Category: nitriles-buliding-blocks

Kang, Taeho published the artcileAlkene Difunctionalization Directed by Free Amines: Diamine Synthesis via Nickel-Catalyzed 1,2-Carboamination, SDS of cas: 214360-44-8, the publication is ACS Catalysis (2022), 12(7), 3890-3896, database is CAplus.

A versatile method to access differentially substituted 1,3- and 1,4-diamines RNH(CH₂)₂CH(R¹)CH₂R² (R = H, Me, Bn, pyrimidin-2-yl, etc.; R¹ = piperidin-1-yl, 1,4-dioxa-8-azaspiro[4.5]decan-8-yl, diethylaminyl; R² = Ph, naphthalen-1-yl, 1-benzofuran-5-yl, etc.) via a nickel-catalyzed three-component 1,2-carboamination of alkenyl amines RNH(CH₂)₂CH=CH₂ with aryl/alkenylboronic ester nucleophiles R³COOR¹ (R³ = t-Bu, Ph, morpholin-4-yl, etc.) and N-O electrophiles R²B(nep) was reported. The reaction proceeds efficiently with free primary and secondary amines without needing a directing auxiliary or protecting group, and is enabled by fine-tuning the leaving group on the N-O reagent. The transformation is highly regioselective and compatible with a wide range of coupling partners and alkenyl amine substrates, all performed at room temperature A series of kinetic studies support a mechanism in which alkene coordination to the nickel catalyst is turnover-limiting.

ACS Catalysis published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, SDS of cas: 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Fairley, Gary published the artcileOne-pot synthesis of novel 1,2,6,7-tetrahydro-3H-pyrazolo[4,3-c]pyridine-3,4(5H)-diones, SDS of cas: 49540-34-3, the publication is Tetrahedron Letters (2018), 59(39), 3574-3578, database is CAplus.

A facile synthesis of novel 1,2,6,7-tetrahydro-3H-pyrazolo[4,3-c]pyridine-3,4(5H)-diones was achieved. The operationally simple procedure, using readily available intermediates, allows for rapid derivatization of the pharmacophore with alkyl, aryl and heteroaryl substituents.

Tetrahedron Letters published new progress about 49540-34-3. 49540-34-3 belongs to nitriles-buliding-blocks, auxiliary class Aliphatic Chain, name is Ethylhydrazine dihydrochloride, and the molecular formula is C2H10Cl2N2, SDS of cas: 49540-34-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

McEwen, William E. published the artcileSynthetic uses of open-chain analogs of Reissert compounds, Related Products of nitriles-buliding-blocks, the publication is Journal of Organic Chemistry (1980), 45(7), 1301-8, database is CAplus.

Open-chain analogs, RN(COR²)CHR¹CN (I, R = Ph, PhCH₂, p-ClC₆H₄, p-MeOC₆H₄, Me(CH₂)₅, cyclohexyl; R¹ = Ph, H, o-, m-, p-ClC₆H₄, 3,4-(MeO)₂C₆H₃, o-, m-MeOC₆H₄, Bu; R² = Ph, Me), of Reissert compounds are obtained by reaction of R¹CH(OH)CN with RNH₂, the resulting aminonitriles, RNHCHR¹CN, then being acylated. Hydrofluoroborate salts, II, of I, are prepared by reaction with fluoroboric acid in HOAc. The salts, II, undergo 1,3-dipolar addition reactions with reactive alkynes to give substituted pyrroles and with Et acrylate to give a different type of substituted pyrrole, the initial step in this instance being a Diels-Alder reaction. Thus, addition of MeO₂CCCCO₂Me to II (R¹ = R² = Ph) gave III (R = Ph, m-ClC₆H₄, p-MeOC₆H₄, PhCH₂); and addition of H₂C:CHCO₂Et to II (R = R¹ = R² = Ph) gave IV. I also undergo base-catalyzed reactions, such as alkylation with R⁵Br to provide R²CONRCR¹R⁵CN (R⁵ = PhCH₂, Bu, α-naphthylmethyl, R-R² = as above), which, in turn, undergo cleavage reactions in ethanolic alkali to give ketones R¹R⁵CO. A conjugate addition reaction of the anion BzNPhC^–PhCN (V) to Me acrylate to give, after subsequent steps, VI was demonstrated. α-Anilino ketones, PhNHCHRCOR¹, result when the anion V is treated with aldehydes, the initial reaction mixtures being subjected to subsequent alk. hydrolysis. Finally, N-benzyl Reissert analogs give desoxybenzoins plus benzonitriles on treatment with NaH in THF.

Journal of Organic Chemistry published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Li, Si-Yuan published the artcilePractical copper-catalyzed chloronitration of alkenes with TMSCl and guanidine nitrate, Quality Control of 5153-73-1, the publication is Organic Chemistry Frontiers (2020), 7(17), 2449-2455, database is CAplus.

A novel and practical chloronitration of alkenes in the presence of easily available TMSCl and guanidine nitrate was developed by using cheap copper sulfate pentahydrate as the catalyst. A variety of vic-chloronitro compounds were directly synthesized in good to excellent yields on up to 100 mmol scale under mild reaction conditions, and the resulting products could be smoothly transformed into the corresponding nitroalkenes and diverse nitro compounds bearing a vicinal nucleophilic “C”, “N” or “S” unit.

Organic Chemistry Frontiers published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Quality Control of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Chen, Yi-Hung published the artcilePreparation and Application of Solid, Salt-Stabilized Zinc Amide Enolates with Enhanced Air and Moisture Stability, Recommanded Product: 2-(Chloromethyl)benzonitrile, the publication is Angewandte Chemie, International Edition (2017), 56(16), 4612-4616, database is CAplus and MEDLINE.

