Month: January 2023

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

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

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

Blocking and Deblocking of Diisocyanate to Synthesize Polyurethanes was written by Jana, Sourita;Samanta, Debasis;Fahad, Mir Muhammad;Jaisankar, Sellamuthu N.;Kim, Hongdoo. And the article was included in Polymers (Basel, Switzerland) in 2021.Electric Literature of C9H7BrN2 This article mentions the following:

Diisocyanates, particularly toluene diisocyanate (TDI), are useful for the preparation of various polyurethanes with specific applications as leather-like materials, adhesives and insoles, etc. Blocking agents can be used for the operational simplicity and to reduce the hazards of TDI. In this paper, we reported the use of 3-(4-bromo-phenyl)-1H-pyrazole to block toluene diisocyanate (TDI). FTIR, NMR, thermogravimetric anal., contact angle anal. and differential scanning calorimetry (DSC) were used for the characterization. The effectiveness of the blocking was confirmed by spectroscopic techniques. The DSC thermogram showed that blocked adducts deblock at 240°C, causing the regeneration of TDI, and causing the diisocyanates to react with polyols of different mol. weights, forming polyurethanes. The characterization of the polyurethanes was performed by IR spectroscopy, NMR spectroscopy, thermogravimetric anal., differential scanning calorimetry and a contact angle study. In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Electric Literature of C9H7BrN2).

3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9) 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. 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. Electric Literature of C9H7BrN2

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

Pyrazoles. I. Ionization constants and ultraviolet spectra of 4-nitropyrazoles was written by Habraken, Clarisse L.;Van Woerkom, P. C. M.;De Wind, H. W.;Kallenberg, C. G. M.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas in 1966.HPLC of Formula: 5334-39-4 This article mentions the following:

Uv spectral data for 3(5)-methyl-4-nitropyrazole, 3,5-dimethyl-4-nitropyrazole, 1-methyl-4-nitropyrazole, and 1,3,-5-trimethyl-4-nitropyrazole, and ionization constants for the 1st 2 compounds are tabulated. The data indicate the absence of a steric effect of ortho-methyl groups in 4-nitropyrazoles. The findings corroborate the investigations of Ehrlich (CA 55, 2237f). In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4HPLC of Formula: 5334-39-4).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) 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 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.HPLC of Formula: 5334-39-4

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

Synthesis and antimicrobial activity of 2-(1H-pyrazol-4-yl)-1H-benzo[d]imidazole derivatives was written by Bhavanarushi, S.;Gandu, Bharath;Gangagnirao, A.;Vatsala, Rani J.. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2014.Recommanded Product: 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one This article mentions the following:

A series of novel 2-(1H-pyrazol-4-yl)-1H-benzo[d]imidazole derivatives were prepared and tested in vitro for their antimicrobial activity against three gram pos. bacteria like Bacillus licheniformis, Bacillus subtilis and Staphylococcus aureus three Gram neg. bacteria like Escherichia coli, Klebsiella pneumonia and Pseudomonas aeruginosa and four fungal strains like Aspergillus niger, Candida albicans, Fusarium oxysporum and Fusarium solani. The min. inhibitory concentrations (MICs) of some of the synthesized compounds showed high antibacterial and antifungal activities at low concentrations (6.25-200 μg/mL), with respect to reference drug. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Recommanded Product: 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one).

3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. 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.Recommanded Product: 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one

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

Liquefaction of giant fennel (Ferula orientalis L.) in supercritical organic solvents: Effects of liquefaction parameters on product yields and character was written by Aysu, Tevfik;Kucuk, Mehmet Masuk. And the article was included in Journal of Supercritical Fluids in 2013.Electric Literature of C5H9N3 This article mentions the following:

Ferula orientalis L. stalks were liquefied in an autoclave in supercritical organic solvents (methanol, ethanol, 2-propanol, acetone and 2-butanol) with (NaOH, Na₂CO₃, ZnCl₂) and without catalyst at five different temperatures ranging from 240°C to 320°C. The amounts of solid (unconverted raw material), liquid (bio-oil) and gas produced, as well as the composition of the resulting liquid phase, were determined The effects of various parameters such as temperature, solvent, catalyst and ratio of catalyst on product yields were investigated. The results showed that conversion highly depends on the temperature and catalyst. The highest bio-oil yield (53.97%) was obtained using acetone with 10% zinc chloride at 300°C. The liquid products were extracted with benzene and di-Et ether. Some of selected liquid products (bio-oils) were analyzed by elemental, FT-IR and GC-MS. 126 different compounds were identified by GC-MS in the liquid products obtained in ethanol at 300°C. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Electric Literature of C5H9N3).

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 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 C5H9N3

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

Versatile synthesis of 6-alkyl(aryl)-1H-pyrazolo[3,4-d]pyrimidin-4[5H]-ones was written by Reddy, K. Hemender;Reddy, A. Panduranga;Veeranagaiah, V.. And the article was included in Indian Journal of Chemistry in 1992.Computed Properties of C5H8N4O This article mentions the following:

Condensation of 5-amino-1H-pyrazole-4-carboxamide (I, R = H) with various aromatic aldehydes furnishes 6-substituted 1H-pyrazole[3,4-d]pyrimidin-4(5H)-ones II (R¹ = Ph, substituted Ph) via the intermediate 5-(N-arylideneamino)pyrazole-4-carboxamides. II were also synthesized by the reaction of I (R = H) with aromatic carboxylic acids in polyphosphoric acid (PPA) or polyphosphate ester (PPE). Similar treatment of I (R = Ph, Me) with aromatic aldehydes and aromatic carboxylic acids gives exclusively 6-substituted 1-methyl/phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-ones. The title compounds have were also synthesized by the reaction of I with arylideneanilines. In the experiment, the researchers used many compounds, for example, 5-Amino-1-methyl-1H-pyrazole-4-carboxamide (cas: 18213-75-7Computed Properties of C5H8N4O).

5-Amino-1-methyl-1H-pyrazole-4-carboxamide (cas: 18213-75-7) 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 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.Computed Properties of C5H8N4O

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

Compounds containing the trifluoromethyl group was written by Gilman, H.;Tolman, L.;Yeoman, F.;Woods, L. A.;Shirley, D. A.;Avakian, S.. And the article was included in Journal of the American Chemical Society in 1946.Formula: C4H3F3N2O This article mentions the following:

The following compounds were prepared as possible antimalarials. Of the compounds tested only m-(trifluoromethyl)benzenearsonic acid (I) showed activity but the specific contribution of the F₃C group to such action is uncertain. m-F₃CC₆H₄N₂Cl (0.0163 mole), added to a cold solution of 0.0163 mole of 2-hydroxydibenzofuran in KOH (temperature below 5°) with stirring for 30 min., give 46-50% of 1-(m-trifluoromethylphenylazo)-2-hydroxydibenzofuran, red, m. 173-4°; 2,8-dihydroxydibenzofuran gives 15-20% of the 2,5-di-HO derivative, orange-brown, m. 256-7°. m-F₃CC₅H₄Br (Simons and Ramler, C.A. 37, 2341.8) has n_D²⁰ 1.4749, d₂₇²⁹ 1.606 (55% yield); the Grignard reagent yields 52-9% of m-(trifluoromethyl)benzaldehyde (II), b₁₀ 64-6°, n_D²⁰ 1.4660, d₂₇²⁹ 1.300; 2,4-dinitrophenylhydrazone, yellow, m. 259-60°. II (5.48 g.) and 5.3 g. m-F₃CC₆H₄NH₂ in 50 cc. C₆H₆, refluxed 5 hrs., give 62% of N-(m-trifluoromethylbenzylidene)-m-(trifluoromethyl)aniline, m. 50-1°. II yields 65% of an oxime, b₁₂ 102-4°, n_D²⁰ 1.5128, d₂₇²⁹ 1.305. p-H₂NC₆H₄NHAc (25 g.) and 19 g. (CH₂Ac)₂, heated on the steam bath for 1 hr., give 73% of N-(p-acetamidophenyl)-2,5-dimethylpyrrole, m. 207-8°. 4-Dibenzofuraldehyde yields a 2,4-dinitrophenylhydrazone, yellow, m. 301-2°. II (0.95 g.) and 1 g. 4-aminodibenzofuran in C₆H₆, refluxed 1 hr. and the residual red oil heated at 120-30° for 1 hr., give 29% of 4-(m-trifluoromethylbenzylideneamino)dibenzofuran, m. 81-3°. m-F₃CC₆H₄NH₂ (10 g.), 11.5 g. Et₂N(CH₂)₃Cl, and a trace of Cu, heated 5 hrs. at 135-40°, give 27% of m-(3-diethylaminopropylamino)(trifluoromethyl)benzene, light yellow, b₂₃ 171-5°. m- F₃CC₆H₄N₂Cl yields 51% of I, m. 137-8°. 3,6-H₂N(O₂N)C₆H₃CF₃ (Rouche, C.A. 22, 2149) (41 g.), 29 g. H₃AsO₃, and 53 g. C₃H₅(OH)₃, added to 56 g. concentrated H₂SO₄, stirred 2 hrs., and refluxed 2 hrs., give 56% of 6-nitro-7-(trifluoromethyl)quinoline, m. 164-5°; reduction with SnCl₂-concentrated HCl gives 92% of the 6-NH₂ derivative (III), m. 154-5°. III (5 g.) and (CH₂Ac)₂ in 10 cc. EtOH and 1 drop concentrated HCl, refluxed 22 hrs., give 46% of 6-(2,5-dimethylpyrryl)-7-(trifluoromethyl)quinoline, b₁ 135-8°, m. 86-7°. F₃CCH₂COCH₂CO₂Et (10 g.) and 2.6 cc. N₂H₄.H₂O in 20 cc. hot H₂O give 46.3% of 3-trifluoromethyl-5-pyrazolone, m. 208.5-9.2°. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Formula: C4H3F3N2O).

3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0) 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. 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. Formula: C4H3F3N2O

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

Heterocycle synthesis through reactions of nucleophiles with acrylonitriles. 12. A new route for the synthesis of pyrano[3,2-d]pyrimidines and pyrano[2,3-c]pyrazoles was written by Abdel-Latif, Fathy Fahim. And the article was included in Indian Journal of Chemistry in 1991.HPLC of Formula: 51395-52-9 This article mentions the following:

A new route for the synthesis of pyranopyrimidines I (X = O, S; Ar = Ph, 2-furyl, 2-thienyl, 4-pyridyl) through the reaction of barbituric acid or thiobarbituric acid with ArCH:CRR¹ (II; R = CN; R¹ = CO₂Et) is reported. A similar reaction of II (R = R¹ = CN) gave ylidenes III. The reaction of bromomethylpyrazolinone IV with II (Ar = 2-thienyl; R = R¹ = CN) gave pyranopyrazole V. 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. 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 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.HPLC of Formula: 51395-52-9

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