Category: 27412-71-1

Zimmermann, Diane published the artcileUnambiguous synthesis of 1-methyl-3-hydroxypyrazoles, Quality Control of 27412-71-1, the main research area is pyrazolol methyl preparation.

2,3-Dihydropyrazolo[3,2-b]oxazoles were used as intermediates in a new method for preparation of 1-methyl-3-hydroxypyrazoles. Synthesis of this bicyclic system was achieved either by alkylation of 3-hydroxypyrazole with 1,2-dibromoethane or, with better yields, by cyclization of 1-tosyl-2-(2-hydroxyethyl)pyrazol-3-ones via a nitrogen to oxygen transfer of the tosyl group. Alkylation with Me trifluoromethanesulfonate followed by dihydrooxazole ring-opening with sodium iodide led to the 1-methyl-2-(2-iodoethyl)pyrazoles. Removal of the iodoethyl chain on N-2 to give the target 3-hydroxypyrazoles was achieved either via a cyanation and then a decyanoethylation reaction or via an elimination of hydrogen iodide, followed by an iodine-based oxidation of the resulting vinylic derivative Using the latter method, 1-methyl-3-hydroxypyrazoles were obtained in 58-73% yields from the corresponding 2,3-dihydropyrazolo[3,2-b]oxazoles.

Tetrahedron published new progress about pyrazolol methyl preparation. 27412-71-1 belongs to class pyrazoles-derivatives, name is 5-Phenyl-1H-pyrazol-3(2H)-one, and the molecular formula is C9H8N2O, Quality Control of 27412-71-1.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Baddar, F. G. published the artcilePhenylpropiolic acids. IX. Reaction of arylpropiolic acids with hydrazine and phenylhydrazine, Computed Properties of 27412-71-1, the main research area is phenyl propiolic acid hydrazines; propiolic acid phenyl hydrazines; acid phenyl propiolic hydrazines; hydrazines phenyl propiolic acid; pyrazolones; azines aromatic.

Phenyl-, p-chlorophenyl-, and 3,4-methylenedioxyphenylpropiolic acids react with N2H4 to give, in each case, a mixture of the corresponding pyrazol-5-one and azine. p-Methoxyphenyl- and 3,4-dimethoxy-phenylpropiolic acids give azines only. Phenyl-, p-chlorophenyl-, and m-chlorophenylpropiolic acids react with PhNHNH2 to give the corresponding 5-aryl-1-phenylpyrazol-3-ones.

Journal of the Chemical Society [Section] C: Organic published new progress about phenyl propiolic acid hydrazines; propiolic acid phenyl hydrazines; acid phenyl propiolic hydrazines; hydrazines phenyl propiolic acid; pyrazolones; azines aromatic. 27412-71-1 belongs to class pyrazoles-derivatives, name is 5-Phenyl-1H-pyrazol-3(2H)-one, and the molecular formula is C9H8N2O, Computed Properties of 27412-71-1.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Tawil, Bassem F. published the artcileSynthesis of the spermidine alkaloid (±)-N(1)-acetyl-N(1)-deoxymayfoline, SDS of cas: 27412-71-1, the main research area is deoxymayfoline acetyl synthesis; mayfoline acetyldeoxy synthesis.

The total synthesis of the spermidine alkaloid (±)-N(1)-acetyl-N(1)-deoxymayfoline [(±)-I, R = Ac] was achieved by expansion of rings. The 5-membered cyclic compound II was fused with butadiene by intermol. Diels-Alder cycloaddition The resulting 7-phenyl-1,6-diazabicyclo[4.3.0]nona-3,7-dien-9-one was reductively cleaved with Raney-Ni in alc. KOH to afford the mono-cyclic lactam III (R1 = H). This was selectively alkylated in high yields to the cyano derivative III (R1 = CH2CH2CN). Reduction of the nitrile group to the amine derivative went smoothly by use of Adam’s catalyst in the presence of acid. Intramol. transamidation was then accomplished by acid catalysis to furnish the 13-membered diazalactam I (R = H). The synthesis of (±)-I (R = Ac) was completed by the selective acetylation of the more nucleophilic amino group.

