15366-34-4 | pyrazoles-derivatives

Xu, Di’s team published research in Synlett in 2020 | CAS: 15366-34-4

Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4) belongs to pyrazoles. The application of pyrazole derivatives in the development of anticancer agents has been thoroughly investigated and verified. Moreover, the medicinal features of a number of natural products incorporating pyrazole moiety such as pyrazofurin, pyrazofurin B, pyrazole-3(5)-carboxylic acid and 4-methylpyrazole-3(5)-carboxylic acid have been reported.HPLC of Formula: 15366-34-4

《Magnesium-Catalyzed N2-Regioselective Alkylation of 3-Substituted Pyrazoles》 was published in Synlett in 2020. These research results belong to Xu, Di; Frank, Lena; Nguyen, Tina; Stumpf, Andreas; Russell, David; Angelaud, Remy; Gosselin, Francis. HPLC of Formula: 15366-34-4 The article mentions the following:

A highly regioselective Mg-catalyzed alkylation of 3-substituted pyrazoles, I (R1 = Ph, Br, i-Pr, etc.; R2 = H, Br, CHO) and 2,4-dihydro-[1]benzopyrano[4,3-c]pyrazole has been developed to provide N2-alkylated regioisomers II (R3 = C(O)N(CH3)2, C6H5, [4-(morpholin-4-yl)piperidin-1-yl]carbonyl, etc.) and 2-(1H,4H-chromeno[4,3-c]pyrazol-1-yl)-N,N-dimethylacetamide. Using α-bromoacetates like iso-Pr 2-bromoacetate and acetamides R3CH2Br as alkylating agents, this new method was applied to a variety of 3-substituted and 3,4-disubstituted pyrazoles I to produce the N2-alkylated products II with high regioselectivities ranging from 76:24 to 99:1 and 44-90% yields. In the experimental materials used by the author, we found Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4HPLC of Formula: 15366-34-4)

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

Yang, Tao’s team published research in JACS Au in 2022 | CAS: 15366-34-4

Yang, Tao; Li, Xiaoqian; Deng, Shuang; Qi, Xiaotian; Cong, Hengjiang; Cheng, Hong-Gang; Shi, Liangwei; Zhou, Qianghui; Zhuang, Lin published an article in 2022. The article was titled 《From N-H Nitration to Controllable Aromatic Mononitration and Dinitration-The Discovery of a Versatile and Powerful N-Nitropyrazole Nitrating Reagent》, and you may find the article in JACS Au.Reference of Methyl 1H-pyrazole-3-carboxylate The information in the text is summarized as follows:

Herein,the identification of a powerful nitrating reagent, 5-methyl-1,3-dinitro-1H-pyrazole, from the N-nitro-type reagent library constructed using a practical N-H nitration method was reported. This nitrating reagent behaved as a controllable source of the nitronium ion, enabling mild and scalable nitration of a broad range of (hetero)arenes with good functional group tolerance. Of note, this nitration method was controlled by manipulating the reaction conditions to furnish mononitrated or dinitrated product selectively. The value of this method in medicinal chem. was well established by its efficient late-stage C-H nitration of complex biorelevant mols. D. functional theory (DFT) calculations and preliminary mechanistic studies reveal that the powerfulness and versatility of this nitrating reagent were due to the synergistic “”nitro effect”” and “”methyl effect””.Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Reference of Methyl 1H-pyrazole-3-carboxylate) was used in this study.

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

Shi, Jiale’s team published research in Green Chemistry in 2021 | CAS: 15366-34-4

Shi, Jiale; Yuan, Tao; Wang, Rong; Zheng, Meifang; Wang, Xinchen published their research in Green Chemistry in 2021. The article was titled 《Boron carbonitride photocatalysts for direct decarboxylation: the construction of C(sp3)-N or C(sp3)-C(sp2) bonds with visible light》.COA of Formula: C5H6N2O2 The article contains the following contents:

A metal-free protocol was established for the decarboxylative N-H or C(sp2)-H functionalization of acids via metal-free boron carbon nitride (BCN) photocatalysis, delivering the desired products under ambient conditions. This methodol.was applicable to the late-stage modification of pharmaceutical mols. and gram-scale experiments as well as in the recovery and reuse of the photocatalysts without the loss of reactivity. The developed photochem. reaction system fulfills the requirements of green and sustainable chem. In the experiment, the researchers used Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4COA of Formula: C5H6N2O2)

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

Tanwar, Lalita’s team published research in Organic Letters in 2021 | CAS: 15366-34-4

Tanwar, Lalita; Boergel, Jonas; Lehmann, Johannes; Ritter, Tobias published their research in Organic Letters in 2021. The article was titled 《Selective C-H Iodination of (Hetero)arenes》.SDS of cas: 15366-34-4 The article contains the following contents:

A strategy for selective C-H iodination of (hetero)arenes was decribed with a broad functional group tolerance. The utility and differentiation to other iodination methods of supposed sulfonyl hypoiodites for a set of carboarenes and heteroarenes was described.Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4SDS of cas: 15366-34-4) was used in this study.

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

Graner, R. Franquesa’s team published research in Galenica Acta in 1959 | CAS: 15366-34-4

In 1959,Graner, R. Franquesa published 《Synthesis of 2-acetamido-5-nitrothiazole, an oral bactericide》.Galenica Acta published the findings.Application In Synthesis of Methyl 1H-pyrazole-3-carboxylate The information in the text is summarized as follows:

Tech. 2-aminothiazole-HCl was purified by neutralizing with NaOH at 50°, cooling with the addition of the solid amine to prevent supercooling, washing at pH 11-12, then with a saturated solution of NaCl, and then H2O. The solid was air-dried and distilled, b12 139-43°; 65% 2-aminothiazole (I) was recovered. Preparation of 2-acetamido-5-nitrothiazole (II) (CA 46, 10285h; 40, 40583) was accomplished by acetylation, then nitration of I (78.2% over-all yield), and by the reverse steps (62.8% over-all). Ac2O (1.3 mole), 1 mole I, and 0.1 mole H2SO4 was refluxed 10 min., poured on ice, and the solid recrystallized m. 209-10°, for a 92% yield of 2-acetamidothiazole (III). III (142 g.) was dissolved in 450 ml. concentrated H2SO4 at 10° with the addition of 46 ml. (d. 1.5) fuming HNO3 over 40 min.; allowing the temperature to reach 50° for 30 min., pouring on ice, filtering, and washing with water, EtOH, and recrystallizing from AcOH (50 ml./5 g.) gave 152 g. II, m. 265-6°. I (100 g.) was dissolved in 300 ml. concentrated H2SO4 at 10°, and 46 ml. (d. 1.5) fuming HNO3 was added dropwise with agitation at 12°. The temperature was kept 3 hrs. at 0°, then at 25° for 24 hrs. The mass was poured onto 5000 ml. icewater, and the filtrate neutralized with 600 g. Na2CO3 in 2000 ml. H2O. The product was water-washed, and recrystallized from EtOH (100 ml./5 g.) to give 100 g. 2-amino-5-nitrothiazole (IV), m. 202-3°. IV (7 g.), 50 ml. Ac2O, and 3 drops of concentrated H2SO4 were refluxed 7 min., and cooled to 0°. Recrystallization of the solid from AcOH gave 8.5 g. II, m. 265°. In the experiment, the researchers used Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Application In Synthesis of Methyl 1H-pyrazole-3-carboxylate)

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

Yuan, Jingli’s team published research in Analytical Chemistry in 2001 | CAS: 15366-34-4

Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4) belongs to pyrazoles. Pyrazole derivatives have been reported to exhibit a wide range of applications in medicinal chemistry and pharmacology. A large number of drugs incorporating pyrazole structure have been utilized as partial agonists for nicotinic acid receptors, antidepressants, antimicrobial agents, antiviral agents, and antifungal agents solely or along with the combination of other structural motifs.Related Products of 15366-34-4

Related Products of 15366-34-4In 2001 ,《Synthesis of a terbium fluorescent chelate and its application to time-resolved fluoroimmunoassay》 was published in Analytical Chemistry. The article was written by Yuan, Jingli; Wang, Guilan; Majima, Keisuke; Matsumoto, Kazuko. The article contains the following contents:

A new nonadentate ligand, N, N, N1, N1-[2,6-bis(3′-aminomethyl-1′-pyrazolyl)-4-phenylpyridine]tetrakis(acetic acid) (BPTA) for a Tb3+ fluorescent complex was synthesized. The Tb3+ complex is strongly fluorescent, having a large fluorescence quantum yield of 1.00 and very long fluorescence lifetime of 2.681 ms in 0.05 M borate buffer of pH 9.1. Streptavidin (SA) was labeled with BPTA by using its succinimidyl monoester, and the BPTA-Tb3+-labeled SA was used in sandwich-type time-resolved fluoroimmunoassay (TR-FIA) of α-fetoprotein (AFP) and carcinoembryonic antigen (CEA) in human sera. The Tb3+-labeled SA was also used in competitive-type TR-FIA of bensulfuron-Me (BSM) in water. The detection limits of these assays are 42 pg/mL for AFP, 70 pg/mL for CEA, and 0.4 ng/mL for BSM. In addition, a new simultaneous measurement method for AFP and CEA in a human serum sample was developed by using 4,4′-bis(1”,1”,1”,2”,2”,3”,3” -heptafluoro-4”,6”-hexanedion-6”-yl)chlorosulfo-o-terphenyl (BHHCT)-Eu3+-labeled anti-AFP antibody, biotinylated anti-CEA antibody, and BPTA-Tb3+-labeled SA. The concentrations of AFP and CEA in 39 human serum samples were determined, and the results were compared with those of the independently determined AFP and CEA by TR-FIA with a single-label method. A good correlation was obtained with the correlation coefficients of 0.991 for AFP and 0.994 for CEA. The results came from multiple reactions, including the reaction of Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Related Products of 15366-34-4)

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

Kusakiewicz-Dawid, Anna’s team published research in Molecules in 2019 | CAS: 15366-34-4

Formula: C5H6N2O2In 2019 ,《Annular tautomerism of 3(5)-disubstituted-1H-pyrazoles with ester and amide groups》 appeared in Molecules. The author of the article were Kusakiewicz-Dawid, Anna; Porada, Monika; Dziuk, Blazej; Siodlak, Dawid. The article conveys some information:

A series of disubstituted 1H-pyrazoles with Me (1), amino (2), and nitro (3) groups, as well as ester (a) or amide (b) groups in positions 3 and 5 was synthesized, and annular tautomerism was investigated using X-ray, theor. calculations, NMR, and FT-IR methods. The X-ray experiment in the crystal state showed for the compounds with Me (1a, 1b) and amino (2b) groups the tautomer with ester or amide groups at position 3 (tautomer 3), but for those with a nitro group (3b, 4), tautomer 5. Similar results were obtained in solution by NMR NOE experiments in CDCl3, DMSO-d6, and CD3OD solvents. However, tautomer equilibrium was observed for 2b in DMSO. The FT-IR spectra in chloroform and acetonitrile showed equilibrium, which can be ascribed to conformational changes of the cis/trans arrangement of the ester/amide group and pyrazole ring. Theor. anal. using the M06-2X/6-311++G(d,p) method (in vacuo, chloroform, acetonitrile, and water) and measurement of aromaticity (NICS) showed dependence on internal hydrogen bonds, the influence of the environment, and the effect of the substituent. These factors, pyrazole aromaticity and intra- and inter-mol. interactions, seem to have a considerable influence on the choice of tautomer. The results came from multiple reactions, including the reaction of Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Formula: C5H6N2O2)

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

Anderson, Erin D.’s team published research in Organic Letters in 2014 | CAS: 15366-34-4

In 2014,Anderson, Erin D.; Duerfeldt, Adam S.; Zhu, Kaicheng; Glinkerman, Christopher M.; Boger, Dale L. published 《Cycloadditions of Noncomplementary Substituted 1,2,3-Triazines》.Organic Letters published the findings.Synthetic Route of C5H6N2O2 The information in the text is summarized as follows:

The scope of the [4 + 2] cycloaddition reactions of substituted 1,2,3-triazines, bearing noncomplementary substitution with electron-withdrawing groups at C4 and/or C6, is described. The studies define key electronic and steric effects of substituents impacting the reactivity, mode (C4/N1 vs C5/N2), and regioselectivity of the cycloaddition reactions of 1,2,3-triazines with amidines, enamines, and ynamines, providing access to highly functionalized heterocycles [e.g., Me 1,2,3-triazine-4-carboxylate + benzamidine → Me 2-phenylpyrimidine-4-carboxylate (71%)].Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Synthetic Route of C5H6N2O2) was used in this study.

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

Micheel, Fritz’s team published research in Chemische Berichte in 1967 | CAS: 15366-34-4

In 1967,Micheel, Fritz; Dammert, Walter published 《Condensation products from trimethyl fluorotrimesate and α-amino-β-hydroxy compounds》.Chemische Berichte published the findings.Related Products of 15366-34-4 The information in the text is summarized as follows:

N-[6-carboxy-2,4-bis(methoxycarbonyl)phenyl]-DL-serinolactone (I) was treated with CH2N2 to form a pyrazoline which was converted to the corresponding cyclopropane derivative by elimination of N. The structures of the pyrazoline and cyclopropane derivatives were confirmed by degradation and synthesis. Condensates of DL-threonine and β-phenyl-DL-serine with methyl fluorotrimesate formed ester lactones, which on treatment with CH2N2 formed Me N-[2,4,6-(trimethoxycarbonyl)phenyl]-α-aminocrotonate and Me N-[2,4,6 (trimethoxycarbonyl)phenyl]-α-aminocinnamate, resp. In the experimental materials used by the author, we found Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Related Products of 15366-34-4)

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

Akrem, A. A.’s team published research in Tetrahedron Letters in 1973 | CAS: 15366-34-4

In 1973,Akrem, A. A.; Kvasyuk, E. I.; Mikhailopulo, I. A. published 《Unusual reaction of 3-(methoxycarbonyl)-Δ2-pyrazoline with lead tetraacetate》.Tetrahedron Letters published the findings.Name: Methyl 1H-pyrazole-3-carboxylate The information in the text is summarized as follows:

The title reaction gave 70% 3-(methoxycarbonyl)-1-[1-(methoxycarbonyl)-cyclopropyl]pyrazole (I) and 14% 3-(methoxycarbonyl)-1-[3-(methoxycarbonyl)pyrazol-1-yl]-2-pyrazoline (II). NMR, ir, and uv spectral data for I, II, 3-(methoxycarbonyl)pyrazole, and 7-acetyl-3-(methoxycarbonyl)-2-pyrazoline were determined The experimental process involved the reaction of Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Name: Methyl 1H-pyrazole-3-carboxylate)

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