Nitriles-buliding-blocks

“On-Water” Palladium-Catalyzed Tandem Cyclization Reaction for the Synthesis of Biologically Relevant 4-Arylquinazolines was written by Yuan, Shuo;Yu, Bin;Liu, Hong-Min. And the article was included in Chemistry – A European Journal in 2019.Safety of 2-Amino-3,5-dibromobenzonitrile This article mentions the following:

The quinazoline scaffold is prevalent in pharmaceutically relevant mols. that show diverse biol. activities. An efficient “on-water” palladium-catalyzed tandem cyclization reaction from com. available arylboronic acids RB(OH)₂ (R = Ph, 3-nitrophenyl, naphthalen-1-yl, etc.) and benzonitriles (E)-2-CN-R¹C₆H₄N=C(R²)N(Me)₂ [R¹ = H, 5-Me, 4,5-(OMe)₂, etc.; R² = H, Me] that enable the rapid access to 4-arylquinazoline scaffolds I [R³ = H, 7-Me, 6,7-(OMe)₂, etc.] in good to excellent yields (45 examples, up to 98% yield) was reported. This protocol has shown good functional group tolerance and broad substrate scope. The reaction was also performed on a gram scale and successfully applied to the synthesis of the highly potent and selective PI3Kδ inhibitor II, showing the practicability and synthetic utility of the protocol. In this reaction, the quinazoline scaffold I is efficiently constructed with the simultaneous formation of one C-C bond and one C-N bond. Collectively, the protocol could serve as an alternative strategy to synthesize biol. important quinazoline scaffolds. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Safety of 2-Amino-3,5-dibromobenzonitrile).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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.Safety of 2-Amino-3,5-dibromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Stable and reusable nanoscale Fe₂O₃-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides was written by Murugesan, Kathiravan;Senthamarai, Thirusangumurugan;Sohail, Manzar;Sharif, Muhammad;Kalevaru, Narayana V.;Jagadeesh, Rajenahally V.. And the article was included in Green Chemistry in 2018.Application In Synthesis of 3-Methylthiophene-2-carbonitrile This article mentions the following:

The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized mols. is of fundamental interest because nitrogen-containing motifs are found in a large number of life science mols., natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O₂ or air was reported. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesize functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Addnl., applying this iron-based protocol, primary amides have also been prepared in a water medium. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Application In Synthesis 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. 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 In Synthesis of 3-Methylthiophene-2-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis, characterization, and SAR of arylated indenoquinoline-based cholinesterase and carbonic anhydrase inhibitors was written by Ekiz, Makbule;Tutar, Ahmet;Oekten, Salih;Buetuen, Burcu;Kocyigit, Uemit M.;Taslimi, Parham;Topcu, Guelacti. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2018.Product Details of 68385-95-5 This article mentions the following:

The authors report the synthesis of bromoindenoquinolines (15a-f) by Friedlander reactions in low yields (13-50%) and the conversion of the corresponding phenyl-substituted indenoquinoline derivatives 16-21 in high yields (80-96%) by Suzuki coupling reactions. To explore the structure-activity relationship (SAR), their inhibition potentials to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase cyctosolic (hCA I and II) enzymes were determined Monophenyl (16-18) indenoquinolines significantly inhibited the AChE and BChE enzymes in ranges of IC₅₀ 37-57 nM and 84-93 nM, resp., compared with their starting materials 15a-c and reference compounds (galanthamine and tacrine). These novel arylated indenoquinoline-based derivatives were effective inhibitors of the BChE, hCA I and II, BChE and AChE enzymes with K_i values in the range of 37±2.04 to 88640±1990 nM for AChE, 120.94±37.06 to 1150.95±304.48 nM for hCA I, 267.58±98.05 to 1568.16±438.67 nM for hCA II, and 84±3.86 to 144120±2910 nM for BChE. As a result, monophenyl indenoquinolines 16-18 may have promising anti-Alzheimer drug potential and 3,8-dibromoindenoquinoline amine (15f) can be novel hCA I and hCA II enzyme inhibitors. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Product Details of 68385-95-5).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Product Details of 68385-95-5

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Lewis acid-base integrated robust metal-organic framework and reconfigurable composite for solvent-free Biginelli condensation and tandem catalysis with size selectivity was written by Seal, N.;Neogi, S.. And the article was included in Materials Today Chemistry in 2022.Safety of 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

Aiming at environmentally benign catalyzes with less energy consumption, reduction in chem. usage and minimization of wastes, metal-organic frameworks (MOFs) combining basic functionality enriched pores and unsaturated metal centers (UMCs) is most promising. Alternatively, astute tuning of channel dimension in these materials can benefit much anticipated size-exclusive catalysis, whereas fabrication of flexible MOF-composite is imperative considering facile applicability over real-life platforms. The pillar-bilayered and hydrolytically robust MOF, built from tri-carboxylate ligand, linear linker and solvent-bound [Cd₃(COO)₆] secondary building unit exhibits N-functionality enriched porous channels and activation-driven generation of open metal sites. Benefiting from unique bifunctional character, the MOF acts as excellent solvent-free catalyst toward one-pot Biginelli reaction and deacetalization-Knoevenagel condensation under mild condition. Both the reactions transpire with broad substrate scope, high recyclability and superior activity to contemporary materials, wherein single-crystal X-ray diffraction is first time applied as product characterization tool. Judiciously designed control experiments validate individual catalytic routes, thereby substantiating the importance of contrasting pore-functionalities at the interface of structure-property synergism. To the best of three-component coupling and acid-base tandem catalysis, substrates with incompatible mol. dimension to that of the twofold interpenetration generated optimized pores exhibit insignificant conversion and demonstrate unprecedented pore-fitting-actuated size selectivity. In view of practically advanced and eco-friendly substrate design, reconfigurable MOF-cotton fiber composite is fabricated via in situ growth, which delivered excellent yields for both these reactions with comparable reusability to that of pristine framework, delineating a paradigm shift to smart, futuristic and green strategy in synergistic catalysis. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Safety of 2-(Anthracen-9-ylmethylene)malononitrile).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. 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.Safety of 2-(Anthracen-9-ylmethylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Anil Synthesis in the Design of Push-Pull Systems. Synthesis of 2- and 4-(4-Styrylphenyl)-substituted Diphenylpyrimidines was written by Harutyunyan, A. A.;Panosyan, H. A.;Safaryan, M. S.;Gukasyan, G. T.;Danagulyan, G. G.. And the article was included in Russian Journal of Organic Chemistry in 2020.Product Details of 5203-15-6 This article mentions the following:

The potential of anil synthesis for the preparation of 2,4,6-triaryl-substituted pyrimidines I (R = H, OMe, i-Pr; R¹ = H; RR¹ = -OCH₂O-) and II (R² = H, isobutoxy) with an extended chain of delocalized π-bonds was studied. The reaction of (E)-3-phenyl-1-arylprop-2-en-1-ones 4-R³ C₆H₄C(O)CH=CHC(O)C₆H₅ (R³ = H, Me) with benzamidine hydrochlorides 4-R²C₆H₄C(NH₂)=NH.HCl in ethanol in the presence of KOH gave pyrimidines III. The synthesized pyrimidines III were reacted with (E)-N-(phenyl- or 2-chlorophenyl)-1-arylmethanimines 4-R-5-R¹C₆H₃CH=N(2-R⁴C₆H₄) (R⁴ = H, 2-Cl) in DMF in the presence of a KOH/LiH mixture to obtain (E)-4,6-diphenyl-2-(4-styrylphenyl)pyrimidines I and (E)-2,6-diphenyl-4-(4-styrylphenyl)pyrimidines II. In the experiment, the researchers used many compounds, for example, 4-iso-Butoxybenzonitrile (cas: 5203-15-6Product Details of 5203-15-6).

4-iso-Butoxybenzonitrile (cas: 5203-15-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Product Details of 5203-15-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design, synthesis and biological evaluation of novel benzothiadiazine derivatives as potent PI3Kδ-selective inhibitors for treating B-cell-mediated malignancies was written by Ma, Xiaodong;Wei, Jun;Wang, Chang;Gu, Dongyan;Hu, Yongzhou;Sheng, Rong. And the article was included in European Journal of Medicinal Chemistry in 2019.Category: nitriles-buliding-blocks This article mentions the following:

A series of 24 benzothiadiazine derivatives I (R¹ = Ph, 4-F-Ph, 3-CF₃-Ph, etc; R² = H, F, Cl; R³ = Me, Et; R⁴ = H, F, Cl), II, III (R⁵ = Ph, 4-F-Ph, 4-OCF₃-Ph, 3-Py; R⁶ = H, F) with structural novelty were designed, synthesized and biol. evaluated as PI3Kδ-selective inhibitors. Structure-activity relationship (SAR) study showed that, compounds I (R¹ = Ph; R² = Cl; R³ = Et; R⁴ = H) and II (R² = Cl; R³ = Me) were identified with single-digit nanomolar IC₅₀ values against PI3Kδ and submicromolar GI₅₀ values against human malignant B-cell line SU-DHL-6. Furthermore, chiral resolution of the key amine intermediate of these two compounds was performed to achieve corresponding enantiomers. Compounds (S)-3-(1-((9H-purin-6-yl)amino)ethyl)-8-chloro-2-phenyl-2Hbenzo[e][1,2,4]thiadiazine 1,1-dioxide(IC₅₀: 4.6 nM) and (S)-4-amino-6-((1-(8-chloro-1,1-dioxido-2-phenyl-2H-benzo[e][1,2,4]thiadiazin-3-yl)ethyl)amino)pyrimidine-5-carbonitrile(IC₅₀: below 0.32 nM) demonstrated comparable and superior PI3Kδ inhibitory activity, resp., to that of idelalisib. Addnl., both the compounds exerted enhanced anti-proliferative activity against the SU-DHL-6 cell line than that of idelalisib and they exhibited excellent PI3Kδ selectivity. The in vivo pharmacokinetic (PK) study revealed that (S)-3-(1-((9H-purin-6-yl)amino)ethyl)-8-chloro-2-phenyl-2Hbenzo[e][1,2,4]thiadiazine 1,1-dioxide displayed good plasma exposure and an acceptable oral bioavailability of 29.2% and can further be developed as a potential therapeutic agent for battling B-cell-mediated malignancies. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Category: nitriles-buliding-blocks).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Facile synthesis and antitumor activity of novel 2-trifluoromethylthieno[2,3-d]pyrimidine derivatives was written by Song, Xin-Jian;Yang, Ping;Gao, Hui;Wang, Yan;Dong, Xing-Gao;Tan, Xiao-Hong. And the article was included in Chinese Chemical Letters in 2014.Application of 70291-62-2 This article mentions the following:

A series of novel 2-trifluoromethylthieno[2,3-d]pyrimidine derivatives were synthesized by a facile three-step procedure that afforded advantages of mild reaction conditions, simple protocol and good yields. The structures of the final compounds were confirmed by IR, NMR, EI-MS, elemental anal., and X-ray diffraction (for compound I). Preliminary bioassay results showed some of the analogs exhibit excellent antitumor activity against MCF-7 and HepG2, especially four compounds , including I, exhibited higher activity than the pos. control gefitinib. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Application of 70291-62-2).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

General preparation of 3-aryl-3,4-dimethylpentan-4-olides by intramolecular rearrangement was written by Tsatsas, Georges;Cotakis, G.. And the article was included in Bulletin de la Societe Chimique de France in 1970.Related Products of 5351-07-5 This article mentions the following:

Treatment of 3,4-RR1C6H3C(Bu-tert)(OH)CH2CO2R2 (I, R = H, MeO; R1 = H, Cl, MeO, Me, Br; R2 = H, Et) with AcCl and Ac2 3,4-RR1C6H3C(Bu-tert):CH2 and II were also isolated from the above reaction with I (R2 = H). II were also prepared from I by reaction with concentrated H2SO4. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Related Products of 5351-07-5).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Theoretical study of the relative acidities of substituted phenylacetonitrile was written by Julg, Andre;Fournon, Claire. And the article was included in Journal de Chimie Physique et de Physico-Chimie Biologique in 1960.Recommanded Product: 2-(2,6-Dibromophenyl)acetonitrile This article mentions the following:

The L.C.A.O.-M.O. method is used to calculate the energies of PhCH₂CN and (PhCHCN)^– and of derivatives substituted in the nucleus. The difference between the ion and the undissociated mol. is taken as a measure of the acidity. Values for the Coulomb and exchange integrals are chosen from the literature. The following comps. RCH₂CN are arranged according to decreasing acidity (R and relative dissociation energy in terms of β); p-NO₂C₆H₄, 7.41; p-BrC₆H₄, 7.35; Ph, 7.34; 3,5-dimethylphenyl, 7.34; 2,6-dibromophenyl, 7.25; 3,5-dibromophenyl, 7.22; 2,4,6-trimethylphenyl, 7.20; H, 6.56. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9Recommanded Product: 2-(2,6-Dibromophenyl)acetonitrile).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) 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: 2-(2,6-Dibromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of strontium ranelate was written by Sun, Ningning;Wang, Decai;Jiang, Jian. And the article was included in Huagong Shikan in 2007.Application of 58168-20-0 This article mentions the following:

The improved synthetic method for strontium ranclate was realized from citric acid by decarboxylation, esterification, cyclization, alkylation, hydrolyzation and then salt formation. The total yield reached 58.6%. The improved technol. condition is moderate, the operating is simple, and adapts industrialization production In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Application of 58168-20-0).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application of 58168-20-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts