Tag: 100-200

Synthesis of thienopyrimidine-pyrazolo[3,4-b]pyridine hybrids was written by Park, Jae Woo;Song, Yang-Heon. And the article was included in Heterocyclic Communications in 2017.Electric Literature of C8H8N2S This article mentions the following:

New hybrid compounds, thienopyrimidinyl-1H-pyrazolo[3,4-b]pyridines I [R¹ = R² = H; R¹R² = (CH₂)₃, (CH₂)₄; R³ = 4-Me, 4-MeO, 4-Br] and II were efficiently synthesized by the three-component reaction of 3-phenyl-1-(thienopyrimidin-4-yl)-1H-pyrazol-5-amines, benzoylacetonitrile and an aromatic aldehydes in the presence of FeCl₃ on basic alumina. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Electric Literature of C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Electric Literature of C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Physicochemical Investigation on the Complexes of Co(II), Ni(II) and Cu(II) with Aminocyclodiphosph(V)azane Derivative was written by Abd-Ellah, I. M.;El-Sayed, B. A.;El-Nawawy, M. A.;Alaghaz, A. M. A.. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2002.SDS of cas: 70291-62-2 This article mentions the following:

Co(II), Ni(II), and Cu(II) form 2:1 complexes with aminocyclodiphosph(V)azane derivative The complexes have been investigated in solution by the spectrophotometric molar ratio and conductometric methods. The ligand and its complexes have been isolated in solid state and characterized on the basis of microanal., IR, electronic, magnetic moment, ¹H NMR and mass spectral data. The cobalt and nickel complexes were assigned to be in tetrahedral structure while the copper complex is assigned to be in square planar. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2SDS of cas: 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. SDS of cas: 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pot, Atom, Step Economic (PASE) Approach towards (Aza)-2,2′-Bipyridines: Synthesis and Photophysical Studies was written by Khasanov, Albert F.;Kopchuk, Dmitry S.;Kim, Grigory A.;Slepukhin, Pavel A.;Kovalev, Igor S.;Santra, Sougata;Zyryanov, Grigory V.;Majee, Adinath;Chupakhin, Oleg N.;Charushin, Valery N.. And the article was included in ChemistrySelect in 2018.Product Details of 36057-44-0 This article mentions the following:

An efficient approach towards α-unsubstituted-2,2′-bipyridines, their aza-analogs and 3,6-disubstituted-1,2,4-triazine precursors is reported via pot, atom, step economic (PASE) process starting from isonitrosoacetophenone hydrazone and readily available hetero-arylnitriles. The crystal structures of three key compounds were confirmed by means of X-ray diffraction anal.In addition the photophys. properties of the new (aza)-2,2′-pyridines were studied. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Product Details of 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. 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 36057-44-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of substituted 2-alkylquinolines by visible-light photoredox catalysis was written by Mei, Yousheng;Liu, Jie;Wang, Lei;Li, Pinhua. And the article was included in Organic & Biomolecular Chemistry in 2020.Electric Literature of C8H8N2 This article mentions the following:

The condensation of anilines RNH₂ (R = 2-methyl-4-chlorophenyl, 4-chlorophenyl, 2-methoxyphenyl, etc.) and alkenyl ethers such as ethoxyethene, (E)-1-ethoxyprop-1-ene, (E)-1-ethoxybut-1-ene has been demonstrated by employing visible-light photoredox catalysis. The resulting method enables the synthesis of substituted 2-alkylquinolines I [R¹ = Me, Et, Pr; R² = H, Me, Et; R³ = H, I, Br, etc.; R⁴ = CN, COOMe, Me, etc.; R⁵ = H, Br, Me, etc.], II (R⁶ = H, CF₃, Et, OMe; R⁷ = H, Cl, Br) under mild and simple conditions with good substrate scope and high yields. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Electric Literature of C8H8N2).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. 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.Electric Literature of C8H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and biological evaluation of novel pyrazolo[1,5-a]pyrimidines: Discovery of a selective inhibitor of JAK1 JH2 pseudokinase and VPS34 was written by Singleton, Justin D.;Dass, Reuben;Neubert, Nathaniel R.;Smith, Rachel M.;Webber, Zak;Hansen, Marc D. H.;Peterson, Matt A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2020.COA of Formula: C8H5Cl2N This article mentions the following:

A series of novel 3,6-di-substituted or 3-substituted pyrazolo[1,5-a]pyrimidines were prepared via a microwave-assisted approach that generated a broad array of derivatives in good yields (20-93%, ave. = 59%). The straightforward synthesis involved sequential treatment of com.-available acetonitrile derivatives with DMF-dimethylacetal (120°C, 20 min), followed by treatment with NH₂NH₂·HBr (120°C, 20 min), and 1,1,3,3-tetramethoxypropane or 2-aryl-substituted malondialdehdyes (120°C, 20 min). Compounds were screened for antimitotic activities against MCF7 breast cancer and/or A2780 ovarian cancer cell lines in vitro. The most active compounds exhibited EC₅₀ values ranging from 0.5 to 4.3μM, with the 3-(4-(trifluoromethyl)phenyl)-6-[4-(2-(piperidin-1-yl)ethoxy)]phenyl analog and the 3-(2-fluorophenyl)-6-[4-(2-(4-methylpiperizin-1-yl)ethoxy)]phenyl analog being two to three fold more active than Compound C (Dorsomorphin) in A2780 and MCF7 assays, resp. Importantly, a monosubstituted 3-(benzothiazol-2-yl) derivative was equipotent with the more synthetically challenging 3,6-disubstituted derivatives, and exhibited a promising and unique selectivity profile when screened against a panel consisting of 403 protein kinases (Kinomescan selectivity score = 0.005, K_d = 0.55 ± 0.055μM and 0.410 ± 0.20μM for JAK1 JH2 pseudokinase and VPS34, resp.). In the experiment, the researchers used many compounds, for example, 2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9COA of Formula: C8H5Cl2N).

2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).COA of Formula: C8H5Cl2N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Crown cation complex effects. 10. Potassium tert-butoxide mediated penultimate oxidative hydrolysis of nitriles was written by DiBiase, Stephen A.;Wolak, Raymond P. Jr.;Dishong, Dennis M.;Gokel, George W.. And the article was included in Journal of Organic Chemistry in 1980.Electric Literature of C8H13N This article mentions the following:

The failure of phase-transfer catalysis to improve either the yield or rapidity of basic nitrile hydrolysis is due, in part, to the poor solubility of quaternary ammonium hydroxides in nonpolar solutions An alternative hydrolysis method which involves KOCMe₃ mediated oxidative cleavage of the nitrile with loss of the cyano carbon is presented. The isolated yields range from 21-93% and are highest for long-chain aliphatic nitriles such as cyanohexadecane. Other compounds that underwent oxidative hydrolysis were PhCH₂CN, cyclohexaneacetonitrile, and cyclododecanecarbonitrile. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Electric Literature of C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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.Electric Literature of C8H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

9-Amino-1,2,3,4-tetrahydroacridin-1-ols. Synthesis and evaluation as potential Alzheimer’s disease therapeutics was written by Shutske, Gregory M.;Pierrat, Frank A.;Kapples, Kevin J.;Cornfeldt, Michael L.;Szewczak, Mark R.;Huger, Francis P.;Bores, Gina M.;Haroutunian, Vahram;Davis, Kenneth L.. And the article was included in Journal of Medicinal Chemistry in 1989.Safety of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

The synthesis of a series of 9-amino-1,2,3,4-tetrahydroacridin-1-ols is reported. These compounds are related to tacrine. They inhibit acetylcholinesterase in vitro and are active in a model that may be predictive of activity in Alzheimer’s disease; the scopolamine-induced impairment of 24-h memory of a passive dark-avoidance paradigm in mice. Two compounds, (±)-9-amino-1,2,3,4-tetrahydroacridin-1-ol maleate (HP-029) and (±)-9-(benzylamino)-1,2,3,4-tetrahydroacridin-1-ol maleate (HP-128), were also active in reversing the deficit in 72-h retention of a (1-trial dark-avoidance task in rats, induced by ibotenic acid lesions in the nucleus basalis magnocellularis. In addition, HP-128 showed potent in vitro inhibition of the uptake of radiolabeled noradrenaline and dopamine (IC₅₀ = 0.070 μM and 0.30 μM, resp.). HP-029 and HP-128, which showed less acute toxicity in both rats and mice than tacrine, are in phase II and phase I clin. trials, resp., for Alzheimer’s disease. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Safety of 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Safety of 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Potent and highly selective DP1 antagonists with 2,3,4,9-tetrahydro-1H-carbazole as pharmacophore was written by Li, Lianhai;Beaulieu, Christian;Carriere, Marie-Claude;Denis, Danielle;Greig, Gillian;Guay, Daniel;O’Neill, Gary;Zamboni, Robert;Wang, Zhaoyin. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C9H9NO This article mentions the following:

It was discovered that the introduction of a Me group to the benzylic position of the N-benzyl group in lead compound I has a dramatic effect on improving the binding selectivity of this ligand for the prostanoid receptors DP1 (receptor for prostaglandin D₂) as compared to TP (receptor for thromboxane A₂). Based on this discovery, a series of potent and highly selective DP1 antagonists have been synthesized. Among them, compound II was identified as a highly selective DP1 antagonist with excellent overall properties. It has a K_i of 0.43 nM to DP1 in binding assay and an IC₅₀ of 2.5 nM in the DP1 functional assay. Its selectivity for DP1 over TP (the most potent receptor after DP1) exceeds 750-fold based on both binding and functional assays. These properties make II a very potent and highly selective DP1 receptor antagonist suitable for investigating the biol. functions of DP1 in normal physiol. and models of disease. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Formula: C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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.Formula: C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly Enantioselective Hydrosilylation of Ketones Catalyzed by a Chiral Oxazaborolidinium Ion was written by Kang, Byung Chul;Shin, Sung Ho;Yun, Jaesook;Ryu, Do Hyun. And the article was included in Organic Letters in 2017.Application In Synthesis of (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

A highly enantioselective hydrosilylation of ketones was developed for the synthesis of a variety of chiral secondary alcs. In the presence of a chiral oxazaborolidinium ion (COBI) catalyst, the reaction proceeded with good yields (up to 99%) with excellent enantioselectivities (up to 99% ee). In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Application In Synthesis of (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application In Synthesis of (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Asymmetric transfer hydrogenation of ketones catalyzed by rhenium complexes with chiral ferrocenylphosphane ligands was written by Mejia, Esteban;Aardoom, Raphael;Togni, Antonio. And the article was included in European Journal of Inorganic Chemistry in 2012.Electric Literature of C9H9NO This article mentions the following:

A series of new rhenium complexes containing chiral ferrocenyldiphosphine ligands, I (R = Ph, Cy; R¹ = Cy, 1-adamantyl, 3,5-(CF₃)₂C₆H₃, 3,5-Me₂C₆H₃) of the Josiphos family, starting from com. available rhenium sources. These new Re^V oxido and nitrido complexes, several of which have been characterized by x-ray crystallog., are air- and moisture-stable and are active catalysts in the asym. transfer hydrogenation of ketones using 2-propanol as the hydrogen source in the presence of substoichiometric amounts of triethylamine (TEA). The reaction proceeds cleanly with good to excellent yields (50-99 %) but with moderate enantioselectivity (up to 58 % ee). A mechanism not involving hydridic species is proposed. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Electric Literature of C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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.Electric Literature of C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts