Tag: 100-200

An efficient procedure for the synthesis of pyrazolo[3,4-d][1,3]thiazin-4-ones was written by Vicentini, Chiara B.;Veronese, Augusto C.;Guccione, Salvatore;Guarneri, Mario;Manfrini, Maurizio;Giori, Paolo. And the article was included in Heterocycles in 1993.Computed Properties of C8H15N3 This article mentions the following:

Trichloromethyl chloroformate reacts with N-(1-alkyl/aryl-5-pyrazolyl) thiocarboxamides to give pyrazolo[3,4-d][1,3]thiazin-4-ones I (R¹-R² = alkyl, etc.) while it reacts with N-(3-methyl-5-pyrazolyl)thiobenzamide to give the pyrazolo[1,5-c][1,3,5]thiadiazine-4-one (II). Heating under reflux in formic acid of I homologs bearing a tert-Bu group linked to pyrazole N-1 atom afforded dealkylated derivatives of I. In the experiment, the researchers used many compounds, for example, 1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2Computed Properties of C8H15N3).

1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. 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.Computed Properties of C8H15N3

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

Bridgehead nitrogen heterocycles. Part II. Reactions of 4-bromo-3-methyl-1-substituted-5-pyrazolones with 4-amino-3-mercapto-5-substituted-s-triazoles and cyclic thioureas was written by Chadha, Vijay K.;Sharma, G. R.. And the article was included in Journal of the Indian Chemical Society in 1990.HPLC of Formula: 51395-52-9 This article mentions the following:

Bromomethylpyrazolones I (R = H, Ph) undergo cyclocondensation with aminomercaptotriazoles II (R¹ = Me, Et, Pr, Ph, 2-HOC₆H₄, 3-O₂NC₆H₄) to give pyrazolotriazolothiadiazines III. I also reacts with cyclic thioureas, e.g. 2-mercapto-1-imidazoline gave pyrazoloimidazolothiazole IV. In the experiment, the researchers used many compounds, for example, 4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9HPLC of Formula: 51395-52-9).

4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.HPLC of Formula: 51395-52-9

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

Pyrazole studies. 21. Synthesis of 3-dialkylaminomethyl-5-methyl-4-substituted-1H-pyrazoles. Selective functionalization of one methyl group via N-nitration of 3,5-dimethyl-4-substituted-1H-pyrazoles was written by Lammers, H.;Vollinga, R.;Zandbergen, P.;Cohen-Fernandes, P.;Habraken, C. L.. And the article was included in Journal of Heterocyclic Chemistry in 1995.Synthetic Route of C5H7ClN2 This article mentions the following:

Treatment of 3,5-dimethyl-1,4-dinitro-1H-pyrazole and 4-halo-3,5-dimethyl-1-nitro-1H-pyrazoles with secondary amines in acetonitrile, in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), gave 3-[(dialkylamino)methyl]-1H-pyrazoles in good to excellent yields. In this way one of the, in general, inert Me groups of 3,5-dimethyl-4-substituted-1H-pyrazoles is functionalized creating a new synthetic route to azoles containing a coordinating substituent. 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. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. Pyrazoles and pyrimidines have diverse biological and pharmacological activities. There are a number of antimicrobial compounds containing pyrazole moiety as the core unit. Pyrazofurin is important antimicrobial drug and 2-methylpyrimidine-4-ylamine derivatives I and II were found to be effective inhibitors of Escherichia coli PDHc-E1 with antibacterial and antifungal activity.Synthetic Route of C5H7ClN2

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

Cascade Wolff Rearrangement/Acylation: A Metal-Free and Eco-Friendly Approach for 4-Hydroxy-pyrazolo[3,4-b]pyridin-6-ones and N-Pyrazole Amides Synthesis from 5-Aminopyrazoles and α-Diazoketones was written by Zhang, Xiang-Jin;Zhang, Jie;Xu, Yu-Ning;Li, Yi-Ming;Chi, Man;Yan, Yu;Wu, Rui-Xue;Zhang, Hui-Ru;Zhu, Yan-Ping. And the article was included in Journal of Organic Chemistry in 2021.Formula: C8H15N3 This article mentions the following:

A highly chemoselective cascade Wolff rearrangement/acylation reaction between 5-aminopyrazoles and diazo compounds has been developed. The protocol can facilitate the switchable synthesis of 4-hydroxy-pyrazolo[3,4-b]pyridin-6-ones I (R¹ = Me, Et, Ph, etc.; R² = Ph, t-Bu, 2-naphthyl, etc.; R³ = Ph, 4-MeOC₆H₄, 3-thienyl, etc.) and N-pyrazole amides II (R¹ = Me, t-Bu, Ph; R² = Ph, 4-FC₆H₄, 2-naphthyl, etc.; R³ = Me, c-hexyl, Ph, etc.; R⁴ = Me, Et) with the merits of a broad substrate scope, high functional group compatibility, and green and sustainable performance manner. All reactions proceeded efficiently without any catalyst and additives (acid and base) and resulted in the release of benign N₂, wherein di-Et carbonate served as a green benign solvent. In the experiment, the researchers used many compounds, for example, 1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2Formula: C8H15N3).

1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2) 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. Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.Formula: C8H15N3

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

Transition metal complexes with pyrazole-based ligands Part 12. Characterisation and thermal decomposition of CuCl₂ complexes with di- and trisubstituted pyrazoles was written by Szecsenyi, K. Meszaros;Leovac, V. M.;Jacimovic, Z. K.;Cesljevic, V. I.;Kovacs, A.;Pokol, G.. And the article was included in Journal of Thermal Analysis and Calorimetry in 2001.COA of Formula: C6H9N3O This article mentions the following:

The synthesis of copper(II) chloride complexes with 3,5-dimethylpyrazole, 1-carboxamide-3,5-dimethylpyrazole, 5-amino-4-carboxamide-1-phenylpyrazole and 4-acetyl-3-amino-5-methylpyrazole is described. The compounds were characterized by elemental anal., FTIR spectroscopy, thermal methods, magnetic moment and molar conductivity measurements. Elimination of the carboxamide group from the 1-carboxamide-3,5-dimethylpyrazole takes place to give 3,5-dimethylpyrazole complexes. Thermal decomposition of the dichloro(3,5-dimethylpyrazole)copper(II) complex results in an unstable intermediate with a stoichiometric composition The decomposition of the other compounds is continuous. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5COA of Formula: C6H9N3O).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) 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 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: C6H9N3O

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

Bromination of 2-pyrazolines was written by Elguero, Jose;Jacquier, Robert. And the article was included in Compt. Rend. in 1963.Category: pyrazoles-derivatives This article mentions the following:

N-Substituted pyrazolines brominate readily at position 3 but with difficulty at position 4, while pyrazolines not N-substituted give the corresponding pyrazoles, which brominate at the 4-position when this position is unsubstituted. Equimolar proportions of Br and 5-methylpyrazoline (I) in CHCl₃ gave an unstable compound which had a nuclear magnetic resonance (n.m.r.) spectrum with a doublet at 7.32 p.p.m. and was apparently 1-bromo-3-methylpyrazoline (II). Without desiccation II rapidly liberated HBr to give a hydrobromide of 3-methylpyrazole, identified by n.m.r. spectrum. Bromination of I with 2 moles Br gave the hydrobromide of 3-methyl-4-bromopyrazole, m. 185-7°, identified by n.m.r. spectrum. Bromination of 3,5,5-trimethylpyrazoline (III) gave, in addition to a small amount of the hydrobromide of III, 1-bromo-3,5,5-trimethylpyrazoline (IV), b_0.5 58°, m. 16°, in 83% yield. IV liberated iodine from aqueous acidic KI, precipitated AgBr from a pyridine solution of AgNO₃, was reduced by SO₂ to III, gave no NH band in its infrared spectrum, and in its n.m.r. spectrum gave bands at 8.55 (gem-dimethyl), 7.86 (3-methyl), and a quartet at 8.01 p.p.m. (2 protons at 4). IV, refluxed in AcOH, gave a black solid containing the hydrobromide of N-bromo-3,4,5-trimethylpyrazole, which was converted by MeONa in MeOH to the hydrobromide of 3,4,5-trimethylpyrazole (V), m. 257°. The change from IV to V is apparently a reverse pinacol transformation. Similarly, 1,3,5,5-tetramethylpyrazoline, b₂₅ 61° (from III and MeI), gave a 20% yield of 1,3,4,5-tetramethylpyrazole (picrate m. 192°). In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8Category: pyrazoles-derivatives).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).Pyrazole used as a ligand to prepare organometallic compounds. Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.Category: pyrazoles-derivatives

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

NOE difference spectroscopy as a versatile tool for spectral and structural assignment in various N-1 substituted pyrazoles was written by Holzer, Wolfgang. And the article was included in Tetrahedron in 1991.HPLC of Formula: 54210-32-1 This article mentions the following:

NOE difference spectroscopy is proposed as a simple method for the discrimination between pyrazole H-3 and H-5 resonances in various 1-substituted and 1,4-disubstituted pyrazoles as well as for the differentiation between isomeric pairs of 1,3,4- and 1,4,5-trisubstituted, or 1,3- and 1,5-disubstituted pyrazoles, utilizing a through-space connection between a pyrazole H-5 proton and protons of the N-1 substituent. 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. 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.HPLC of Formula: 54210-32-1

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

Investigation of thermal stability of high-melting thermostable explosives was written by Falyakhov, I. F.;Sharnin, G. P.;Safin, N. M.;Saifullin, I. Sh.;Fassakhov, R. Kh.. And the article was included in Proceedings of the International Pyrotechnics Seminar in 1995.Electric Literature of C4H5N3O2 This article mentions the following:

The kinetics is studied of thermal decomposition of aromatic and heteroaromatic organic compounds and their salts. The thermal stability is studied of high-melting explosives, nitro derivatives of aromatic and heteroaromatic organic compounds (nitropyrroles, nitroimidazoles, nitropyrazoles, nitro derivatives of 1,2,4-triazoles, nitropyridines and their metal salts, benzofurazanes and benzofuroxanes). In the experiment, the researchers used many compounds, for example, 1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1Electric Literature of C4H5N3O2).

1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1) 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. 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.Electric Literature of C4H5N3O2

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

Mass spectrometry of nitroazoles. I. The mass spectra of methyl substituted nitropyrazoles was written by Luijten, W. C. M. M.;Van Thuijl, J.. And the article was included in Organic Mass Spectrometry in 1979.Category: pyrazoles-derivatives This article mentions the following:

The mass spectra of all isomers of methylnitropyrazoles are reported. Generally, the spectra are characteristic of nitropyrazoles. In some cases however, ortho effects occur, which were recognizable by the primary loss of •OH, H₂O, •CHO and HCHO. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1Category: pyrazoles-derivatives).

1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. 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. Category: pyrazoles-derivatives

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

High Throughput Synthesis of Extended Pyrazolo[3,4-d]dihydropyrimidines was written by Ryabukhin, Sergey V.;Granat, Dmitry S.;Plaskon, Andrey S.;Shivanyuk, Alexander N.;Tolmachev, Andrey A.;Volovenko, Yulian M.. And the article was included in ACS Combinatorial Science in 2012.Electric Literature of C8H15N3 This article mentions the following:

Fused pyrazolo[3,4-d]pyrimidines such as I (R = Ph, 4-MeOC₆H₄, 4-ClC₆H₄, 5-phenyl-2-furanyl, 1-phenyl-4-pyrazolyl, 3,4-Me₂C₆H₃, 3-F₃CC₆H₄, 3-Me-2-thienyl, 3-ClC₆H₄, 5-Me-2-furanyl, 3,5-dimethyl-4-isoxazolyl, 3,4-Cl₂C₆H₃, 2-FC₆H₄, 3-FC₆H₄, 4-Me₂NC₆H₄, 2-F₂CHOC₆H₄; R¹ = H; R² = H, F₃C, Me₂NSO₂, 1-pyrrolidinylsulfonyl, 1-piperidinylsulfonyl, 4-morpholinylsulfonyl; R¹R² = benzo) were prepared in two steps from 1-substituted-5-pyrazoleamines such as 1-isopropyl-5-pyrazoleamine, heteroaryl chlorides such as 2-chloropyridine, and aldehydes such as benzaldehyde. N-heteroaryl 5-pyrazoleamines such as II (R¹ = H; R² = H, F₃C, 1-piperidinylsulfonyl; R¹R² = benzo) were generated by base-mediated condensation of 5-pyrazoleamines such as 1-phenyl-3-methyl-5-pyrazoleamine with heteroaryl chlorides such as 2-chloropyridine; heating the heteroaryl pyrazoleamines with aryl aldehydes or isatins either in a sealed tube with trimethylsilyl chloride or in glacial acetic acid followed by crystallization yielded pyrazolo[3,4-d]pyrimidines. Reaction of N-heteroaryl 5-pyrazoleamines with cyclohexanone provided N-heteroaryl 4-(1-cyclohexen-1-yl)-5-pyrazoleamines rather than spirocyclohexanepyrazolopyrimidines. A library of > 200 pyrazolo[3,4-d]pyrimidines were prepared; the distribution of the library members within ranges of lipophilicity, mol. weight, hydrogen bond acceptor and donor count, and polar surface area was determined In the experiment, the researchers used many compounds, for example, 1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2Electric Literature of C8H15N3).

1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Pyrazoles and pyrimidines have diverse biological and pharmacological activities. There are a number of antimicrobial compounds containing pyrazole moiety as the core unit. Pyrazofurin is important antimicrobial drug and 2-methylpyrimidine-4-ylamine derivatives I and II were found to be effective inhibitors of Escherichia coli PDHc-E1 with antibacterial and antifungal activity.Electric Literature of C8H15N3

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