed with dilute HCl gave I; however, XI had to be refluxed for some time with HOAc containing concentrated HCl before II could be obtained.<\/p>\n

Journal of the Chemical Society 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, Application of 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid<\/a>.<\/p>\n

Referemce:
https:\/\/en.wikipedia.org\/wiki\/Pyrazole<\/a>,
Pyrazoles – an overview | ScienceDirect Topics<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"

Journal of the Chemical Society 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, Application of 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid<\/a>.<\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[819,131],"tags":[740],"class_list":["post-11774","post","type-post","status-publish","format-standard","hentry","category-13599-22-9","category-pyrazoles-derivatives","tag-m-w250-300"],"yoast_head":"\nFinar, I. L.'s team published research in Journal of the Chemical Society in | CAS: 13599-22-9 | pyrazoles-derivatives<\/title>\n<meta name=\"description\" content=\"Finar, I. 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