pyrazoles-derivatives

Morgentin, Remy’s team published research in Synthetic Communications in 2012-01-01 | 118430-74-3

Synthetic Communications published new progress about Buchwald-Hartwig reaction. 118430-74-3 belongs to class pyrazoles-derivatives, and the molecular formula is C7H11N3, Electric Literature of 118430-74-3.

Morgentin, Remy; Barlaam, Bernard; Foote, Kevin; Hassall, Lorraine; Hawkins, Janet; Jones, Clifford D.; Le Griffon, Antoine; Peru, Aurelien; Ple, Patrick published the artcile< Two-Directional Approach for the Rapid Synthesis of 2,4-Bis-Aminoaryl Pyridine Derivatives>, Electric Literature of 118430-74-3, the main research area is aminoarylpyridine preparation coupling palladium; pyridine aminoaryl preparation coupling palladium; Buchwald Hartwig regioselective nucleophilic substitution bisaminoarylpyridine preparation.

We have developed two different approaches in parallel to rapidly access 2,4-bis(aminoaryl)pyridine compounds, e.g., I, from a common starting material. The C-4/C-2 approach uses palladium-mediated coupling reactions to sequentially functionalize C-4 and then C-2. An alternative C-2/C-4 route uses a regioselective SNAr reaction to first substitute at C-2 then subsequently at C-4 by a palladium-mediated reaction. Both approaches have been used successfully to provide a range of 2,4-bis(aminoaryl)pyridine compounds

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

Chang, Kuei-Choo’s team published research in Australian Journal of Chemistry in 1979-08-31 | 13808-65-6

Australian Journal of Chemistry published new progress about Nitration. 13808-65-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, HPLC of Formula: 13808-65-6.

Chang, Kuei-Choo; Grimmett, M. Ross; Ward, David D.; Weavers, Rex T. published the artcile< The nitration of brominated pyrazoles in aqueous sulfuric acid>, HPLC of Formula: 13808-65-6, the main research area is bromopyrazole nitration substituent; pyrazole bromo nitration substituent.

Nitration in 80% H2SO4 of 4-bromopyrazoles gives rise to considerable nitrodebromination. Compounds with no alkyl or aryl substituent on N give only the 4-nitro products, except 4-bromo-3-phenylpyrazole which gives the p-nitrophenyl compound N-Alkyl-4-bromopyrazoles give products of nitrodebromination as well as those arising from nitration in the 3- and/or 5-positions. N-Aryl-4-bromopyrazoles can also undergo nitration of the aryl substituent.

Australian Journal of Chemistry published new progress about Nitration. 13808-65-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, HPLC of Formula: 13808-65-6.

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

Vorobyeva, Evgeniya’s team published research in ACS Catalysis in 2020-10-02 | 13788-92-6

ACS Catalysis published new progress about Adsorption (of CuI). 13788-92-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, Recommanded Product: 1-(4-Bromophenyl)-1H-pyrazole.

Vorobyeva, Evgeniya; Gerken, Viktoria C.; Mitchell, Sharon; Sabadell-Rendon, Albert; Hauert, Roland; Xi, Shibo; Borgna, Armando; Klose, Daniel; Collins, Sean M.; Midgley, Paul A.; Kepaptsoglou, Demie M.; Ramasse, Quentin M.; Ruiz-Ferrando, Andrea; Fako, Edvin; Ortuno, Manuel A.; Lopez, Nuria; Carreira, Erick M.; Perez-Ramirez, Javier published the artcile< Activation of Copper Species on Carbon Nitride for Enhanced Activity in the Arylation of Amines>, Recommanded Product: 1-(4-Bromophenyl)-1H-pyrazole, the main research area is graphitic carbon nitride copper activation amine arylation.

We report the promoting effect of graphitic carbon nitride in Cu-catalyzed N-arylation. The abundance of pyridinic coordination sites in this host permits the adsorption of copper iodide from the reaction medium. The key to achieving high activity is to confine active Cu species on the surface, which is accomplished by introducing atomically dispersed metal dopants to block diffusion into the bulk of the carrier. The alternative route of incorporating metal during the synthesis of graphitic carbon nitride is ineffective as Cu is thermodynamically more stable in inactive subsurface positions. A combination of X-ray absorption, X-ray photoelectron, and ESR spectroscopy, d. functional theory, and kinetic Monte Carlo simulations is employed to determine the location and associated geometry as well as the electronic structure of metal centers. N-Arylation activity correlates to the surface coverage by copper, which varies during the reaction due to an interplay between site formation via adsorption from the reaction medium and deactivation by diffusion into the bulk of the material, and is highest when an Fe dopant is used to hinder such movement through the lattice.

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

Castellanos, Maria Luisa’s team published research in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1985-06-30 | 17827-61-1

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Hydrolysis kinetics. 17827-61-1 belongs to class pyrazoles-derivatives, and the molecular formula is C6H8N2O2, SDS of cas: 17827-61-1.