The treatment of various N-morpholino amides with TMPZnCl·LiCl (TMP=2,2,6,6-tetramethylpiperidyl) and Mg(OPiv)₂ in THF at 25 °C provides solid zinc enolates with enhanced air and moisture stability (t_1/2 in air: 1-3 h) after solvent evaporation These enolates undergo Pd- and Cu-catalyzed cross-couplings with (hetero)aryl bromides as well as allylic and benzylic halides. The arylated N-morpholino amides were converted into various ketones by LaCl₃·2 LiCl mediated acylation with Grignard reagents. The new, solid enolates were used to prepare a potent anti-breast-cancer drug candidate in six steps and 23 % overall yield.

Angewandte Chemie, International Edition published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Recommanded Product: 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Yosef, Hisham Abdallah A. published the artcileSynthesis and biological evaluation of some novel chiral carbamates and 4-imino-2- oxazolidinones derived from selected optically active cyanohydrins, Application of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Pharma Chemica (2017), 9(16), 6-21, database is CAplus.

The reaction of tert-Bu isocyanate with the optically active cyanohydrins was accompanied with inversion of configuration giving the chiral (S)-enantiomers of the resp. carbamate derivatives On the other hand, reactions of aryl isocyanate reagents Ar-N=C=O with cyanohydrins gave the corresponding optically active 4-imino-2-oxazolidinone derivatives in the form of their S-configuration. Moreover, the same reactions were also applied for the racemic cyanohydrins to afford the corresponding carbamates and/or 4-imino-2-oxazolidinones as racemic mixtures Structures of the new products were elucidated with compatible micro anal. and spectroscopic (IR, ¹H-NMR, ¹³C-NMR and MS) measurements. The X-ray crystallog. anal. provided an efficient tool in confirming the structure and configuration of the new chiral compounds The antimicrobial activity of selected new derivatives against four bacterial species (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa) and two fungi (Aspergillus flavus and Candida albicans) were evaluated. Moreover, some of the new products were screened for their in-vitro antitumor activity against the human solid cancer cell lines, human carcinoma (HCT116), human hepatocellular liver carcinoma (HepG2) and human breast adenocarcinoma (MCF-7) cell lines. Generally, most of the investigated compounds were showed moderate to high activities in comparison with the standard drugs. The structure-activity relationship (SAR) was also discussed.

Pharma Chemica published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C2H5BF3K, Application of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Abu-Shanab, Fathi A. published the artcileα,α-Dioxoketene dithioacetals as starting materials for the synthesis of polysubstituted pyridines, Category: nitriles-buliding-blocks, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1994), 1449-52, database is CAplus.

Reactions of 3-acetyl-4,4-bis(methylthio)but-3-en-2-one and Me 2-acetyl-3,3-bis(methylthio)-prop-2-enoate with cyanothioacetamide, cyanoacetamide, or 2-amino-1,3,3-tricyanoprop-1-ene and base, followed by treatment with acid, give polysubstituted pyridines. Further elaboration of these products leads to bicyclic systems such as thieno[2,3-b]pyridines and pyrazolo[3,4-c]pyridine and then to tricyclic systems including pyrazolo[3,4-d]thieno[2,3-b]pyridine and dipyrazolo[3,4-b:3′,4′-d]pyridine.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 57663-05-5. 57663-05-5 belongs to nitriles-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Tetrahydropyrimidins, name is 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile, and the molecular formula is C8H8N2OS, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Eskandariyan, Zahra published the artcileSynthesis of thioether derivatives of quinazoline-4-one-2-thione and evaluation of their antiplatelet aggregation activity, Category: nitriles-buliding-blocks, the publication is Archives of Pharmacal Research (2014), 37(3), 332-339, database is CAplus and MEDLINE.

A series of 2-(arylmethylthio)-3-phenylquinazolin-4-one derivatives have been synthesized and their antiplatelet aggregation activities were assessed against ADP and arachidonic acid-induced platelet aggregation in human plasma. Among the tested thioethers, derivative 2, 3, 5 and 16 were the most potent compounds with satisfactory IC₅₀ for inhibition of platelet aggregation induced by ADP. Anal. of global physicochem. parameters shows some correlations between activities and mol. volume and also surface area of the studied derivatives

Archives of Pharmacal Research published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Guerrero-Corella, Andrea published the artcile2-Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Angewandte Chemie, International Edition (2018), 57(19), 5350-5354, database is CAplus and MEDLINE.

An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a large variety of α,γ-diamino acid derivatives with excellent stereoselectivity.

Angewandte Chemie, International Edition published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Diosdado, Saioa published the artcileCatalytic Enantioselective Synthesis of Tertiary Thiols From 5H-Thiazol-4-ones and Nitroolefins: Bifunctional Ureidopeptide-Based Bronsted Base Catalysis, Computed Properties of 5153-73-1, the publication is Angewandte Chemie, International Edition (2013), 52(45), 11846-11851, database is CAplus and MEDLINE.

The synthesis of the target compounds was achieved using urea-peptide analogs as catalysts (Bronsted acids). A reaction of amino acids (L-valine, 3-methyl-L-valine) with (8α,9S)-6′-methoxycinchonan-9-amine (epiquinine, cinchona alkaloid derivative) provided the above-mentioned urea-peptide analogs. These catalysts were applied in a Michael reaction of thiazolone derivatives with (nitro)alkenes. A reaction of 2-mercaptobutanoic acid, 2-(mercapto)octanoic acid, α-(mercapto)benzenepropanoic acid with nitriles provided 4-thiazolol derivatives (4-thiazolone derivatives). The title compounds thus formed included a thiazolone nitroalkane derivative (I) and related substances, quinoline derivatives, naphthalene derivatives, etc.

Angewandte Chemie, International Edition published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Computed Properties of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts