pyrazoles-derivatives

On the Synthesis of Zwitterionic Heteropolycyclic Pyrazoles by a Three-Component Reaction. Some Mechanistic Considerations was written by Wamhoff, Heinrich;Bamberg, Christian;Herrmann, Stefan;Nieger, Martin. And the article was included in Journal of Organic Chemistry in 1994.COA of Formula: C5H9N3 This article mentions the following:

The novel three-component reaction involving a heterocyclic iminophosphorane, an isocyanate, and a hetarene component is applied to an aromatic pyrazole iminophosphorane I and to an analogous pyrazolone derivative The hitherto unknown zwitterionic pyrazolo[3′,4′:4,5]pyrimido[6,1-a]isoquinolines, e.g. II, pyrazolo[3′,4′:4,5]pyrimido[6,1-a]phthalazine III and pyrazolo[3′,4′:4,5]pyrido[6,1-a]pyrimidines, e.g. IV, are obtained. Addnl., the novel cycloaddition products with triazolinediones, thepyrazolo[3,4-e][1,2,4]triazolo[1,2-a][1,2,4]triazinediones, e.g. V, are described. The isolation of a dihydro compound a phthalazinium salt supports a stepwise mechanism for the zwitterion formation. While the influence of the aromaticity of the iminophosphorane component appears to be negligible, the aromaticity of the hetarene component determines the limitations of this versatile reaction. X-ray structures of 3 products as well as UV-, MS-, and NMR-spectra and semiempirical calculations confirm the zwitterionic character of the reaction products. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3COA of Formula: C5H9N3).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.COA of Formula: C5H9N3

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

Oxidative Dehydrogenative Couplings of Pyrazol-5-amines Selectively Forming Azopyrroles was written by Jiang, Bo;Ning, Yi;Fan, Wei;Tu, Shu-Jiang;Li, Guigen. And the article was included in Journal of Organic Chemistry in 2014.Related Products of 3528-58-3 This article mentions the following:

New oxidative dehydrogenative couplings of pyrazol-5-amines for the selective synthesis of azopyrrole derivatives have been described. The reaction simultaneously installs C-I and N-N bonds through iodination and oxidation; a copper-catalyzed oxidative coupling process led to azopyrroles,. E.g., in presence of I₂, TBHP, and K₂CO₃ in EtOH, dehydrogenative coupling of pyrazol-5-amine (I) gave 86% iodinated azopyrrole [(E)-II]. E.g., in presence of CuI, 1,10-phenanthroline, and TBHP in CH₂Cl₂, dehydrogenative coupling of I gave 56% (E)-III. The resulting iodo-substituted azopyrroles were employed by treatment with various terminal alkynes through Sonogashira cross-coupling leading to new azo compounds In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Related Products of 3528-58-3).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. The pyrazole ring is resistant to oxidation and reduction but the groups, such as alkyl and formyl attached to the ring, are oxidized to respective acids. Only electrolytic oxidation, ozonolysis, and a strong base cause ring opening.Related Products of 3528-58-3

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

Diphenylurea derivatives for combating methicillin- and vancomycin-resistant Staphylococcus aureus was written by Eissa, Ibrahim H.;Mohammad, Haroon;Qassem, Omar A.;Younis, Waleed;Abdelghany, Tamer M.;Elshafeey, Ahmed;Abd Rabo Moustafa, Mahmoud M.;Seleem, Mohamed N.;Mayhoub, Abdelrahman S.. And the article was included in European Journal of Medicinal Chemistry in 2017.Synthetic Route of C11H10N2O2 This article mentions the following:

A new class of diphenylurea was identified as a novel antibacterial scaffold with an antibacterial spectrum that includes highly resistant staphylococcal isolates, namely methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA & VRSA). Starting with a lead compound that carries an aminoguanidine functionality from one side and a Bu moiety on the other ring, several analogs were prepared Considering the pharmacokinetic parameters as a key factor in structural optimization, the structure-activity-relationships (SARs) at the lipophilic side chain were rigorously examined leading to the discovery of the cycloheptyloxyl analog I as a potential drug-candidate. This compound has several notable advantages over vancomycin and linezolid including rapid killing kinetics against MRSA and the ability to target and reduce the burden of MRSA harboring inside immune cells (macrophages). Furthermore, the potent anti-MRSA activity of I was confirmed in vivo using a Caenorhabditis elegans animal model. The present study provides a foundation for further development of diphenylurea compounds as potential therapeutic agents to address the burgeoning challenge of bacterial resistance to antibiotics. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8Synthetic Route of C11H10N2O2).

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Synthetic Route of C11H10N2O2

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

Features of the complex formation of platinum(II), palladium(II), and cobalt(II) with 3,5-dimethyl-1-carbamidopyrazole was written by Shebaldova, A. D.;Safronova, L. A.. And the article was included in Russian Journal of Coordination Chemistry (Translation of Koordinatsionnaya Khimiya) in 1995.HPLC of Formula: 934-48-5 This article mentions the following:

The interaction of Pt(II), Pd(II), and Co(II) salts with 3,5-dimethyl-1-carbamidopyrazole (HL) was studied. Complexes of various compositions and structures are formed, depending on the nature of the metal, the type of salt, and the ratio between the reagents (M:L = 1:1 or 1:2). In the case of K₂MCl₄ [M = Pt(II), Pd(II),], M(HL)Cl₂ chelate cis complexes with HL coordinated via the pyridine N atom of the cycle and via the N atom of the amino group are formed at the equimolar ratio between the reagents. At the ratio M:HL = 1:2, the PdL₂ chelate and the [Pt(HL’)(L’)Cl]₂ bridging complex with the product of decarbamoylization of the ligand, namely, 3,5-dimethylpyrazole (HL’), are formed for Pd(II) and Pt(II), resp. In distinction to K₂MCl₄, the reaction of PdCl₂ and CoCl₂ with HL leads, in all cases, to the destruction of the ligand and to the formation of ML’₂Cl₂ complexes. The coordination environment of the metal in the complexes is determined by DTA and IR spectroscopy. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5HPLC of Formula: 934-48-5).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.HPLC of Formula: 934-48-5

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

Iodine-Promoted Synthesis of Dipyrazolo/Diuracil-Fused Pyridines and o-Amino Diheteroaryl ketones via Oxidative Domino Annulation of 2/4-Methylazaarenes was written by Zhang, Xin-Ke;Miao, Xiao-Yu;Jiang, Hui-Ru;Ge, Fei;Sun, Jia-Chen;Zhang, Rui-Ying;Ouyang, Qin;Fan, Wei-Yu;Zthu, Yan-Ping;Sun, Yuan-Yuan. And the article was included in Advanced Synthesis & Catalysis in 2021.Recommanded Product: 1-Ethyl-1H-pyrazol-5-amine This article mentions the following:

The iodine-promoted oxidative domino annulation and carbonylation process has been developed for the synthesis of biol. important azaarene-substituted bis-pyrazolo[3,4-b:4′,3′-e]pyridines (BPPs) I (R = quinolin-2-yl, 1,3-benzoxazol-2-yl, pyridin-4-yl, etc.; R¹ = Me, Ph, t-Bu, 4-fluorophenyl; R² = H, Ph, 2,5-dimethylphenyl, 4-methylphenyl), diuracilpyridines II [R³ = 7-fluoroquinolin-2-yl, 1,8-naphthyridin-2-yl, 1,3-benzothiazol-2-yl, etc.] and o-amino diheteroaryl ketones III [R⁴ = H, Me, Cl, OEt, etc.; R⁵ = H, Me; R⁶ = Me, Et, Ph]. The domino procedure proceeded with easily available Me azaarenes such as 2-Me quinoline, 2-methylquinazolin-4(3H)-one, 2-methylbenzothiazole, etc. 6-amino-1,3-dimethylpyrimidine-2,4-dione and substituted 5-aminopyrazoles IV (R⁷ = H, Me, Ph, t-Bu, etc.; R⁸ = H, Me, Et, Ph, etc.). This protocol is a simple and metal-free approach which exhibits high functional group compatibility and broad substrates scope. Moreover, this transformation can be applied for the preparation of dipyrazolo/diuracil-fused pyridines I (R = quinolin-2-yl; R¹ = Me; R² = Ph)/II (R³ = quinolin-2-yl) on a gram scale. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Recommanded Product: 1-Ethyl-1H-pyrazol-5-amine).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Recommanded Product: 1-Ethyl-1H-pyrazol-5-amine

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

Potent antagonists of gonadotropin releasing hormone receptors derived from quinolone-6-carboxamides was written by Walsh, Thomas F.;Toupence, Richard B.;Young, Jonathan R.;Huang, Song X.;Ujjainwalla, Feroze;DeVita, Robert J.;Goulet, Mark T.;Wyvratt, Matthew J. Jr.;Fisher, Michael H.;Lo, Jane-Ling;Ren, Ning;Yudkovitz, Joel B.;Yang, Yi Tien;Cheng, Kang;Smith, Roy G.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2000.Application of 3528-58-3 This article mentions the following:

SAR studies which focused upon the C(6) position of a recently described series of quinolone gonadotropin-releasing hormone antagonists are reported. Synthetic access to diverse quinolone-6-carboxamides was achieved via the Pd-catalyzed aminocarbonylation reactions of a 4-hydroxy-6-iodoquinolone with various amines. 4-Pyrimidinamine-derived amides were especially potent, functional antagonists of rat and human GnRH receptors. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Application of 3528-58-3).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. As is the case with imidazoles, the pyrazole ring offers many opportunities to create new multiring systems that incorporate this heterocycle. Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.Application of 3528-58-3

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

Experimental and theoretical spectroscopic and electronic properties enriched with NBO analysis for 1-methyl-3-nitropyrazole and 1-methyl-5-nitropyrazole was written by Regiec, Andrzej;Wojciechowski, Piotr;Mastalarz, Henryk. And the article was included in Journal of Molecular Structure in 2014.Application In Synthesis of 1-Methyl-3-nitro-1H-pyrazole This article mentions the following:

Both exptl. and calculated spectral and electronic properties of two isomers 1-methyl-3-nitropyrazole and 1-methyl-5-nitropyrazole have been demonstrated and discussed in details based on normal mode anal. The fully anharmonic IR spectra with calculated anharmonic intensities for fundamental bands, overtones and combination bands were also reported. The stability of title mols. arising from hyper conjugative interaction have been demonstrated using natural bond orbital (NBO) anal. Electron affinities clearly point that 1-methyl-5-nitropyrazole should be much more susceptible to reduction process than 1-methyl-3-nitropyrazole what has been exptl. confirmed by measurement of reduction potential. For 1-methyl-5-nitropyrazole, unambiguous assignment of values of proton and carbon chem. shifts to appropriate protons and carbons has been made thanks to full anal. of ¹H and ¹³C NMR spectra and two dimensional (2D) ¹H-¹H and ¹H-¹³C NMR COSY spectroscopy. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1Application In Synthesis of 1-Methyl-3-nitro-1H-pyrazole).

1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1) belongs to pyrazole derivatives. As is the case with imidazoles, the pyrazole ring offers many opportunities to create new multiring systems that incorporate this heterocycle. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, antidiabetic and antibacterial activities.Application In Synthesis of 1-Methyl-3-nitro-1H-pyrazole

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

Nitropyrazoles. 3. Synthesis of C-(diformylmethyl)nitropyrazoles was written by Dalinger, I. L.;Shkineva, T. K.;Shevelev, S. A.;Krat, V.;Arnold, Z.. And the article was included in Izvestiya Akademii Nauk, Seriya Khimicheskaya in 1993.Category: pyrazoles-derivatives This article mentions the following:

A double Vilsmeier formylation of a C-Me group in pyrazole derivatives occurs when a nitro group is adjacent to the Me group. Thus, dimethylnitropyrazole I was treated with DMF and POCl₃ to give diperchlorate II, which was hydrolyzed to bis(diformylmethyl) derivative III. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4Category: pyrazoles-derivatives).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.Category: pyrazoles-derivatives

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

Reactions of N-aminopyrazoles with halogenating reagents and synthesis of 1,2,3-triazines was written by Osawa, Akio;Kaiho, Terumitsu;Ito, Takashi;Okada, Mamiko;Kawabata, Chikako;Yamaguchi, Kentaro;Igeta, Hiroshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1988.Synthetic Route of C5H7ClN2 This article mentions the following:

Reactions of N-aminopyrazoles with halogenating reagents (Cl₂, Br₂, I₂, BrCl, ICl, IBr, N-chlorosuccinimide, and N-bromosuccinimide) were examined Some of these reagents preferentially leas to oxidation of the amino group to give the corresponding 1,2,3-triazines as major products, while others mainly gave either or both of 1-amino-4-halopyrazoles and 5-halo-1,2,3-triazines as the result of halogenation of the 4-position of the pyrazole ring prior to the oxidation of the amino group. In some cases, the oxidation of the amino group and the halogenation of the pyrazole ring proceeded concurrently to form not only the unhalogenated triazines but also the 1-amino-4-halopyrazines and the 5-halotriazines. Various reagents and reaction conditions were explored to utilize the reaction for the synthesis of halogenated and unhalogenated 1,2,3-triazines. In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8Synthetic Route of C5H7ClN2).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Synthetic Route of C5H7ClN2

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

A simple and environmentally benign nitration of pyrazoles by impregnated bismuth nitrate was written by Ravi, P.;Gore, Girish M.;Tewari, Surya P.;Sikder, Arun K.. And the article was included in Journal of Heterocyclic Chemistry in 2013.HPLC of Formula: 54210-32-1 This article mentions the following:

A facile, rapid, and environmentally friendly synthesis of nitropyrazoles in good yields was reported using silica-bismuth nitrate and silica-sulfuric acid-bismuth nitrate at room temperature The relatively non-toxic nature, ease of handling, easy availability, and low cost make the present procedure attractive for the nitration of a wide variety of diazoles in drug and pharmaceutical industries. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1HPLC of Formula: 54210-32-1).

1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. HPLC of Formula: 54210-32-1

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