Castellanos, Maria Luisa; Llinas, Montserrat; Bruix, Marta; De Mendoza, Javier; Martin, M. Rosario published the artcile< NN'-linked biazoles. Part 4. Nucleophilic substitution in quaternary salts of NN'-linked biazoles and related systems>, SDS of cas: 17827-61-1, the main research area is nucleophile substitution biazolyl cation azolylpyridinium; pyridinium azolyl substitution nucleophile.

Some di- and monocationic N,N’-linked biazoles and quaternized 1-(N-azolyl)pyridinium ions were prepared and their reactions with nucleophiles were studied. Although the pyrrolyl nucleus is a poor leaving group in these reactions, in other cases nucleophilic attack readily occurs at an azolyl C, with subsequent elimination of the N substituent. E.g., reaction of dication I with NaCN in H2O at room temperature for 18 h gave 80% 2-cyano-1-methylbenzimidazole and 7% 1-methylbenzimidazol-2-one.

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

Elie, Jonathan’s team published research in Molecules in 2021 | 54346-19-9

Molecules published new progress about Fused heterocyclic compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 54346-19-9 belongs to class pyrazoles-derivatives, and the molecular formula is C6H5ClN4S, Application of C6H5ClN4S.

Elie, Jonathan; Fruit, Corinne; Besson, Thierry published the artcile< Microwave-assisted sequential one-pot synthesis of 8-substituted pyrazolo[1,5-a][1,3,5]triazines>, Application of C6H5ClN4S, the main research area is aminopyrazole ethoxycarbonyl isothiocyanate microwave assisted heterocyclization; methylsulfanyl pyrazolotriazinone preparation; 5-aza-9-deazapurines; microwave-assisted chemistry; one-pot synthesis; pyrazolo[1,5-a][1,3,5]triazines.

A convenient sequential one-pot approach for the synthesis of an array of 14 pyrazolo[1,5-a][1,3,5]triazines, I [R = H, Br, CN, etc] substituted in C8 by halogen (Br), various functions (CN and CO2Et) and alkyl or (het)aryl groups was reported. This study confirmed the interest of combining the efficient heating obtained under dielec. microwave heating and the achievement of sequential one-pot reactions, avoiding the tedious work-up and purification of intermediate compounds, achieving sustainable synthesis processes. Considering usual conventional methods, this microwave protocol was featured by advantages in terms of yields, reaction times, and convenient gram scale synthesis.

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

Kwiatkowski, Jacek’s team published research in Journal of Medicinal Chemistry in 2020 | CAS: 957345-28-7

4-Bromo-5-cyclopropyl-1H-pyrazole(cas: 957345-28-7) belongs to pyrazoles. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, antipyretic, neuroleptic, anticonvulsant, antiarrhythmic, sedative, muscle relaxant, monoamine oxidase inhibitory, anti-inflammatory, antidiabetic and antibacterial activities. Quality Control of 4-Bromo-5-cyclopropyl-1H-pyrazole

Kwiatkowski, Jacek; Liu, Boping; Pang, Shermaine; Binte Ahmad, Nur Huda; Wang, Gang; Poulsen, Anders; Yang, Haiyan; Poh, Yong Rui; Tee, Doris Hui Ying; Ong, Esther; Retna, Priya; Dinie, Nurul; Kwek, Perlyn; Wee, John Liang Kuan; Manoharan, Vithya; Low, Choon Bing; Seah, Peck Gee; Pendharkar, Vishal; Sangthongpitag, Kanda; Joy, Joma; Baburajendran, Nithya; Jansson, Anna Elisabet; Nacro, Kassoum; Hill, Jeffrey; Keller, Thomas H.; Hung, Alvin W. published an article on January 23 ,2020. The article was titled 《Stepwise Evolution of Fragment Hits against MAPK Interacting Kinases 1 and 2》, and you may find the article in Journal of Medicinal Chemistry.Quality Control of 4-Bromo-5-cyclopropyl-1H-pyrazole The information in the text is summarized as follows:

Dysregulation of translation initiation factor 4E (eIF4E) activity occurs in various cancers. Mitogen-activated protein kinase (MAPK) interacting kinases 1 and 2 (MNK1 and MNK2) play a fundamental role in activation of eIF4E. Structure-activity relationship-driven expansion of a fragment hit led to discovery of dual MNK1 and MNK2 inhibitors based on a novel pyridine-benzamide scaffold. The compounds possess promising in vitro and in vivo pharmacokinetic profiles and show potent on target inhibition of eIF4E phosphorylation in cells. In the experiment, the researchers used 4-Bromo-5-cyclopropyl-1H-pyrazole(cas: 957345-28-7Quality Control of 4-Bromo-5-cyclopropyl-1H-pyrazole)

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

Li, Weipeng’s team published research in Journal of the American Chemical Society in 2019 | CAS: 930-36-9

1-Methylpyrazole(cas: 930-36-9) belongs to pyrazoles. Pyrazoles and their related multiring analogs are common elements of a wide variety of bioactive compounds. These ring structures are rare in nature. A consequence of this is that they have previously been thought to be poor moieties to include in potential new drugs. Quality Control of 1-Methylpyrazole

Li, Weipeng; Yuan, Dandan; Wang, Guoqiang; Zhao, Yue; Xie, Jin; Li, Shuhua; Zhu, Chengjian published an article on February 20 ,2019. The article was titled 《Cooperative Au/Ag Dual-Catalyzed Cross-Dehydrogenative Biaryl Coupling: Reaction Development and Mechanistic Insight》, and you may find the article in Journal of the American Chemical Society.Quality Control of 1-Methylpyrazole The information in the text is summarized as follows:

In the presence of (Me2S)AuCl and AgOAc, pyrazoles such as 1-phenylpyrazole underwent chemoselective and regioselective oxidative dehydrogenative coupling reactions with fluorinated arenes and pyridines such as 2,3,5,6-tetrafluoropyridine mediated by PhI(OAc)2 in 1,4-dioxane to yield (fluoroaryl)pyrazoles such as I. The mechanism of the oxidative coupling reaction was studied by determination of the reaction kinetics, kinetic isotope effects, and deuterium exchange, by generation and preparation of gold and silver complexes as potential intermediates, and by DFT calculations of transition state structures and energies for arene metalation, transmetalation, and reductive elimination reactions. Silver acetate is determined to be is the actual catalyst for C-H activation of electron-poor arenes, rather than gold(I) complexes. A mechanism of gold/silver dual catalysis is proposed, in which silver is responsible for the activation of electron-poor fluoroarenes via a concerted metalation-deprotonation pathway, and gold is responsible for the activation of electron-rich pyrazoles via an electrophilic aromatic substitution process. Kinetic studies reveal that C-H activation of pyrazoles by fluoroarylgold complexes is most likely the rate-limiting step. The experimental part of the paper was very detailed, including the reaction process of 1-Methylpyrazole(cas: 930-36-9Quality Control of 1-Methylpyrazole)

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

Gilman, Norman W.’s team published research in Journal of Heterocyclic Chemistry in 1977 | 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.Recommanded Product: 15366-34-4

In 1977,Gilman, Norman W.; Holland, Betty C.; Walsh, Gregory R.; Fryer, R. Ian published 《Nucleophilic displacement of aromatic fluorine. Part V. Use of nitrogen heterocycles as nucleophiles》.Journal of Heterocyclic Chemistry published the findings.Recommanded Product: 15366-34-4 The information in the text is summarized as follows:

I (R = F) reacted with imidazole, 2-methylimidazole, 3,5-bis(acetoxymethyl)pyrazole, pyrrole, di-Et 2-methyl-4,5-imidazoledicarboxylate, Me pyrrole-2-carboxylate, di-Me pyrazole-3,5-dicarboxylate, and Me pyrazole-3-carboxylate to give N-aryl heterocycles, e.g., II. In some cases the analogous reaction with I (R = Cl) failed to occur. Some substitution reactions of other aromatic fluorides were also examined The results came from multiple reactions, including the reaction of Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Recommanded Product: 15366-34-4)

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

Suh, Jeehee’s team published research in Bulletin of the Korean Chemical Society in 2012 | CAS: 20154-03-4

3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4) 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.Formula: C4H3F3N2

Formula: C4H3F3N2In 2012 ,《Diversification of pyrazoles by microwave-assisted ligand free copper catalyzed N-arylation》 appeared in Bulletin of the Korean Chemical Society. The author of the article were Suh, Jeehee; Kang, Hee Sung; Kim, Ji-Eun; Yum, Eul Kgun. The article conveys some information:

Simple and efficient N-arylation of pyrazoles was achieved using microwave-assisted catalytic Cu reactions without organic ligands and with short reaction times. The N-arylation of pyrazole could be extended to various substituted pyrazoles and aryl halides. Yields of N-arylpyrazoles were highly dependent on the steric and electronic effects of the pyrazole substituents. Further functionalization of N-arylated iodopyrazoles in Cu- and Pd-catalyzed coupling reactions exhibited promising results for the diversification of pyrazoles. In the experiment, the researchers used 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Formula: C4H3F3N2)

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

Saakyan, A. A.’s team published research in Russian Journal of General Chemistry in 2011 | 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.Safety of Methyl 1H-pyrazole-3-carboxylate

Safety of Methyl 1H-pyrazole-3-carboxylateIn 2011 ,《Esterification of pyrazole-3- and 4-carboxylic acids》 appeared in Russian Journal of General Chemistry. The author of the article were Saakyan, A. A.. The article conveys some information:

The esterification of pyrazole-3- and 4-carboxylic acids with MeOH was described.Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Safety of Methyl 1H-pyrazole-3-carboxylate) was used in this study.

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