Tag: 100-200

Cyano-substituted 5-thiabicyclo[2.1.0]pent-2-enes: reactions and relevance to cyanothiophene phototranspositions was written by Barltrop, John A.;Day, A. Colin;Irving, Edward. And the article was included in Journal of the Chemical Society, Chemical Communications in 1979.Quality Control of 3-Methylthiophene-2-carbonitrile This article mentions the following:

The title thiabicyclopentenes were detected by NMR as intermediates in the photorearrangements of cyanothiophenes. Thiabicyclopentene I was obtained (6%) on irradiation of 3-cyano-2-methyl- or -4-methylthiophene in cyclohexane at ∼34°. Aromatization and rearrangement by S walk of I, which occur photochem. and thermally, and its Diels-Alder reactions with furan and 2,5-diphenyl-3,4-benzofuran were studied. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Quality Control of 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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).Quality Control of 3-Methylthiophene-2-carbonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of Structure-Based Drug Design and Parallel Chemistry to Identify Selective, Brain Penetrant, In Vivo Active Phosphodiesterase 9A Inhibitors was written by Claffey, Michelle M.;Helal, Christopher J.;Verhoest, Patrick R.;Kang, Zhijun;Bundesmann, Mark W.;Hou, Xinjun;Lui, Shenping;Kleiman, Robin J.;Vanase-Frawley, Michelle;Schmidt, Anne W.;Menniti, Frank;Schmidt, Christopher J.;Hoffman, William E.;Hajos, Mihaly;McDowell, Laura;O’Connor, Rebecca E.;MacDougall-Murphy, Mary;Fonseca, Kari R.;Becker, Stacey L.;Nelson, Frederick R.;Liras, Spiros. And the article was included in Journal of Medicinal Chemistry in 2012.Recommanded Product: 2-Fluoro-5-hydroxybenzenecarbonitrile This article mentions the following:

Phosphodiesterase 9A inhibitors have shown activity in preclin. models of cognition with potential application as novel therapies for treating Alzheimer’s disease. Our clin. candidate, PF-04447943 (2), demonstrated acceptable CNS permeability in rats with modest asymmetry between central and peripheral compartments (free brain/free plasma = 0.32; CSF/free plasma = 0.19) yet had physicochem. properties outside the range associated with traditional CNS drugs. To address the potential risk of restricted CNS penetration with 2 in human clin. trials, we sought to identify a preclin. candidate with no asymmetry in rat brain penetration and that could advance into development. Merging the medicinal chem. strategies of structure-based design with parallel chem., a novel series of PDE9A inhibitors was identified that showed improved selectivity over PDE1C. Optimization afforded preclin. candidate 19 that demonstrated free brain/free plasma ≥1 in rat and reduced microsomal clearance along with the ability to increase cyclic guanosine monophosphosphate levels in rat CSF. In the experiment, the researchers used many compounds, for example, 2-Fluoro-5-hydroxybenzenecarbonitrile (cas: 104798-53-0Recommanded Product: 2-Fluoro-5-hydroxybenzenecarbonitrile).

2-Fluoro-5-hydroxybenzenecarbonitrile (cas: 104798-53-0) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Recommanded Product: 2-Fluoro-5-hydroxybenzenecarbonitrile

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Nitrile – Wikipedia,
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Selectively Oxidative Thiolysis of Nitriles into Primary Thioamides and Insecticidal Application was written by Huang, Zhuo-Bin;Guo, Xue-Ying;Huang, Zi-Hao;Li, Ming-Hua;Dong, Shou-Cheng;Tang, Ri-Yuan. And the article was included in Asian Journal of Organic Chemistry in 2020.Product Details of 36057-44-0 This article mentions the following:

Primary thioamides were useful building blocks for drug and insecticide development, therefore an environmentally benign synthesis of primary thioamides was desired. An oxidative thiolysis for the selective transformation of nitriles into primary thioamides using elemental sulfur or thiuram in the presence of K₂S₂O₈ in DMF/H₂O was discussed. This practical method enables access to a wide range of synthetically and pharmaceutically useful primary thioamides. Advantages of this reaction include transition-metal-free and base-free reaction conditions, use of an environmentally benign solvent (DMF/H₂O) system, the use of non-toxic elemental sulfur or thiuram as the sulfur sources, and good functional groups tolerances with excellent selectivity. Furthermore, the insecticide Fipronil was also converted to the corresponding thioamide and maintains excellent bioactivity against P. xylostella. The LC₅₀ value of Fipronil thioamide was 1.25 mg/L. 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 carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Product Details of 36057-44-0

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A general method for the direct α-arylation of nitriles with aryl chlorides was written by You, Jingsong;Verkade, John G.. And the article was included in Angewandte Chemie, International Edition in 2003.SDS of cas: 5351-07-5 This article mentions the following:

The long-standing challenge of developing a general method for the title methodol. is met for a broad range of aryl chlorides through the use of bicyclic P(iBuNCH₂CH₂)₃N as bulky electron-rich ligand for palladium. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5SDS of cas: 5351-07-5).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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 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.SDS of cas: 5351-07-5

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Quinazolinones from o-Aminobenzonitriles by One-Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex was written by Zhao, Wei;Liu, Pengcheng;Li, Feng. And the article was included in ChemCatChem in 2016.Category: nitriles-buliding-blocks This article mentions the following:

A new strategy for the direct synthesis of quinazolinones from o-aminobenzonitriles was proposed and accomplished. In the presence of [Cp*IrCl₂]₂ (Cp*=pentamethylcyclopentadienyl), a variety of desirable products was obtained easily through the one-pot sequential selective hydration/condensation/acceptorless dehydrogenation. This protocol was highly attractive because it used readily available starting materials, has a high atom efficiency, good to excellent yields, and minimal consumption of chems. and energy. Notably, this research exhibited new potential for the development of transition-metal-catalyzed one-pot sequential reactions that involve acceptorless dehydrogenation. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Category: nitriles-buliding-blocks).

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. 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. Category: nitriles-buliding-blocks

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Design, characterisation and anticonvulsant evaluation of thienopyrimidinone derivatives synthesised by green chemistry was written by Raju, Gollapalli Naga;Sucharitha, Nallamothu;Navya, Nagandla;Nadendla, Rama Rao. And the article was included in Journal of Chemical and Pharmaceutical Research in 2017.COA of Formula: C8H8N2S This article mentions the following:

The synthesis and biol. evaluation of some novel thieno[2,3-d]pyrimidin-4(3H)one derivatives was aimed at creating a new scaffold. Considering the previous articles activity profile of thienopyrimidinone derivatives, fifteen new substituted thieno[2,3-d]pyrimidin-4(3H)one derivatives were synthesized by reacting different 2-amino-4,5-substituted thiophene-3-carbonitriles with appropriate aliphatic carboxylic acids in presence of phosphoryl trihloride and alumina by conventional synthesis as well as microwave assisted route. Structural characterizations of all the synthesized compounds were performed by using spectral and elemental anal. All the synthesized compounds were evaluated for their antimicrobial and anticonvulsant activities by using disk diffusion method and maximal electroshock induced seizures (MES) method. It was found that the compounds possessed potent antimicrobial and anticonvulsant activities. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2COA of Formula: 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.COA of Formula: C8H8N2S

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2-Substituted 8,9-cycloalkathieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones was written by Chernyuk, O. M.;Tolmachova, V. S.;Vovk, M. V.. And the article was included in Ukrainskii Khimicheskii Zhurnal (Russian Edition) in 2009.Recommanded Product: 70291-62-2 This article mentions the following:

A series of cycloalkane-fused thieno[3.2-e][1,2,4]triazolo[1,5-c]pyrimidinones I [R¹R² = (CH₂)₃, (CH₂)₄, CH₂CHMeCH₂CH₂, (CH₂)₅; R³ = Ph, 4-FC₆H₄, 2-furyl, 3-pyridyl, etc.] was synthesized by condensation of N-(cyanothienyl) carbamates II with carboxylic acids hydrazides R³CONHNH₂. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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.Recommanded Product: 70291-62-2

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Nitrile – Wikipedia,
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Radical Trifluoromethoxylation of Arenes Triggered by a Visible-Light-Mediated N-O Bond Redox Fragmentation was written by Jelier, Benson J.;Tripet, Pascal F.;Pietrasiak, Ewa;Franzoni, Ivan;Jeschke, Gunnar;Togni, Antonio. And the article was included in Angewandte Chemie, International Edition in 2018.Application of 63968-85-4 This article mentions the following:

A simple trifluoromethoxylation method enables non-directed functionalization of C-H bonds on a range of substrates, providing access to aryl trifluoromethyl ethers. This light-driven process is distinctly different from conventional procedures and occurs through an OCF₃ radical mechanism mediated by a photoredox catalyst, which triggers an N-O bond fragmentation. The pyridinium-based trifluoromethoxylation reagent is bench-stable and provides access to synthetic diversity in lead compounds in an operationally simple manner. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4Application of 63968-85-4).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) 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.Application of 63968-85-4

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Optimization of 5-(2,6-dichlorophenyl)-3-hydroxy-2-mercaptocyclohex-2-enones as potent inhibitors of human lactate dehydrogenase was written by Labadie, Sharada;Dragovich, Peter S.;Chen, Jinhua;Fauber, Benjamin P.;Boggs, Jason;Corson, Laura B.;Ding, Charles Z.;Eigenbrot, Charles;Ge, HongXiu;Ho, Qunh;Lai, Kwong Wah;Ma, Shuguang;Malek, Shiva;Peterson, David;Purkey, Hans E.;Robarge, Kirk;Salphati, Laurent;Sideris, Steven;Ultsch, Mark;VanderPorten, Erica;Wei, BinQing;Xu, Qing;Yen, Ivana;Yue, Qin;Zhang, Huihui;Zhang, Xuying;Zhou, Aihe. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Quality Control of 2-Bromo-4-hydroxybenzonitrile This article mentions the following:

Optimization of 5-(2,6-dichlorophenyl)-3-hydroxy-2-mercaptocyclohex-2-enone using structure-based design strategies resulted in inhibitors with considerable improvement in biochem. potency against human lactate dehydrogenase A (LDHA). These potent inhibitors were typically selective for LDHA over LDHB isoform (4-10 fold) and other structurally related malate dehydrogenases, MDH1 and MDH2 (>500 fold). An X-ray crystal structure of enzymically most potent mol. bound to LDHA revealed two addnl. interactions associated with enhanced biochem. potency. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Quality Control of 2-Bromo-4-hydroxybenzonitrile).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Quality Control of 2-Bromo-4-hydroxybenzonitrile

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Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N- Mesyl-, and N-Tosyldibenzothiophene Sulfilimines was written by Desikan, Vasumathi;Liu, Yonglin;Toscano, John P.;Jenks, William S.. And the article was included in Journal of Organic Chemistry in 2008.Reference of 4435-14-7 This article mentions the following:

Time-resolved IR (TRIR) spectroscopy, product studies, and computational methods were applied to the photolysis of sulfilimines derived from dibenzothiophene that were expected to release acetylnitrene, trifluoroacetylnitrene, mesylnitrene, and tosylnitrene. All three methods provided results for acetylnitrene consistent with literature precedent and analogous experiments with the benzoylnitrene precursor, i.e., that the ground-state multiplicity is singlet. In contrast, product studies clearly indicate triplet reactivity for trifluoroacetylnitrene, though TRIR experiments were more ambiguous. Product studies suggest that these sulfilimines are superior sources for sulfonylnitrenes, which have triplet grounds states, to the corresponding azides, and computational studies shed light on the electronic structure of the nitrenes. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Reference of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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.Reference of 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts