Tag: M.W=200-250

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

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

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

Malik, G. M. published the artcileSynthesis, characterization and dyeing properties of mono azo pyrazolone dyes based on 2-amino 5-methyl thiazole, Formula: C10H9ClN2O, the publication is International Journal of Chemistry (Mumbai, India) (2015), 4(3), 284-294, database is CAplus.

Different substituted monoazo pyrazolone dyes from N⁴-(5-methyl-1,3-thiazol-2-yl)-1,3-thiazole-2,4-diamine have been synthesized. The condensation of 5-Me 2-amino thiazole with chloroacetylchloride yielded 2-chloro-N-(5- methyl-1,3-thiazol-2-yl)acetamide which was reacted with thiourea at reflux temperature using methanol and cyclized to yield N⁴-(5-methyl-1,3-thiazol-2-yl)-1,3-thiazole-2,4-diamine. This was diazotized and coupled with various substituted pyrazolones to give a new series of pyrazolone dyes, which were characterized using elemental anal., UV, IR and 1H NMR spectra. Dyeing performance and fastness properties were evaluated by applying them on nylon and polyester fabrics.

International Journal of Chemistry (Mumbai, India) 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, Formula: C10H9ClN2O.

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

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

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

Li, Shasha published the artcileMerging Late-Stage Diversification with Solid-Phase Peptide Synthesis Enabled by High-Throughput On-Resin Reaction Screening, Safety of 1-(3-Chlorophenyl)pyrazole-4-boronic acid, the publication is ACS Catalysis (2022), 12(5), 3201-3210, database is CAplus.

An integrated workflow is described that combines micromole-scale high-throughput experimentation (HTE) reaction screening and solid-phase peptide synthesis (SPPS) to enable rapid synthetic method development for on-resin peptide diversification. Using this new approach, we have identified several sets of robust Suzuki-Miyaura coupling conditions with complementary scope that collectively display broad coverage with respect to both resin-bound peptide substrates containing aryl halide side chains and (hetero)arylboronic acid coupling partners. We have also demonstrated the utility of this integrated SPPS/chem. diversification method by synthesizing a multidimensional library of diverse peptides in high yields.

ACS Catalysis published new progress about 1072945-88-0. 1072945-88-0 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Chloride,Boronic acid and ester,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is 1-(3-Chlorophenyl)pyrazole-4-boronic acid, and the molecular formula is C9H8BClN2O2, Safety of 1-(3-Chlorophenyl)pyrazole-4-boronic acid.

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

Parmar, Narsidas J. published the artcileSolvent-free, one-pot synthesis and biological evaluation of some new dipyrazolo [3,4-b:4′,3′-e]pyranylquinolones and their precursors, Related Products of pyrazoles-derivatives, the publication is Medicinal Chemistry Research (2014), 23(1), 42-56, database is CAplus.

One-pot synthesis of 24 new compounds, belonging to three families; dipyrazolo[3,4-b:4′,3′-e]pyranylquinolones and its precursors (pyrazolonylidene)methylquinolones and 4,4′-[(quinolinyl)methylene]bispyrazols, has been achieved in the presence of catalyst tetrabutylammonium hydrogen sulfate (TBA-HS) in solvent-free conditions. In addition to assuring chromatog.-free product isolation, this method had also allowed the reaction to proceed in a regio-selective manner provided the temperature and amount of pyrazolone are varied. At 100 °C, while 1:1 mixture of aldehyde 3 and pyrazolone 4 underwent Knoevenagel condensation, same reactants taken in ratio of 1:2 mainly domino/Knoevenagel-Michael reaction. At 120 °C, however, the domino/Knoevenagel-Michael-adducts converted into cyclized product, highlighting a new domino/Knoevenagel-Michael-cyclization synthetic sequence. The structure of all heterocycles has been confirmed by mass, IR and NMR spectral data. Based on 2D NMR NOESY experiment, it was also confirmed that the formation of only Z’ configuration of Knoevenagel alkene took place in the transformation. All are good antitubercular agents as they were found to be active against M. tuberculosis H37RV, in addition to being found active against three Gram-pos. (Streptococcus pneumoniae, Clostridium tetani, Bacillus subtilis) and three Gram-neg. (Salmonella typhi, Vibrio cholerae, Escherichia coli) bacteria, resp.

Medicinal Chemistry Research 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

Parmar, Narsidas J. published the artcileTriethylammonium acetate-mediated domino-Knoevenagel-hetero-Diels-Alder reaction: synthesis of some angular polyheterocycles, Computed Properties of 14580-22-4, the publication is Monatshefte fuer Chemie (2013), 144(6), 865-878, database is CAplus.

A solvent-cum catalyst, ionic liquid triethylammonium acetate-mediated one-pot procedure for the synthesis of some new angular benzopyrano[3,4-c]pyrano-fused pyrazoles, e.g., I, all of which incorporate a tertiary ring junction carbon, has been developed. The stereochem. of the products has been confirmed by single-crystal X-ray diffraction data.

Monatshefte fuer Chemie 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, Computed Properties of 14580-22-4.

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