Month: December 2022

Li, Gen published the artcileP(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate, Synthetic Route of 214360-44-8, the publication is Journal of the American Chemical Society (2020), 142(38), 16205-16210, database is CAplus and MEDLINE.

The direct reductive N-arylation of nitromethane by organophosphorus-catalyzed reductive C-N coupling with arylboronic acid derivatives is reported. This method operates by the action of a small ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) together with a mild terminal reductant hydrosilane to drive the selective installation of the methylamino group to (hetero)aromatic boronic acids and esters. This method also provides for a unified synthetic approach to isotopically labeled N-methylanilines from various stable isotopologues of nitromethane (i.e., CD₃NO₂, CH₃¹⁵NO₂, and ¹³CH₃NO₂), revealing this easy-to-handle compound as a versatile precursor for the direct installation of the methylamino group.

Journal of the American Chemical Society 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, Synthetic Route of 214360-44-8.

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

Zhu, Yadong published the artcileOrganocatalytic enantioselective Michael addition of cyclic hemiacetals to nitroolefins: a facile access to chiral substituted 5- and 6-membered cyclic ethers, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic & Biomolecular Chemistry (2015), 13(16), 4769-4775, database is CAplus and MEDLINE.

An efficient aminocatalytic enantioselective Michael addition of readily available cyclic hemiacetals to nitroolefins has been developed. The strategy serves as a powerful approach to synthetically valuable chiral 3-substituted tetrahydrofurans (THFs) I [R = Et, Ph, 3-NO₂-C₆H₄, etc.] and tetrahydropyrans (THPs) II. The synthetic utilities of the versatile Michael adducts also have been demonstrated in the synthesis of 2,3-disubstituted cyclic ethers, α-substituted lactones and venlafaxine analogs.

Organic & Biomolecular Chemistry 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 C11H15NO2, Application of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Mehta, K. J. published the artcilePreparation and antimicrobial activity of p-chloro-p’-(α-carbamoylbenzylamino)diphenyl sulfones and 3-amino-2-aryl-5-p-chlorophenylsulfonylindoles, Quality Control of 13312-84-0, the publication is Acta Ciencia Indica, Chemistry (1985), 11(3), 187-90, database is CAplus.

4-ClC₆H₄SO₂C₆H₄NHCHRR¹ (I, R = Ph, 2-HOC₆H₄, 3-HOC₆H₄, 4-HOC₆H₄, MeOC₆H₄, 2-ClC₆H₄, 4-ClC₆H₄, 3,4-MeO(HO)C₆H₃, PhCH:CH, 4-O₂NC₆H₄, 2-furyl; R¹ = cyano) were prepared by treating RCH(OH)CN with 4-ClC₆H₄SO₂C₆H₄NH₂-4. Treatment of I (R¹ = cyano) with H₂SO₄ for 2 days gave I (R¹ = CONH₂) whereas after 7 days the indoles II were obtained. I (R¹ = CONH₂) have bactericidal activity against Staphylococcus aureus and Escherichia coli (no data).

Acta Ciencia Indica, 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, Quality Control of 13312-84-0.

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

Rokade, Balaji V. published the artcileSynthesis of substituted nitroolefins: a copper catalyzed nitrodecarboxylation of unsaturated carboxylic acids, COA of Formula: C9H6N2O2, the publication is Organic & Biomolecular Chemistry (2013), 11(39), 6713-6716, database is CAplus and MEDLINE.

A novel, mild and convenient method for the nitrodecarboxylation of substituted cinnamic acid derivatives to their nitroolefins is achieved using a catalytic amount of CuCl (10 mol%) and tert-Bu nitrite (2 equivalent) as a nitrating agent in the presence of air. This reaction provides a useful method for the synthesis of β,β-disubstituted nitroolefin derivatives, which are generally difficult to access from other conventional methods. Addnl., this reaction is selective as the E-isomer of the acid derivatives furnishes the corresponding E-nitroolefins. One more salient feature of the method is, unlike other methods, no metal nitrates or HNO₃ are employed for the transformation.

Organic & Biomolecular Chemistry 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, COA of Formula: C9H6N2O2.

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

Kovtunenko, V. A. published the artcileCondensed isoquinolines. 38*. azolo[b]isoquinolines from 2-(halomethyl)benzoic acid derivatives, COA of Formula: C8H6ClN, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2011), 47(8), 996-1005, database is CAplus.

On interacting 2-(chloromethyl)-, 2-(bromomethyl)benzonitrile or Me 2-(bromomethyl)benzoate with 1-R-1H-imidazoles and 1-R-1H-benzimidazoles quaternary diazolium salts are formed, the heating of which with bases (K₂CO₃, Et₃N) led to the intramol. acylation products, 1-alkyl-10-amino-1H-imidazo[1,2-b]isoquinolin-4-ium halides, 5-alkyl-6-amino-5H-benzimidazo[1,2-b]isoquinolin-12-ium halides, or 1-alkyl-1H-imidazo[1,2-b]isoquinolin-4-ium-10-olate halides.

Chemistry of Heterocyclic Compounds (New York, NY, United States) 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, COA of Formula: C8H6ClN.

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

Taylor, Edward C. published the artcilePteridines. XXXVIII. Synthesis of some 2,4-diamino-6-substituted methylpteridines. New route to pteroic acid, Safety of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of Organic Chemistry (1975), 40(16), 2347-51, database is CAplus.

6-Substituted 2,4-diaminopteridines I and 6-substituted pterins II (R = Cl, OH, H, p-ClC6H4, p-EtO2CC6H4NH, PhCH2, etc.) were prepared by reaction of 2-amino-3-cyano-5-chloromethylpyrazine with nucleophiles, followed by ring closure with guanidine to give I, and final acid hydrolysis to II. The pyrazine oxides III (R = PhCH2S, p-O2NC6H4NMe, p-O2NC6H4NH) were prepared by treating XCH2COCH:NOH (X = Cl, Br) with H2NCH(CN)2.p-MeC6H4SO3H and nucleophiles.

Journal of Organic Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C5H6N2O2, Safety of 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Li, Kelin published the artcileEnantioselective addition of amines to alkenoyl-N-oxazolidinones, Category: nitriles-buliding-blocks, the publication is Tetrahedron (2005), 61(26), 6237-6242, database is CAplus.

Investigations of cationic Pd(II) complex I as hydroamination catalyst led to the development of highly enantioselective addition of aromatic amines 4-R²C₆H₄NH₂ (R² = H, Cl, Me, MeO) to alkenoyl-N-oxazolidinones II (R¹ = Me, Et, n-Pr), giving aminated products III (configuration unassigned) with ee values up to 93%. Factors affecting the yield and selectivity of the reaction were described. Addition of substituted benzylamines IV (R¹ = H, R² = H, MeO, Me; R¹ = R² = MeO; R¹ = Br, R² = H) to these Michael acceptors was also attempted, and was found to be reversible under catalytic conditions.

Tetrahedron published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Category: nitriles-buliding-blocks.

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

Juhl, Martin published the artcileCO₂-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions, Category: nitriles-buliding-blocks, the publication is Chemistry – A European Journal (2021), 27(1), 228-232, database is CAplus and MEDLINE.

Use of carbon dioxide/carbon disulfide to accelerate cyanohydrin RR¹COHCN [R = cyclohexyl, Ph, 2-furyl, etc.; R¹ = H, CO₂H] and R²CHOC(S)SMeCN [R² = 4-FC₆H₄, (CH₂)₂Ph] syntheses starting from alkyl- and aryl aldehydes under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN were reported. Under inert atm., the reaction was essentially not operative due to the unfavored equilibrium The utility of CO₂-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani-Fischer synthesis under neutral conditions. This protocol offered an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atm. pressure of CO².

Chemistry – A European Journal 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, Category: nitriles-buliding-blocks.

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

Taylor, Edward C. published the artcilePteridines. XXIX. Unequivocal route to 2,4-diamino-6-substituted pteridines, Application In Synthesis of 5098-14-6, the publication is Journal of the American Chemical Society (1973), 95(19), 6413-18, database is CAplus.

2,4-Diamino-6-substituted pteridines (I) are prepared Reaction of an α-keto-aldoxime with aminomalononitrile gives 2-amino-3-cyano-5-substituted pyrazine 1-oxides which yield 2,4-diamino-6-substituted pteridine 8-oxides upon cyclization with guanidine. 2,4-Diaminopteridines are then obtained by deoxygenation of the corresponding 8-oxides, or alternately by prior deoxygenation of these pyrazine 1-oxides, followed by cyclization with guanidine. The conversion of 2-amino-3-cyano-5-methylpyrazine 1-oxide to the corresponding 1,4-dioxide, and a number of chem. transformations of this latter intermediate, are also described.

Journal of the American Chemical Society published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C3H8N2S, Application In Synthesis of 5098-14-6.

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

Baraldi, Pier Giovanni published the artcileAntimicrobial and antitumor activity of N-heteroimmine-1,2,3-dithiazoles and their transformation in triazolo-, imidazo-, and pyrazolopyrimidines, Related Products of nitriles-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry (2001), 10(2), 449-456, database is CAplus and MEDLINE.

The reaction of Appel’s salt with o-aminonitrile heterocyclics gave the corresponding 4-chloro-5-heteroimmine-1,2,3-dithiazoles which were evaluated for their antibacterial, antifungal and antitumor activity. Although all these N-heteroimines were devoid of significant antibacterial activity, they showed significant antifungal activity. Moreover, the same derivatives represent highly versatile intermediates in heterocyclic synthesis, in fact the pyrazoleiminodithiazoles can be converted in one step into 2-cyano derivatives of the corresponding 4-methoxy-pyrazolo[3,4-d]pyrimidines by sodium methoxide in refluxing methanol. This provides a general and attractive route to 4-methoxy-6-cyanopyrazolo[3,4-d]pyrimidines from 1-substituted 5-amino pyrazoles in two simple steps. Finally, the isosteric replacement of the pyrazole ring atoms to give the imidazole[3,4-d]pyrimidine and triazole [4,5-d]pyrimidine ring systems was examined

Bioorganic & Medicinal Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Related Products of nitriles-buliding-blocks.

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