Month: December 2022

Zhang, Kun published the artcileSynthetic Diversity from a Versatile and Radical Nitrating Reagent, Quality Control of 5153-73-1, the publication is Chemistry – A European Journal (2019), 25(56), 12929-12939, database is CAplus and MEDLINE.

A new methodol. was described for the activation of N-nitrosuccimide for the direct synthesis of β-nitroalkenes, β-nitrohydrins, β-nitroethers, isoxazolines I [R = Me, cyclopropyl; R¹ = n-heptyl, Bn, CH₂OPh; R² = H, R¹R² = (CH₂)₄, (CH₂)₉, (CH₂)₁₀C(O)(CH₂)₃; R³ = H, Me] and isoxazoles II [R⁴ = CO₂Et, CH₂CH₂Br, cyclohexyl, etc.]. Detailed mechanistic studies strongly suggested that a mesolytic N-N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, ESR spectroscopy, direct evidence of a nitryl radical in solution by nitrone spin-trapping was observed To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C-H partners to prepare isoxazolines I and isoxazoles II was presented. This approach allowed for the formation of an in situ nitrile oxide from a ketone partner, the presence of which was detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeded in a single-operational step using a mild, regioselective and general protocol with broad chemoselectivity.

Chemistry – A European Journal 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 C12H10N2O5, Quality Control of 5153-73-1.

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

Manna, Srimanta published the artcileSynthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO, SDS of cas: 5153-73-1, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(46), 5286-5288, database is CAplus and MEDLINE.

Nitroolefins are usually synthesized using the Henry reaction. Here, the authors report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from α,β-unsaturated carboxylic acids using tert-butylnitrite (t-BuONO) and TEMPO. α,β-Unsaturated carboxylic acids bearing β-aromatic and β-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.

Chemical Communications (Cambridge, United Kingdom) 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, SDS of cas: 5153-73-1.

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

Natte, Kishore published the artcilePalladium-Catalyzed Trifluoromethylation of (Hetero)Arenes with CF₃Br, Formula: C9H6F3NO, the publication is Angewandte Chemie, International Edition (2016), 55(8), 2782-2786, database is CAplus and MEDLINE.

The CF₃ group is an omnipresent motif found in many pharmaceuticals, agrochems., catalysts, materials, and industrial chems. Despite well-established trifluoromethylation methodologies, the straightforward and selective introduction of such groups into (hetero)arenes using available and less expensive sources is still a major challenge. In this regard, the selective synthesis of various trifluoromethyl-substituted (hetero)arenes by palladium-catalyzed C-H functionalization is herein reported. This novel methodol. proceeds under comparably mild reaction conditions with good regio- and chemoselectivity. As examples, trifluoromethylations of biol. important mols., such as melatonin, theophylline, caffeine, and pentoxifylline, are showcased.

Angewandte Chemie, International Edition published new progress about 261951-87-5. 261951-87-5 belongs to nitriles-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Nitrile,Benzene,Ether, name is 4-Methoxy-3-(trifluoromethyl)benzonitrile, and the molecular formula is C9H6F3NO, Formula: C9H6F3NO.

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

Taylor, Edward C. published the artcilePteridines. XXXVII. A total synthesis of L-erythro-biopterin and some related 6-(polyhydroxyalkyl)pterins, Safety of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of the American Chemical Society (1976), 98(8), 2301-7, database is CAplus and MEDLINE.

6-(1-Erythro-1′,2′-dihydroxypropyl)pterin was prepared by cupric acetate oxidation of 5-deoxy-L-arabinose to its osone, transoximation with acetone oxime to the α-ketoaldoxime, condensation with benzyl α-aminocyanoacetate methanesulfate to give II, cyclization with guanidine to biopterin 8-oxide, and deoxygenation with sodium dithionite. The overall yield was 12%. In analogous fashion, 6-(D-arabino-tetrahydroxybutyl)pterin and 6-D-threo-trihydroxypropyl)pterin were prepared from D-glucose and D-xylose, resp.

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 C28H29NO4, Safety of 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Taylor, Edward C. published the artcilePteridines. XXXIV. Synthesis of 8-hydroxy-7(8H)-pteridinones (pteridine hydroxamic acids), Formula: C10H11N3O3S, the publication is Journal of Organic Chemistry (1975), 40(16), 2332-6, database is CAplus and MEDLINE.

A series of 2,4-diamino-6-alkyl-substituted 8-hydroxy-7(8H)-pteridinones (pteridinehydroxamic acids) (I) was prepared from 2,4-diamino-6-substituted pteridine 8-oxides by chlorination in glacial AcOH, followed by cleavage of the resulting pteridinehydroxamic acid anhydrides II with ethanolic HCl. An alternative but less satisfactory route to 2,4-diamino-6-methyl-8-hydroxy-7(8H)-pteridinone involved condensation of pyruvohydroxamoyl chloride with aminomalononitrile tosylate to give 2-amino-3-cyano-5-methyl-6-chloropyrazine 1-oxide, hydrolysis to the pyrazinehydroxamic acid III, and cyclization with guanidine.

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 C12H15ClO3, Formula: C10H11N3O3S.

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

Rastogi, Roopa R. published the artcileNovel method for the synthesis of substituted and fused 3-cyano-4-(methylmercapto)-2(1H)-pyridones using α-oxoketene S,S-diacetals, Synthetic Route of 57663-05-5, the publication is Journal of the Chemical Society, Chemical Communications (1975), 645, database is CAplus.

RCOCH:C(SMe)2 (R = Me, p-MeC6H4, 3-pyridyl) with cyanoacetamide and Me2CHONa in refluxing Me2CHOH gave 65-85% pyridone I. Similar reaction of the cycloalkanones II (n = 1 and 2) and III gave 77% pyrindinone IV (n = 1), 76% quinolinone IV (n = 2), and 65% benzoquinoline V.

Journal of the Chemical Society, Chemical Communications 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, Synthetic Route of 57663-05-5.

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

Kumar, Arvind published the artcileKetene dithioacetals. Part 11. Reaction of 3-cyano-4-methylthio-2(1H)-pyridones with hydrazine and guanidine: synthesis of novel substituted and fused pyrazolo[4,3-c]pyridone and pyrido[4,3-d]pyrimidine derivatives, HPLC of Formula: 57663-05-5, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1978), 857-62, database is CAplus.

The N-methylpyridones I [R = Me, R¹ = H, R² = 4-R³C₆H₄, R³ = H, Me, MeO, Cl, Br; R = R² = Me, R¹ = H; R = Me, R¹R² = (CH₂)₃, (CH₂)₄] and the benzoquinolone II (R = Me, R¹ = H, n = 1) were prepared by alkylation of I (R = H, R¹, R² as before) and II (R = R¹ = H, n = 1), resp., with Me₂SO₄-NaOMe, followed by heating the mixture of N-Me and O-Me products with MeI. Treatment of I (R = H, Me, R¹ = H, R² = 4-R³C₆H₄, R³ = H, Me, MeO, Cl, Br; R = R² = Me, R¹ = H; R = R¹ = H, R² = 3-, 4-pyridyl; R = H, R¹ = Ph, R² = Me) with NH₂NH₂ in refluxing Me₂CHOH gave 70-90% pyrazolopyridones III. Similar treatment of I [R = H, Me, R¹R² = (CH₂)₃, (CH₂)₄; R = H, R¹R² = (CH₂)₅] and II (R = H, Me, MeO, R¹ = H, n = 1; R = R¹ = H, n = 2) gave 68-80% III (R, R¹, R² as before) and 64-78% pyrazolopyridone IV (R, R¹, n as before), resp. Reaction of I [R = Me, R¹ = H, R² = 4-R³C₆H₄, R³ = H, Me, MeO, Cl, Br; R = Me, R¹R² = (CH₂)₃, (CH₂)₄] and II (R = Me, R¹ = H, n = 1) with guanidine in the presence of 2 mol of NaOEt gave 31-71% pyridopyrimidinone V (R, R¹, R² as before) and 41% pyrimidoquinolinone VI.

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, HPLC of Formula: 57663-05-5.

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

Barnathan, Gilles published the artcileSynthesis of C-nucleosides. XI. 2-D-Arabinofuranosylimidazoles and 8-D-arabinofuranosylpurines, Related Products of nitriles-buliding-blocks, the publication is European Journal of Medicinal Chemistry (1976), 11(1), 67-72, database is CAplus.

The nucleoside analogs I (R = NH2, SH, R1 = H) were prepared by treating II (R1 = R2 = Bz, R3 = Cl, Br) with Hg(CN)2, cleaving benzoyl groups from II (R1 = R2 = Bz, R3 = CN), treating II (R1 = Bz, R2 = H, R3 = CN) with PhCH2SH, cyclizing II (R1 = Bz, R2 = H, R3 = CH(:NH)SCH2Ph) with H2NCH(CN)2, cyclizing II (R1 = Bz, R2 =H, R3 = 4-cyano-5-amino-2-imidazolyl) with HC(:NH)NH2 or HC(OEt)3 and NaSH, and cleaving the benzoyl groups from I (R1 = Bz).

European Journal of 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

Moreland, D. E. published the artcileComparative effects of dichlobenil and its phenolic alteration products on photo- and oxidative phosphorylation, Name: 2,6-Dichloro-3-hydroxybenzonitrile, the publication is Pesticide Biochemistry and Physiology (1974), 4(3), 356-64, database is CAplus.

The effects of dichlobenil (2,6-dichlorobenzonitrile)(I) [1194-65-6] and its phenolic degradation products, 2,6-dichloro-3-hydroxybenzonitrile (II) [3336-34-3] and 2,6-dichloro-4-hydroxybenzonitrile (III) [3336-19-4] on electron transport and phosphorylation were studied in isolated spinach (Spinacia oleracea) chloroplasts and mung bean (Phaseolus aureus) mitochondria. II and III inhibited photoreduction, coupled phosphorylation, and cyclic phosphorylation in chloroplasts and acted as uncouplers of oxidative phosphorylation in mitochondria. II and III also decreased ATP in mung bean hypocotyls. In all assays only limited inhibition was caused by I, even at relatively high concentrations (1.0 mM).

Pesticide Biochemistry and Physiology published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, Name: 2,6-Dichloro-3-hydroxybenzonitrile.

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

Han, Xinya published the artcileBiological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase, Formula: C9H6N2O2, the publication is Bioorganic & Medicinal Chemistry (2020), 28(18), 115624, database is CAplus and MEDLINE.

Herein, a series of nitrostyrene derivatives I (R¹ = H, F, Me, etc.; R² = H, Cl, Me, etc.; R³ = H, Cl, Br, Me) were synthesized, and their inhibitory activities against Fructose-1,6-bisphosphatase (FBPase) were investigated in vitro. Most of the prepared compounds exhibit potent FBPase inhibition (IC₅₀ < 10μM). Specifically, when the substituents of F, Cl, OMe, CF₃, OH, CO₂H, or 2-nitrovinyl were installed at the R² (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5-55 folds compared to those compounds with the same groups at the R¹ (para-) position. In addition, the preferred substituents at the R³ position were Cl or Br, thus compound I (R¹ = NO₂; R² = H; R³ = Cl) exhibited the most potent inhibitory activity (IC₅₀ = 0.15μM). The mol. docking and site-directed mutation suggest that C128 and N125 are essential for the binding of I (R¹ = NO₂; R² = H; R³ = Cl) and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R³ position is Cl > H > CH₃. CoMSIA anal. is consistent with proposed binding mode. The effect of compounds I (R¹ = 1,2,4-triazol-1-yl; R² = H; R³ = H) and I (R¹ = NO₂; R² = H; R³ = Cl) on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100μM, resp.

Bioorganic & Medicinal 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, Formula: C9H6N2O2.

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