Tetrahedron published new progress about deoxymayfoline acetyl synthesis; mayfoline acetyldeoxy synthesis. 27412-71-1 belongs to class pyrazoles-derivatives, name is 5-Phenyl-1H-pyrazol-3(2H)-one, and the molecular formula is C9H8N2O, SDS of cas: 27412-71-1.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Katritzky, Alan R. published the artcileNovel chromophoric heterocycles based on maleimide and naphthoquinone, Quality Control of 27412-71-1, the main research area is heterocyclic dye pigment; halomaleimide condensation nucleophile; chloronaphthoquinone condensation nucleophile.

1-Phenyl-3,4-dichloromaleimide, 1-propyl-3-bromomaleimide, and 2,3-dichloro-1,4-naphthoquinone were condensed with nucleophiles such as pyrazole, 4-pyridone, imidazole, PhNHNH2, o-H2NC6H4OH, o-H2NC6H4SH, 1,2,4-triazole, benzotriazole, pyridine, etc., to yield a range of heterocyclic dyes and pigments, the visible absorption spectra of which were discussed.

Journal of Heterocyclic Chemistry published new progress about Dyes. 27412-71-1 belongs to class pyrazoles-derivatives, name is 5-Phenyl-1H-pyrazol-3(2H)-one, and the molecular formula is C9H8N2O, Quality Control of 27412-71-1.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Veibel, Stig published the artcilePyrazole studies. VI. Variation of the basic properties of pyrazolones with substitution in the pyrazolone nucleus, Name: 5-Phenyl-1H-pyrazol-3(2H)-one, the main research area is .

cf. C.A. 48, 674g. pKB values were determined for a number of pyrazolones by titration with HClO4 in glacial HOAc. The compounds studied (R’s shown only when other than H), pKB, and m. ps. were: (I), 11.5, 165°; (II), R3 = Me, 10.9, 216-18°; (III), R3 = Me3C, 11.1, 200°; (IV), R3 = Me, R4 = Et, 11.1, 227-8°; (V), R3 = Me, R4 = C3H7, 11.2, 207-8°; (VI), R3 = Me, R4 = C3H5, 11.2, 195-6°; (VII), R3 = Me, R4 = Ph, 11.4, 208-10°; (VIII), R3 = Ph, 11.4, 232-3°; (IX), R1 = R3 = Me, 10.3, 117° (b19 130°); (X), R1 = R3 = Me, R4 = Et, 10.5, 94-5° (from EtOAc) (b15 137°); (XI), R1 = R3 = Me, R4 = C3H7, 10.5, 84-5° (from EtOAc) (b15 150°); (XII), R1 = R3 = Me, R4 = C3H5, 10.5, 71-2°; (XIII), R1 = R3 = Me, R4 = Ph, 10.9, 175° (from aqueous MeOH); (XIV), R1 = Me, R3 = Ph, 10.9, 206°; (XV), R1 = Ph, R3 = Me, 11.3, 127°; (XVI), R1 = Ph, R3 = Me, R4 = Et, 11.5, 111°; (XVII), R1 = Ph, R3 = Me, R4 = Pr, 11.4, 101-2° (XVIII), R1 = R4 = Ph, R3 = Me, 11.9, 199-200°; (XIX), R1 = R3 = Ph, 12.2, 137°; (XXa), R1 = Ph, R3 = Me, R4 = Cl, 13.2, 153°; (XXb), R1 = Ph, R3 = Me, R4 = Br, 13.3, 122°; (XXI), R1 = Ph, R2 = R3 = Me, 11.2, 113°; (XXII), R1 = Ph, R2 = R3 = Me, R4 = Me2CH, 11.6, 101-3°; (XXIII), R1 = Ph, R3 = Me, R4 = pyrazolonyl, 13.0, decompose; (XXIV), R1 = Ph, R3 = Me, R4 = 3-methyl-5-oxo-1-phenyl-2-oxazolidin-4-ylidenemethyl, 13.8, 185°; (XXV), R1 = Ph, R3 = Me, R4 = PhCH:CPh, 12.2, 220°; (XXVI), R3 = Me, R2 = R4 = Et, > 15, 104-5°; (XXVII), R1 = Ph, R2 = R3 = Me, R4 = Cl, > 15, 68°; (XXVIII), R1 = Ph, R2 = R4 = Et, R3 = Me, > 15, 161-2°; (XXIX), R1 = Ph, R4 = Me, 12.2, 167°; (XXX), R1 = Ph, R3 = Et, R4 = Me, 12.3, 172°; (XXXI), R1 = R4 = Ph, 12.9, 256°; (XXXII), R1 = Ph, R2 = R4 = Me, 11.6, 113°; and (XXXIII), R1 = Ph, R2 = OMe (at C3), R4 = Me, 12.5, b16 154-6°. Me3CCOCH2CO2Et (7.5 g.), 10 cc. EtOH and 4 cc. 60% N2H4.H2O allowed to stand 2-3 hrs. and filtered gave 4.2 g. III, recrystallized from aqueous EtOH. VII was similarly prepared in 27% yield from AcCHPhCO2Et (XXXIV). In the preparation of IX to XIV, a suspension of 1 mole Ba(OH)2.8H2O in 500 cc. H2O was heated at 100°, 1 mole N2H4.H2SO4 in 150 cc. H2O at 70° added, then 300 cc. H2O, the mixture stirred 1 hr. at 70% filtered, the BaSO4 washed with hot H2O, the combined filtrate and washings made up to 1 l. with H2O; heated with 0.2 mole α-substituted Et acetoacetate or Et benzoylacetate and 200 cc. N MeNHNH2 at 70° for various times, the solution extracted twice with ligroine, the H2O removed at 45-50° in vacuo from the aqueous layer, the residue taken up in CHCl3, dried with anhydrous Na2SO4, the CHCl3 evaporated, and the crude pyrazolone purified. The yields of IX to XIV were 51, 60, 65, 50, 70, and 65%, resp., and the reaction time 0.5, 10, 10, 5, 10, and 10 hrs. XXXIV (4 g.) and 2 g. PhNHNH2 heated 1 hr. at 140° gave 3.2 g. XVIII. XXV was prepared in 50% yield by heating equimolar amounts of 1-phenyl-3-methylpyrazolin-5-one 3-4 hrs. with PhCH2Bz, filtering, washing the product with Et2O, and recrystallizing from glacial HOAc. The dipole moments of XXXII and XXXIII were determined

Acta Chemica Scandinavica published new progress about Basicity. 27412-71-1 belongs to class pyrazoles-derivatives, name is 5-Phenyl-1H-pyrazol-3(2H)-one, and the molecular formula is C9H8N2O, Name: 5-Phenyl-1H-pyrazol-3(2H)-one.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Moriarty, R. M. published the artcileHypervalent iodine oxidation of 5-substituted and 4,5-disubstituted pyrazol-3(2H)-ones. A facile synthesis of methyl-2-alkynoates and methyl 2,3-alkadienoates, Application of 5-Phenyl-1H-pyrazol-3(2H)-one, the main research area is pyrazolone oxidation iodine hypervalent; alkynoate methyl; alkadienoate methyl.

Hypervalent iodine oxidation of various 5-substituted pyrazol-3(2H)-ones I (R = Me, Et, CO2Me, CH2CO2Me, Ph, 4-ClC4H4, 4-MeC6H4, 4-MeOC6H4) with iodobenzene diacetate or iodosobenzene in methanol results in fragmentative loss of mol. dinitrogen to yield RCCCO2Me. However, 5-methyl-4-substituted pyrazol-3(2H)-ones II (R1 = Me, Et, CH2CO2Me, CH2Ph) under similar conditions yield Me 2,3-allenic esters H2C:C:CRCO2Me. Me 2,3-cycloalkadienoates III (n = 6, 7, 9) are obtained by the oxidative cleavage of 4,5-polymethylene pyrazol-3(2H)-ones IV using iodobenzene diacetate or iodosobenzene in methanol. The scope and mechanism of these reactions are discussed.

Tetrahedron published new progress about Oxidation. 27412-71-1 belongs to class pyrazoles-derivatives, name is 5-Phenyl-1H-pyrazol-3(2H)-one, and the molecular formula is C9H8N2O, Application of 5-Phenyl-1H-pyrazol-3(2H)-one.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Guillou, Sandrine published the artcile5-Iodo-3-ethoxypyrazoles: an entry point to new chemical entities, Application In Synthesis of 27412-71-1, the main research area is substituted pyrazole preparation; arylation; heterocycles; organic synthesis; palladium; pyrazoles.

Our program, which has focused on the preparation of new pyrazole derivatives, has led us to report here an original and simplified preparation of Et 3-ethoxy-1H-pyrazole-4-carboxylate. This is based on the reaction of hydrazine monohydrochloride and di-Et 2-(ethoxymethylene)malonate. Further transformations of this key compound allowed the preparation of the two possible iodinated isomers, namely, 3-ethoxy-4-iodo- and 3-ethoxy-5-iodo-1H-pyrazole. These compounds have opened the way to a quick access to many original pyrazole series. As an illustration, we report here on the selectivity of N-arylation, by using the Lam and Cham method, the C4- and C5-arylation of some of these 3-ethoxypyrazole derivatives by using the Suzuki-Miyaura reaction, and C5-benzylation reactions by means of the Negishi reaction. This was followed by hydrolysis of the ethoxy group, which led to the corresponding pyrazol-3-one derivatives As a conclusion of this work, we conducted an investigation into the regiochem. of the condensation between di-Et 2-(ethoxymethylene)malonate and the hydrochloride salts of Me, benzyl, or Ph hydrazine.

Chemistry – A European Journal published new progress about Arylation. 27412-71-1 belongs to class pyrazoles-derivatives, name is 5-Phenyl-1H-pyrazol-3(2H)-one, and the molecular formula is C9H8N2O, Application In Synthesis of 27412-71-1.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Evans, N. A. published the artcileTautomerism in the 5-pyrazolone series. 1(H)-5-Pyrazolones and indazolones, Application of 5-Phenyl-1H-pyrazol-3(2H)-one, the main research area is .

Preparation according to Wolff (W. and Schreiner, CA 2, 1451) gave the tautomer MeC(:NNHCMe:CHCO2Et)CH2CO2Et (I), m. 46°; the ester (II), m.. 188°; the lactone (III, R = H) (IV), m. 250°; and III (R = Ac) (V), m. 184°. AcCH2CO2Et(0.01 mol) and 0.01 mol H2NNHAc refluxed 3 h. in alc. gave 55% MeC(:NNHAc)CH2CO2Et (VI), m. 82°. The assigned structure for I was deduced from the N.M.R. spectrum. I was recovered unchanged from C5H5N. I readily rearranged to II and its structure was unambiguously formulated on the basis of the N.M.R. and ir data. The formulation for III followed from the N.M.R. spectrum. IV showed a broad band at νNH 3225 cm.-1 (KCl) removed by acetylation to give V, νCO 1739 cm.-1 (KCl). Spectral data in solution and solid state were consistent with the formulation of II in the enolic form of the pyrazoline ring and suggested that other simpler 1(H)-5-pyrazolones might be formulated better as the enol rather than as the lactam. It was shown that II, 1(H)-3-methyl-5-pyrazolone (VII) (R = R2, R3 = H, R1, = Me) (VIII), m. 217°, VII (R = R2 = R3 = H, R1 = Ph) (IX), m. 236°, and related compounds exist in the enolic form in the solid state and predominantly so in solvents in which they are soluble VIII (3 g.) in 10 mL. C5H5N heated on a steam bath and stirred with dropwise addition of 3.1 g. AC2O, the solution heated 10 min. and diluted with H2O yielded 70% N-Ac derivative, m. 170-2°. VIII (1 g.) heated 1 h. on a steam bath in 5 mL. Ac2O and the product sublimed gave 80% yield of the diacetate (VII, R = R3 = Ac, R1 = Me, R2 = H), m. 38°. Spectral data obtained for VII (R = R3 = Bz, R1 = Me, R2 = H), m. 128°, supported the earlier formulations as 1-benzoyl-3-methyl-5-benzoyloxypyrazole. The isomeric acetates of IX were prepared according to the literature and the structures differentiated by the ir data confirmed the formulations previously proposed by Weissberger and Porter (CA 38, 972). Indazolone derivatives (X) were found to be represented exclusively by the enolized structure. Indazolone (X, R = R’ = H) (XI, 0.19 g.) and 0.2 g. p-MeC6H4SO2Cl refluxed 30 min. in 8 mL. C5H5N gave 0.17 g. X (R = H, R’ = p-MeC6H4SO2) (XII), m. 147°. XII refluxed 2 h. in Ac2O and the mixture kept 16 h. at 19° gave X (R = Ac, R’ = p-MeC6H4SO2) (XIII), m. 106°. C5H5N (10 mL.) containing 1 g. o-H2NNHC6H4CO2H and 1 g. p-MeC6H4SO2Cl refluxed 30 min. gave 0.73 g. α-(ο-carboxyphenyl)-β-tolylsulfonylhydrazine, m. 187° (decomposition), heated (0.17 g.) 2 h. in 6 mL. on a water bath to give 0.15 g. 1-acetyl-2-tolylsulfonylindazolone (XIV). The difference in the uv spectra between XII and XIII on the one hand and between XII and XIV on the other was a confirmation of the ir and chem. basis for determining their structures. XI methylated with 3-fold excess of CH2N2 in Et2O-MeOH at 0° 2 h. gave X (R = H, R’ = Me), m. 104°; Ac derivative m. 89° (petr. ether). The high frequencies found for CO groups in the ir spectra reflect a lack of conjugation with the π-electrons of the heterocyclic ring. The progressive movement to higher frequencies observed in the solution spectra of the 1-acetylspectra of the 1-acetylindazolones as the 3-substituent increases in electron withdrawing power (OMe < OAc < O3SC6H4Me-p) suggests that the N lone pair contributes to the π-electron system and that the acyl CO group reflecting the diminished conjugation approximates more to the state of a Me ketone modified by the direction bond to an atom of greater electronegativity. Tetrahedron published new progress about IR spectra. 27412-71-1 belongs to class pyrazoles-derivatives, name is 5-Phenyl-1H-pyrazol-3(2H)-one, and the molecular formula is C9H8N2O, Application of 5-Phenyl-1H-pyrazol-3(2H)-one.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Omar, Mohamed T. published the artcileA new synthetic route to 3-oxo-5-phenyl-2,3-dihydropyrazoles, Safety of 5-Phenyl-1H-pyrazol-3(2H)-one, the main research area is pyrazolone phenyl; phenylpyrazolone; hydrazine benzylidenethiazolidinedione rearrangement.

The reaction of RNHNH2 (R = H, Me) with benzylidenethiazolidinediones I (R1 = PhCH2, Et, allyl) gave the resp. pyrazolones II. I (R1 = PhCH2) was heated with PhNHNH2 in EtOH to give II (R = Ph) and addition product III; a mixture of III, pyridine, Et3N, and EtOH was refluxed 4 h to give II (R = Ph).

Synthesis published new progress about Rearrangement. 27412-71-1 belongs to class pyrazoles-derivatives, name is 5-Phenyl-1H-pyrazol-3(2H)-one, and the molecular formula is C9H8N2O, Safety of 5-Phenyl-1H-pyrazol-3(2H)-one.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Al-Mutairi, Aamal A. published the artcileMicrowave versus ultrasound assisted synthesis of some new heterocycles based on pyrazolone moiety, Synthetic Route of 27412-71-1, the main research area is pyrazolone derivative preparation microwave ultrasound comparison.

Different pyrazolone derivatives were prepared by microwave irradiation and ultrasound assisted methods besides the traditional ones. They were used for synthesis of some derivatives of spiropiperidine-4,4′-pyrano[2,3-c]pyrazole, dihydropyrano[2,3-c]pyrazole, pyrazole-4-carbothioamide, 4-(2-oxo-1,2-diphenylethylidene)-1H-pyrazol-5(4H)-one, azopyrazole, arylmethylenebis-1H-pyrazol-5-ol and arylidene-1H-pyrazol-5(4H)-one via reactions with different reagents applying the ultrasound method in some cases.

Journal of Saudi Chemical Society published new progress about Green chemistry. 27412-71-1 belongs to class pyrazoles-derivatives, name is 5-Phenyl-1H-pyrazol-3(2H)-one, and the molecular formula is C9H8N2O, Synthetic Route of 27412-71-1.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics