Tag: 100-200

A new synthesis of aryl substituted quinazolin-4(1H)-ones was written by Roth, Gary A.;Tai, Jimmy J.. And the article was included in Journal of Heterocyclic Chemistry in 1996.Product Details of 53312-77-9 This article mentions the following:

Treatment of a variety of substituted 2-aminobenzonitriles I (R¹ = H, 3-F, R² = 3-Me, 5-NO₂, 5-OMe, 3-F, 3-Cl, 5-Cl, 6-Cl) with formic acid under strong acid catalysis provides the corresponding quinazolin-4(1H)-ones II in good yield. A potential reaction pathway is described. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Product Details of 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Product Details of 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Evaluation of Novel Synthetic Methods for the Preparation of the Sodium Channel Inhibitor, GW273225X was written by Walker, Matthew D.;Albinson, F. David;Clark, Hugh F.;Clark, Stacy;Henley, Nicholas P.;Horan, Richard A. J.;Jones, Chris W.;Wade, Charles E.;Ward, Richard A.. And the article was included in Organic Process Research & Development in 2014.Product Details of 3218-45-9 This article mentions the following:

The evaluation of efficient synthetic methods for the preparation of (R)-2,4-diamino-5-(2,3-dichlorophenyl)-6-fluoromethylpyrimidine (GW273225X, I), is described. The initial synthesis using Et fluoroacetate was evaluated against three alternative routes using either nucleophilic fluorination, electrophilic fluorination, or sodium fluoroacetate. In the experiment, the researchers used many compounds, for example, 2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9Product Details of 3218-45-9).

2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Product Details of 3218-45-9

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Palladium Catalyzed Distal meta-C-H Functionalization of Arylacetic Acid Derivatives was written by Srinivas, Dasari;Satyanarayana, Gedu. And the article was included in Organic Letters in 2021.Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile This article mentions the following:

Herein, meta-C-H olefination of phenylacetic acid derivatives I [R¹ = R² = Me, Et; R¹ = H, R² = Me; R¹R² = (CH₂)₄; R³ = H, 3-Me, 4-MeO, 4-Br, 3,4-Cl₂, etc.] with alkenes R⁴CH:CHR⁵ (R⁴ = H, R⁵ = MeO₂C, EtO₂C, Me₂NCO, MeSO₂, 4-O₂NC₆H₄, etc.; R⁴ = R⁵ = EtO₂C; etc.) for the synthesis of arylacrylates and analogs II by tethering with a simple nitrile-based template through palladium catalysis has been presented. Notably, the versatility of the method has been evaluated with a wide range of phenylacetic acid derivatives for accomplishing the meta-olefination products in fair to excellent yields with outstanding selectivities under milder conditions. Significantly, the present strategy was successfully exemplified for the synthesis of drugs/natural product analogs, such as naproxen, ibuprofen, paracetamol, and cholesterol. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of dendramines, dendramides and their new application in the oil industry was written by Katritzky, Alan R.;Yang, Baozhen;Tack, Robert D.. And the article was included in Journal of the Chinese Chemical Society (Taipei) in 1997.Formula: C9H12N4 This article mentions the following:

A series of dendramines and dendramides have been synthesized and some of their “anti-freeze” properties in diesel fuels have been tested, showing that these compounds are good oil additives for reducing the wax-like crystals which block the fuel filters. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Formula: C9H12N4).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Formula: C9H12N4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2,4,6-Triaminopyrimidine as a Novel Hinge Binder in a Series of PI3Kδ Selective Inhibitors was written by Patel, Leena;Chandrasekhar, Jayaraman;Evarts, Jerry;Haran, Aaron C.;Ip, Carmen;Kaplan, Joshua A.;Kim, Musong;Koditek, David;Lad, Latesh;Lepist, Eve-Irene;McGrath, Mary E.;Novikov, Nikolai;Perreault, Stephane;Puri, Kamal D.;Somoza, John R.;Steiner, Bart H.;Stevens, Kirk L.;Therrien, Joseph;Treiberg, Jennifer;Villasenor, Armando G.;Yeung, Arthur;Phillips, Gary. And the article was included in Journal of Medicinal Chemistry in 2016.Application of 60025-09-4 This article mentions the following:

Inhibition of phosphoinositide 3-kinase δ (PI3Kδ) is an appealing target for several hematol. malignancies and inflammatory diseases. Herein, we describe the discovery and optimization of a series of propeller shaped PI3Kδ inhibitors comprising a novel triaminopyrimidine hinge binder. Combinations of electronic and structural strategies were employed to mitigate aldehyde oxidase mediated metabolism This medicinal chem. effort culminated in the identification of 52, a potent and highly selective inhibitor of PI3Kδ that demonstrates efficacy in a rat model of arthritis. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Application of 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Application of 60025-09-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Conformational preferences of some substituted methyl groups in cyclohexanes as studies by carbon-13 nuclear magnetic resonance was written by Kitching, William;Olszowy, Henry;Adcock, William. And the article was included in Organic Magnetic Resonance in 1981.SDS of cas: 4435-14-7 This article mentions the following:

Low-temperature ¹³C NMR spectra of 80:20 mixtures of the cis and trans isomers of the disubstituted cyclohexanes I (R = Br, cyano, OH, OMe, SiMe₃, SnMe₃, PbMe₃, HgOAc) were recorded. After assignment of signals arising from the trans isomer, the conformational equilibrium of the cis components were determined by anal. of spectral intensities. From these the equilibrium A values of CH₂R (R as before) were calculated using the counter-poise approach. The values were similar to that of Me. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7SDS of cas: 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.SDS of cas: 4435-14-7

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and N-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines was written by Ek, Fredrik;Manner, Sophie;Wistrand, Lars-Goeran;Frejd, Torbjoern. And the article was included in Journal of Organic Chemistry in 2004.Electric Literature of C8H5F3N2 This article mentions the following:

A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddition between a nitrile and (TMS)N₃ followed by an intramol. N-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An exo-methylene group in these new compounds permitted further derivatization. Structural resemblance with substances which possess important pharmacol. properties (e.g., losartan and flumazenil) motivated the synthesis of a series of ketones and a small library of amines. A comparison was made between the pharmacophore of (-)-epibatidine and a low energy conformation of N-methyl-5H-tetrazolo[5,1-a][2]benzazepin-6-amine. The reaction of 2-aminobenzonitrile derivatives with 3-bromo-2-(bromomethyl)-1-propene in the presence of tert-Bu nitrite gave 2-[2-(Bromomethyl)-2-propenyl]benzonitrile derivatives I (R = 5-Cl, 5-Br, 4-NO₂, 5-NO₂, 4-CF₃, 4-Cl-5-Br). Treatment of I with (azido)trimethylsilane in the presence of dibutyltin oxide and sequential ozonization gave 5H-tetrazolo[5,1-a][2]benzazepin-6-ones II (same R). Further reductive amination of II gave tetrazolo[5,1-a][2]benzazepin-6-amines III (same R, R¹ = H, PhCH₂; R¹R¹N = morpholino, etc.). In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Electric Literature of C8H5F3N2).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Electric Literature of C8H5F3N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrochemical Trifluoromethoxylation of (Hetero)aromatics with a Trifluoromethyl Source and Oxygen was written by Ouyang, Yao;Xu, Xiu-Hua;Qing, Feng-Ling. And the article was included in Angewandte Chemie, International Edition in 2022.COA of Formula: C8H4F3NO This article mentions the following:

A conceptually new and operationally simple protocol for the direct C-H trifluoromethoxylation of (hetero)aromatics by the combination of the readily available trifluoromethylating reagent and oxygen under electrochem. reaction conditions was discussed. This reaction proceeded through the initial generation of CF₃ radical followed by conversion to CF₃O radical, addition to (hetero)aromatics and rearomatization. The utility of this electrochem. trifluoromethoxylation was illustrated by the direct incorporation of CF₃O group into a variety of (hetero)aromatics as well as bio-relevant mols. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4COA of Formula: C8H4F3NO).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.COA of Formula: C8H4F3NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Meisenheimer-type adducts from thiophene derivatives. Part 6. A kinetic and thermodynamic study of substituent effects on the formation of some non-gem adducts was written by Arnone, Caterina;Consiglio, Giovanni;Spinelli, Domenico;Dell’Erba, Carlo;Sancassan, Fernando;Terrier, Francois. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1989.Application of 42137-24-6 This article mentions the following:

The rate and equilibrium constants for the formation of the Meisenheimer-type adducts I and II from 4-nitro-2-X- or 2-nitro-4-X-thiophenes and sodium methoxide have been measured at 25° in methanol or methanol-DMSO mixtures The observed stability and reactivity patterns have been interpreted in the light of the hyper-ortho relation in the thiophene ring and the special ability of the nitro group to stabilize effectively the adducts from a para-like position also. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Application of 42137-24-6).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Application of 42137-24-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pyrrolo[1,2-a][1,4]benzodiazepine: A novel class of non-azole anti-dermatophyte anti-fungal agents was written by Meerpoel, Lieven;Van Gestel, Jef;Van Gerven, Frans;Woestenborghs, Filip;Marichal, Patrick;Sipido, Vic;Terence, Gilkerson;Nash, Roger;Corens, David;Richards, Ray D.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2005.HPLC of Formula: 53312-77-9 This article mentions the following:

Broad screening revealed compound I to be a novel anti-fungal agent with high specificity towards dermatophytes. The anti-fungal structure-activity relationship of this novel class of 5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines is described together with its mode of action that appeared to be the inhibition of squalene epoxidase. Preliminary in vivo results of the most active compounds are also reported. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9HPLC of Formula: 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.HPLC of Formula: 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts