Month: December 2022

Cusmano, Sigismondo published the artcileTransformation of 3-isoxazolecarboxylic acids into pyrazole derivatives. IV, HPLC of Formula: 13599-22-9, the publication is Gazzetta Chimica Italiana (1940), 227-35, database is CAplus.

cf. C. A. 34, 7903.8. The transformation of 3-isoxazolecarboxylic acids into pyrazolonimines by fusion with PhNHNH₂ may proceed by decarboxylation followed by ring closure of the resulting cyano ketone phenylhydrazone. To test this hypothesis the fusion was repeated in the presence of Natur Kupfer C (I) (or ordinary reduced Cu) so that, at the lower decarboxylation temperatures it might be possible to isolate the phenylhydrazone prior to ring closure and so shed some light on the mechanism of the reaction. A mixture of 1 g. of 5-phenyl-3-isoxazolecarboxylic acid (II), 1 g. I and 1 g. PhNHNH₂ in 20 cc. alc. was boiled for a few min. over a free flame, filtered, alkalinized with Na₂CO₃, extracted free from PhNHNH₂ with ether, acidified with dilute H₂SO₄, and extracted with ether. The residue from the evaporated extract gave 1,5-diphenyl-3-pyrazolecarboxylic acid (III), m. 185° (Et ester, m. 98°), decarboxylated by fusion to give 1,5-diphenylpyrazole, m. 55°, and identical with the known acid prepared by the action of PhNHNH₂ on BzCH₂COCO₂H. A similar transformation of 5-methyl-3-isoxazolecarboxylic acid (IV) gave 1-phenyl-5-methyl-3-pyrazolecarboxylic acid, m. 136° (Me ester, m. 55°), decarboxylated to 1-phenyl-5-methylpyrazole, transformed into the known picrate, m. 98°. In these transformations alc. can be replaced by other solvents. In the absence of I or in the presence of PhNH₂ instead of PhNHNH₂ the isoxazolecarboxylic acid is recovered unchanged.

Gazzetta Chimica Italiana 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, HPLC of Formula: 13599-22-9.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Chaudhari, Parthiv Kantilal published the artcileSynthesis and biological evaluation of 4,5-dihydro-4-(1-aryl-3-methyl-5-chloro-1h-pyrazol-4-yl)-1-phenyl-3-methyl-1H-pyrazolo[3,4-d]pyrimidine-6-thiol, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is Journal of Ultra Chemistry (2012), 8(1), 41-48, database is CAplus.

The synthesis of 4,5-dihydro-4-(4,5-dihydro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-aryl-3-methyl-1H-pyrazolo[3,4-d]pyrimidine-6-thiol were undertaken by the condensation of 1-aryl 3-methyl-1H-pyrazol-5(4H)-one with thiourea and 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde. The constitution of the products were characterized by using elemental anal. IR, 1 NMR and mass spectral data. The products were assayed for their in vitro biol. assay like antibacterial activity towards gram pos. and Gram neg. bacterial strain and antifungal activity towards Aspergillus nigor MICC-282 and Candida albicans MTCC-227 at a concentration of 40 μg/mL.

Journal of Ultra Chemistry published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Arnold, Z. published the artcileSynthetic reactions of dimethylformamide. XVI. Formylalion of γ-picoline, SDS of cas: 19959-71-8, the publication is Collection of Czechoslovak Chemical Communications (1963), 863-8, database is CAplus.

cf. CA 59, 439h. Treatment of γ-picoline (I) with (Me₂NCH:NMe₂)⁺ClO₄^– (II) gave 4-(β-dimethylaminovinyl)pyridine (III) which reacted with IICONMe₂ (DMF) and COCl₂ to give α-(4-pyridyl)-β-dimethylaminoacrolein (IV), also obtained by treatment of I with DMF and COCl₂ or POCl₃. Alk. hydrolysis of IV afforded 4-pyridylmalonic dialdehyde (V). V with N₂H₄ gave 4-(4-pyridyl)pyrazole (VI), with H₂NCONHNH₂ (VII), 4-(4-pyridyl)pyrazole-1-carboxamide (VIII), with H₂NCSNHNH₂ (IX), α-(4-pyridyl)-β-thiosemicarbazinoacrolein (X), and with NH₃, 5-(4-pyridyl)pyrimidine (XI). To a mixture obtained from 0.26 g. Na and 100 ml. liquid NH₃, 1.86 g. I was added at -60°, followed, after 15 min., by 4 g. powd. II. After cooling and stirring for 15 addnl. min., the NH₃ was evaporated, the residue treated with 20 ml. C₆H₆ and 3 ml. H₂O, the aqueous layer extracted with C₆H₆, the extract washed with H₂O, dried, filtered, and evaporated to give 1.55 g. (52%) III, m. 101-2° (MeCOEt at -60°). Adding 1.5 g. III to a solution prepared by adding 5 ml. 3N COCl₂ in CHCl₃ to 3.65 g. DMF in 25 ml. CHCl₃, stirring the mixture 30 min. at room temperature, refluxing 6 hrs., treating with a saturated solution of K₂CO₃, extracting with 1:1 C₆H₆-EtOH, evaporating, and extracting the residue with C₆H₆ gave 1.4 g. (79%) IV, R_f 0.65 (Whatman Number 4 paper in MeCOEt-H₂O), m. 90-2° (MeCOEt at -70°), also obtained by adding 1.86 g. I to a reagent prepared from 21.9 g. DMF and 9.2 g. POCl₃, heating the mixture 6 hrs. at 70°, adding it to 70 ml. saturated solution of K₂CO₃ covered with 30 ml. 1:1 C₆H₆EtOH, filtering the salts, extracting the filtrate with the above mixture, drying the extract with anhydrous K₂CO₃, evaporating, extracting the residue with C₆H₆, and evaporating to dryness in vacuo, yield 3.2 g. (91%) crude, 2.4 g. (68%) pure. IV was also obtained in 51% yield by stirring a mixture of 0.93 g. I in 3 ml. CHCl₃, 7.3 g. DMF in 25 ml. CHCl₃, and 10 ml. 3N COCl₂ in CHCl₃ 1 hr. at room temperature and 5 hrs. at reflux. Heating 0.176 g. IV with 0.11 g. 50% KOH and a few drops H₂O to 70°, cooling the mixture, precipitating with concentrated KOH a potassium salt of V, filtering it off with suction, dissolving in H₂O, and acidifying the solution gave V, m. >320° (H₂O), also obtained in 80% yield by heating a mixture of 21.9 g. DMF, 9.2 g. POCl₃, and 1.86 g. I 6 hrs. at 70°, cooling, treating with 70 g. ice and a solution of 12 g. NaOH in 20 ml. H₂O at 20°, heating the mixture 10 min. at 90°, cooling, and acidifying with 1:1 HCl to pH 7. Treatment of 0.15 g. V with an equal amount of 90% N₂H₄ afforded VI, m. 198-9° (H₂O). Mixing a solution of 0.15 g. V in 6 ml. N HCl with a solution of 0.11 g. VII.HCl in 3 ml. N HCl gave VIII, m. 230°. Similar treatment of V with 0.09 g. IX gave X, m. 200°. Heating 0.3 g. V with 10 ml. NH₃ in EtOH 3 hrs. at 120° in a stainless steel autoclave, filtering the mixture with activated C, and evaporating in vacuo gave 0.12 g. XI, m. 107.5-8.5° (MeCOEt).

Collection of Czechoslovak Chemical Communications published new progress about 19959-71-8. 19959-71-8 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Pyridine, name is 4-(1H-Pyrazol-4-yl)pyridine, and the molecular formula is C8H7N3, SDS of cas: 19959-71-8.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Anonymous published the artcileCrystalline forms of intermediates used in the preparation of (3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide and its salts, COA of Formula: C6H3ClN4O2, the publication is IP.com Journal (2019), 19(4A), 1-11, database is CAplus.

Synthesis and crystallinity of intermediates used in the preparation of (3S)-N-[5[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide and its salts was reported.

IP.com Journal published new progress about 1363380-51-1. 1363380-51-1 belongs to pyrazoles-derivatives, auxiliary class Other Aromatic Heterocyclic,Chloride,Nitro Compound, name is 5-Chloro-3-nitropyrazolo[1,5-a]pyrimidine, and the molecular formula is C6H3ClN4O2, COA of Formula: C6H3ClN4O2.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Zhang, Jingshun published the artcileCombination of experimental and theoretical methods to explore the amino-functionalized pyrazolium ionic liquids: An efficient single-component catalyst for chemical fixation of CO₂ under mild conditions, Synthetic Route of 930-36-9, the publication is Molecular Catalysis (2019), 37-45, database is CAplus.

Four new amino-functionalized pyrazolium ionic liquids, I [R = Me, Et; n = 1, 2] were firstly synthesized in simple reaction steps with cheap raw materials. Ionic liquids I would catalyze the coupling reaction of carbon dioxide with propyleneoxide under optimal reaction conditions, 110 °C, 1.5 MPa carbon dioxide initial pressure as well as 1.0 mol% catalyst amount for 4.0 h, with propylene carbonate yield over 94%. The reaction temperature was decreased by 10-20 °C as compared with other single-component ionic liquids and at the same time, carbon dioxide initial pressure was not increased to keep 1.5 MPa. The recyclability and suitability of amino-functionalized pyrazolium ionic liquids were explored and catalytic mechanism was investigated by d. functional theory. Moreover, the influence of weak interactions on reaction was analyzed by atoms in mols. and non-covalent interactions. As compared with other reported ionic liquids, the reaction condition catalyzed by ionic liquid I [R = Et, n = 2] was more benign with comparable product yield. More importantly, there was good balance among various reaction conditions without sacrificing one to ensure others.

Molecular Catalysis published new progress about 930-36-9. 930-36-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole, name is 1-Methylpyrazole, and the molecular formula is C8H8O3, Synthetic Route of 930-36-9.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Zhao, Hui published the artcileN-alkylation of N-H compounds in N, N-dimethylformamide dialkyl acetal, Synthetic Route of 930-36-9, the publication is Youji Huaxue (2019), 39(2), 434-442, database is CAplus.

The N, N-dimethylformamide dialkyl acetal was used as the alkyl source to achieve different nitrogen alkylation reactions of N-H compounds The reaction has the advantages of cheap raw materials, easy operation, mild reaction conditions, broad substrate scope and no metal participation. By studying the effects of solvents, temperature, reaction time, and the amount of N, N-dimethylformamide dialkyl acetal on the reaction, the optimal reaction conditions were obtained. The effect of different N, N-dimethylformamide dialkyl acetals on the alkylation ability of the substrate was investigated.

Youji Huaxue published new progress about 930-36-9. 930-36-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole, name is 1-Methylpyrazole, and the molecular formula is C18H15N3O3, Synthetic Route of 930-36-9.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Igarashi, Mami published the artcileCatalytic oxidation of 2,4,6-tribromophenol using iron(III) complexes with imidazole, pyrazole, triazine and pyridine ligands, Recommanded Product: 1-Methylpyrazole, the publication is Journal of Molecular Catalysis A: Chemical (2016), 100-106, database is CAplus.

Five types of non-heme iron complexes, coordinated with imidazole, pyrazole, triazine and pyridine ligands, which had been previously synthesized, were used in the following studies. Among these complexes, the mer-[FeCl₃(terpy)] complex showed the highest catalytic activity for the oxidative degradation of 2,4,6-tribromophenol (TrBP) using KHSO₅ as an oxygen donor. The turnover numbers for the degradation and debromination of TrBP in the mer-[FeCl₃(terpy)]/KHSO₅ catalytic system were estimated to be 1890 ± 1 and 4020 ± 216, resp. The catalytic activity was significantly inhibited at pH 4-7 in the presence of a humic acid, a major component of landfill leachates. However, the percent of TrBP degradation and debromination increased at pH 8. GC/MS analyses showed that a major oxidation product was 2,6-dibromo-p-benzoquinone (DBQ) and its level decreased with increasing reaction time, suggesting that organic acids (identified by LC/TOF-MS) are formed via the ring-cleavage of DBQ. Mineralization to CO₂ was observed to be 15% as a result of the oxidation for a 3 h period, where TOC values before and after the reaction were measured. Absorption spectra of mer-[FeCl₃(terpy)] with m-chloroperoxybenzoic acids as an oxygen donor in acetonitrile showed that a center metal, Fe, formed a peroxide complex with the oxygen donor.

Journal of Molecular Catalysis A: Chemical published new progress about 930-36-9. 930-36-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole, name is 1-Methylpyrazole, and the molecular formula is C4H6N2, Recommanded Product: 1-Methylpyrazole.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Liu, Deng-Feng published the artcileRing-opening copolymerization of epoxide and dianhydride in the presence of manganese(III) asymmetrical bis-Schiff base catalysts, Related Products of pyrazoles-derivatives, the publication is Canadian Journal of Chemistry (2014), 92(11), 1098-1105, database is CAplus.

Based on a series of asym. bis-Schiff base H₂Lⁿ (n = 1-4) ligands with different electronic and steric effects, a series of [Mn(Lⁿ)Cl] complexes 1-4 are obtained and shown to be effective catalysts in ring-opening copolymerization of epoxides and dianhydrides. Through the structure design, the input of electron-withdrawing bromine substituent para to the phenoxide group of the complexes is considerately beneficial to the improved activities. Moreover, steric and electronic effects of the suitable MeO substituent at the ortho orientation on the phenoxide group may both play a role in the formation of alternating ring-opening copolymers under the identical reaction conditions. In three cocatalysts tested, n-Bu₄NBr is pos. to monomer conversion and chain growth of polymer.

Canadian Journal of Chemistry published new progress about 4551-69-3. 4551-69-3 belongs to pyrazoles-derivatives, auxiliary class Benzenes, name is 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and the molecular formula is C17H14N2O2, Related Products of pyrazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Liu, Deng-Feng published the artcileRing-opening copolymerization of epoxides and anhydrides using manganese(III) asymmetrical Schiff base complexes as catalysts, Formula: C17H14N2O2, the publication is RSC Advances (2015), 5(5), 3854-3859, database is CAplus.

Based on a series of asym. Schiff base H₂Lⁿ (n = 1-4) ligands with different electronic and steric effects, a series of [Mn(Lⁿ)Cl] complexes were obtained and shown to be effective catalysts in cyclohexene oxide and maleic anhydride, cyclohexene oxide and phthalic anhydride, styrene oxide and maleic anhydride or styrene oxide and phthalic anhydride ring-opening copolymerizations Through the structure design, the input of the electron-withdrawing Br substituent para to the phenoxide group of the complexes is quite beneficial to the improved activities. Moreover, both steric and electronic effects of a suitable MeO substituent at the ortho position of the phenoxide group have much more influence on the formation of alternating ring-opening copolymers than that of selected reaction conditions.

RSC Advances published new progress about 4551-69-3. 4551-69-3 belongs to pyrazoles-derivatives, auxiliary class Benzenes, name is 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and the molecular formula is C17H14N2O2, Formula: C17H14N2O2.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Song, Zongqiang published the artcileSynthesis of 1,3-Dioxepine-Fused (Tricyclic) Bispyrazoles Involved with Pyrazolone Derivatives and Dichloromethane, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is Journal of Organic Chemistry (2022), 87(6), 4284-4290, database is CAplus and MEDLINE.

A simple and novel method was described for the synthesis of novel 1,3-dioxepine-fused (tricyclic) bispyrazoles I (R = H, Me, t-Bu, Cl, etc.; R¹ = H; RR¹ = -CH=CH-CH=CH-; R² = Me, CF₃, i-Pr, Ph; R³ = H, Me). It involves a Cs₂CO₃ mediated O-alkylation of readily available pyrazolone derivatives II with dichloromethane as methylene source followed by PhI(OAc)₂-mediated intramol. oxidative biheteroaryl coupling under mild conditions. This scalable protocol was applied for the preparation of valuable and novel 1,3-dioxepine-fused (tricyclic) bispyrazoles I which could find potential applications in medicinal or material chem.

Journal of Organic Chemistry published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H19NO3, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics