Category: 14580-22-4

Feng, Kai-Xiang published the artcileEnantioselective Syntheses of C₂-Symmetric Pyrazolones and Diones via One-Pot Organo-/Iodine Sequential Catalysis, Synthetic Route of 14580-22-4, the publication is Organic Letters (2021), 23(17), 6750-6755, database is CAplus and MEDLINE.

The catalytic diastereo- and enantioselective synthesis of C₂-sym. axially chiral 1,4-dicarbonyl derivatives with 2,3-quaternary stereocenters I (R = 3-bromophenyl, 2-methylphenyl, 3-chlorophenyl; R¹ = n-Pr, Ph, naphthalen-1-yl, thiophen-2-yl, etc.; R² = Et, Pr, i-Pr, cyclopropyl), II (R = i-Pr, 2-fluorophenyl, 2-nitrophenyl, etc.; R² = Ph, 4-fluorophenyl, 4-bromophenyl, etc.; R³ = Ph, naphthalen-2-yl, furan-2-yl, etc.) and III was achieved by utilizing an organo-/iodine binary catalytic strategy. The reactions proceeded well under mild conditions without metals or strong bases.

Organic Letters 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, Synthetic Route of 14580-22-4.

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

Asghar, Soneela published the artcileCobalt-Catalyzed Suzuki Biaryl Coupling of Aryl Halides, Synthetic Route of 14580-22-4, the publication is Angewandte Chemie, International Edition (2017), 56(51), 16367-16370, database is CAplus and MEDLINE.

Readily accessed cobalt pre-catalysts with N-heterocyclic carbene ligands catalyze the Suzuki cross-coupling of aryl chlorides and bromides with alkyllithium-activated arylboronic pinacolate esters. Preliminary mechanistic studies indicate that the cobalt species is reduced to Co⁰ during the reaction.

Angewandte Chemie, International Edition 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, Synthetic Route of 14580-22-4.

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

Yang, Xiaoqun published the artcileAsymmetric Synthesis of Structurally Sophisticated Spirocyclic Pyrano[2,3-c]pyrazole Derivatives Bearing a Chiral Quaternary Carbon Center, Name: 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is Organic Letters (2022), 24(29), 5474-5479, database is CAplus and MEDLINE.

A carbene-catalyzed enantio- and diastereoselective [2 + 4] cycloaddition reaction is developed for quick and efficient access to structurally complex multicyclic pyrano[2,3-c]pyrazole mols. I (R = Me, Ph, 1-naphthyl, etc.; R¹ = H, Me, F; R² = H, Br, F; R³ = H, Me; R⁴ = Me, Bn, Ac, H; R⁵ = Me, Ph, 2-chlorophenyl). The reaction tolerates a broad scope of substrates bearing various substitution patterns, with the multicyclic pyrano[2,3-c]pyrazole products I afforded in generally good to excellent yields and optical purities. The chiral mols. obtained from this approach have found promising applications in the development of novel bactericides for plant protection.

Organic Letters 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 C5H8N2O, Name: 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.

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

Toonchue, Saowanee published the artcileMetal-free direct oxidative C-C bond coupling of pyrazolones and quinoxalinones, Product Details of C10H9ClN2O, the publication is Organic Chemistry Frontiers (2018), 5(12), 1928-1932, database is CAplus.

A highly efficient transition metal-free oxidative chemo- and regioselective C-C bond coupling of pyrazolones and quinoxalinones mediated by K₂S₂O₈ was described. This reaction was conveniently carried out under mild conditions which gave various hydroxy-pyrazolyl quinoxalinone products in moderate to excellent yields in a short reaction time.

Organic Chemistry Frontiers 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 C5H5NO3S, Product Details of C10H9ClN2O.

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

Padmaja, Pannala published the artcileSynthesis, molecular docking and in vitro antiproliferative activity of novel pyrano[3,2-c]carbazole derivatives, Recommanded Product: 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is New Journal of Chemistry (2016), 40(10), 8305-8315, database is CAplus.

A new series of polycyclic pyrano[3,2-c]carbazole derivatives have been synthesized by domino Knoevenagel-hetero-Diels-Alder reactions. The key strategy involves ethylenediamine diacetate (EDDA) catalyzed cyclization of the O-prenyl derivative of N-Boc-carbazole-3-carboxaldehyde with cyclic 1,3-diketones or pyrazol-5-ones to afford cis-fused N-Boc-pyrano[3,2-c]carbazole derivatives The reactions were clean and highly diastereoselective, affording the desired products in good yields. The deprotection of the Boc group under acidic conditions led to pyrano[3,2-c]carbazole derivatives The antiproliferative activity of all the synthesized compounds on three cancer cell lines such as PANC 1 (pancreatic), HeLa (cervical) and MDA-MB-231 (breast cancer) was investigated. Three compounds including I displayed pronounced antiproliferative activity. The antimicrobial activity of these compounds was assayed against three representative Gram-pos. organisms and Gram-neg. organisms. Compound I exhibited significant antimicrobial activity. Mol. docking studies revealed that the lead compounds selectively occupy the colchicine binding site of tubulin.

New Journal of 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, Recommanded Product: 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.

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

Chattaway, F. D. published the artcileHalogen-substituted 1-arylpyrazolones, Related Products of pyrazoles-derivatives, the publication is Journal of the Chemical Society, Transactions (1924), 2423-7, database is CAplus.

The 1-chlorophenyl-3-methyl-5-pyrazolones are very similar in properties to the unsubstituted base, neither the position of the substituted halogen nor its accumulation in the Ph residue appearing greatly to affect the reactivity of the CH₂ group. 1-o-Chlorophenyl-3-methyl-5-pyrazoline (I), m. 199°, results by heating MeC(:NNHC₆H₄Cl)CH₂CO₂Et at 150-70° for about 90 mins.; HCl salt, m. 154°, decomposes 172°; 4-oximino derivative, golden brown, m. 174°; 4-benzylidene derivative, orange, m. 159°; 4-azo-o-chlorobenzene derivative, golden yellow, m. 212°. I, heated with MeI in MeOH in a sealed tube at 100-20° for 10 hrs., gives the 2,3-di-Me derivative (o-chloroantipyrine), m. 113°, whose aqueous solution has a strong bitter taste. 1-m-Chloro derivative (II), m. 131°; HCl salt, m. 184° (decomposition); 4-oximino derivative, orange, m. 173° (decomposition); 4-benzylidene derivative, red, m. 128°; 4-azo-2′,4′-dichlorobenzene, golden brown, m. 190°; II, heated with Me₂CO 4 hrs., gives the 4-isopropylidene derivative, S-yellow, m. 110°; 2,3-di-Me derivative (m-chloroantipyrine), m. 89-90°; its aqueous solution has an extremely bitter taste. II, heated with PhNHNH₂ until NH₃ is no longer liberated, and NaNO₂ in NaOH, added to an excess of dilute H₂SO₄, give m-chloropyrazole-blue, C₂₀H₁₄O₂N₄Cl₂, dark blue, m. 209° (decomposition); this also results by boiling II with FeCl₃; the other Cl derivatives do not show this reaction. It is easily reduced to the bispyrazolone. 1-p-Chloro HCl salt, m. 194-5° (decomposition); 4-oximino derivative, orange needles, m. 180° (decomposition); it also exists as the unstable form, brick-red, compact triclinic prisms; 4-benzylidene derivative, scarlet, m. 156°; 4-azo-p-chlorobenzene, orange-red, m. 232°; 2, 3-di-Me derivative (p-chloroantipyrine), m. 126°; this also has a very bitter taste. Bis-1-chlorophenyl-3-methyl-5-pyrazolone, decomposes without melting; p-chloropyrazole-blue, blue, decomposed at about 300°. 1,2,4-Dichlorophenyl-3-methyl-5-pyrazolone, m. 178°; HCl salt, m. 153°, decomposes 170°; 4-oximino derivative, canary-yellow, m. 166-8° (decomposition); 4-benzylidene derivative, orange, m. 131°; 4-azobenzene derivative, orange, m. 137-8°; 2, 3-di-Me derivative, m. 143°; the aqueous solution has a bitter taste.

Journal of the Chemical Society, Transactions 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, Related Products of pyrazoles-derivatives.

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

Guise, G. B. published the artcileNew approaches to washfast dyes for wool. II. Synthesis and dyeing properties of model isothiouronium dyes, Product Details of C10H9ClN2O, the publication is Journal of the Society of Dyers and Colourists (1975), 91(8), 259-64, database is CAplus.

Nine dyes with the CH2CH2SC(NH2):NH2+X- group (X = Br, iodine) were prepared and gave fast dyeings on wool in cationic form and on polyesters in disperse form (by decomposition to the thiol immediately before application). P-C6H4(NH2)2 [106-50-3] was acylated with BrCH2CH2COCl [15486-96-1], and the resulting 4-BrCH2CH2CONHC6H4NH2.HCl [57058-91-0] was diazotized and coupled with 1-(2-chlorophenyl)-3-methyl-5-pyrazolone [14580-22-4] to give an azopyrazolone, which was treated with (H2N)2CS to give I [57058-92-1]. The 8 other azo and anthraquinone dyes were prepared as described in Ger. Offen. 1,962,859 (1970). Level dyeings on wool-polyester blends could be obtained by decomposing the dye to the disperse form in an alk. bath, neutralizing, and adding more dye to give a mixture of the cationic and disperse forms. The cationic dyes also readily dyed silk, hair, and acrylic fibers, but their fastness on cellulosics was inadequate. It seems unlikely that the fastness on wool is due to formation of mixed disulfides with cystine units.

Journal of the Society of Dyers and Colourists 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, Product Details of C10H9ClN2O.

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

Wrzeciono, U. published the artcileAzoles. Part 2: furyl and 5-nitrofuryl derivatives of 1-chlorophenyl-3-methylpyrazolones(5), Computed Properties of 14580-22-4, the publication is Pharmazie (1978), 33(5), 264-6, database is CAplus and MEDLINE.

Condensation of the furfurals I (R = H, Me) with the pyrazolones II (R¹ = 2-, 3-, 4-Cl) gave III (R, R¹ as above, R²R³ = bond), which were readily reduced by NaBH₄ to III (R² = R³ = H), having bactericidal activity against Staphylococcus aureus at 39-1250 mg/mL.

Pharmazie 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 C7H16ClNO2, Computed Properties of 14580-22-4.

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

Parmar, Narsidas J. published the artcileCatalyst-and solvent-free one-pot synthesis of some novel polyheterocycles from aryldiazenyl salicylaldehyde derivatives, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is RSC Advances (2012), 2(7), 3069-3075, database is CAplus.

A catalyst- and solvent-free domino/Knoevenagel-hetero-Diels-Alder (DKHDA) reaction of allyl/prenyl ether-tethered aryldiazenylsalicylaldehydes with corresponding pyrazolones and heterocyclic 1,3-diketones is described. Subsequent reduction of aryldiazenylpolyheterocycles, thus obtained in high yields (70-86%), afforded amino frameworks with anticipated biol. activity. While in a conventional procedure, no reaction was observed without activation of an allyl-based substrate, an excellent yield was achieved at higher temperature For a prenyl based substrate, however it underwent smoothly to form a desired cyclized product. The stereochem. of the compound was confirmed by various NMR experiments and a single crystal X-ray diffraction anal.

RSC Advances 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

Parmar, Narsidas J. published the artcileAn efficient domino reaction in ionic liquid: Synthesis and biological evaluation of some pyrano- and thiopyrano-fused heterocycles, COA of Formula: C10H9ClN2O, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(6), 1656-1661, database is CAplus and MEDLINE.

An improved domino/Knoevenagel-hetero-Diels-Alder reaction of two new aldehyde substrates; 7-olefinoxy-coumarin-8-carbaldehyde and 2-alkensulfanyl-quinoline-3-carbaldehyde, with pyrazolones was studied in the ionic liquid triethylammonium acetate (TEAA), affording a series of pyrazolopyran annulated-pyrano-fused coumarins, and thiopyrano-fused quinolones. Besides acting as the catalyst, since no addnl. catalyst used, the ionic liquid TEAA also provided an easy recovery. In the polyheterocycles prepared, the cis-fusion of the two pyranyl rings has been inferred from 2D NMR COSY and NOESY experiments All are good antitubercular agents, as they are found active against Mycobacterium tuberculosis H37Rv, and antibacterial agents, as they are found active against three Gram-pos. (Streptococcus pneumoniae, Clostridium tetani, Bacillus subtilis) and three Gram-neg. (Salmonella typhi, Vibrio cholerae, Escherichia coli) bacteria.

Bioorganic & Medicinal Chemistry Letters 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, COA of Formula: C10H9ClN2O.

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