Category: nitriles-buliding-blocks

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

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

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

Dianati, Vahid published the artcileImproving the Selectivity of PACE4 Inhibitors through Modifications of the P1 Residue, Application In Synthesis of 5153-73-1, the publication is Journal of Medicinal Chemistry (2018), 61(24), 11250-11260, database is CAplus and MEDLINE.

Paired basic amino acid cleaving enzyme 4 (PACE4), a serine endoprotease of the proprotein convertases family, has been recognized as a promising target for prostate cancer. We previously reported a selective and potent peptide-based inhibitor for PACE4, named the multi-Leu peptide (Ac-LLLLRVKR-NH₂ sequence), which was then modified into a more potent and stable compound named C23 with the following structure: Ac-DLeu-LLLRVK-Amba (Amba: 4-amidinobenzylamide). Despite improvements in both in vitro and in vivo profiles of C23, its selectivity for PACE4 over furin was significantly reduced. We examined other Arg-mimetics instead of Amba to regain the lost selectivity. Our results indicated that the replacement of Amba with 5-(aminomethyl)picolinimidamide increased affinity for PACE4 and restored selectivity. Our results also provide a better insight on how structural differences between S1 pockets of PACE4 and furin could be employed in the rational design of selective inhibitors.

Journal of 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, Application In Synthesis of 5153-73-1.

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

Maity, Soham published the artcileStereoselective Nitration of Olefins with ^tBuONO and TEMPO: Direct Access to Nitroolefins under Metal-free Conditions, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2013), 15(13), 3384-3387, database is CAplus and MEDLINE.

Nitroolefins are essential elements for both synthetic chem. and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-free conditions. A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.

Organic Letters 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, Application of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Pastor, Stephen D. published the artcileSubstituted 5-(D,L-erythro-1′,2′-dihydroxypropyl)pyrazines. Potential precursors for the synthesis of biopterin derivatives, Application In Synthesis of 5098-14-6, the publication is Journal of Heterocyclic Chemistry (1984), 21(3), 657-60, database is CAplus.

Substituted 5-(D,L–erythro-1′,2′-dihydroxypropyl)pyrazines I (R = cyano, CO₂CH₂Ph) were prepared from crotonic acid. Functionalized 2-oximino-3-oxoesters II (R¹ = Me, CMe₃) showed anomalous behavior during decarboxylation. The structures of prepared compounds were determined by spectroscopic methods.

Journal of Heterocyclic 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, Application In Synthesis of 5098-14-6.

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

Boursalian, Gregory B. published the artcilePd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent, Application In Synthesis of 68569-14-2, the publication is Journal of the American Chemical Society (2013), 135(36), 13278-13281, database is CAplus and MEDLINE.

An amine-N-oxide-ligated palladium complex, in conjunction with a silver cocatalyst, catalyzes imidation of arenes by the reagent N-fluorobenzenesulfonimide. The reaction enables imidation of a variety of arenes at or below room temperature, requires no coordinating directing group on the substrate, and gives synthetically useful yields with only 1 equiv of arene. Mechanistic data implicate an unusual mechanism devoid of commonly invoked organometallic intermediates: oxidation of the Pd catalyst occurs as the turnover-limiting step, while C-H bond functionalization occurs subsequently at a high oxidation state of the catalyst.

Journal of the American Chemical Society 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, Application In Synthesis of 68569-14-2.

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

Wentrup, Curt published the artcile3-pyridylnitrene, 2- and 4-pyrimidinylcarbenes, 3-quinolylnitrenes and 4-quinazolinylcarbenes. Interconversion, ring expansion to diazacycloheptatetraenes, ring opening to nitrile ylides and ring contraction to cyanopyrroles and cyanoindoles, Synthetic Route of 26187-28-0, the publication is Beilstein Journal of Organic Chemistry (2013), 743-753, database is CAplus and MEDLINE.

Precursors of 3-pyridylnitrene and 2- and 4-pyrimidinylcarbenes all afford mixtures of 2- and 3-cyanopyrroles on flash vacuum thermolysis, but 3-cyanopyrroles are the first-formed products. 3-Quinolylnitrenes and 4-quinazolinylcarbenes similarly afford 3-cyanoindoles. 2-Pyrimidinylcarbenes rearrange to 3-pyridylnitrenes, but 4-pyrimidinylcarbenes and 4-quinazolinylcarbenes do not necessarily rearrange to the corresponding 3-pyridylnitrenes or 3-quinolylnitrenes. The ring contraction reactions are interpreted in terms of ring opening of either the nitrenes or the diazacycloheptatetraenes to nitrile ylides.

Beilstein Journal of Organic Chemistry published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C2H2N4O2, Synthetic Route of 26187-28-0.

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

August, David P. published the artcileMaximizing Coordination Capsule-Guest Polar Interactions in Apolar Solvents Reveals Significant Binding, Formula: C10H12F6N4O6PdS2, the publication is Angewandte Chemie, International Edition (2016), 55(48), 15022-15026, database is CAplus and MEDLINE.

Guest encapsulation underpins the functional properties of self-assembled capsules yet identifying systems capable of strongly binding small organic mols. in solution remains a challenge. Most coordination capsules rely on the hydrophobic effect to ensure effective solution-phase association In contrast, we show that using non-interacting anions in apolar solvents can maximize favorable interactions between a cationic Pd₂L₄ host and charge-neutral guests resulting in a dramatic increase in binding strength. With quinone-type guests, association constants in excess of 10⁸ M^-1 were observed, comparable to the highest previously recorded constant for a metallosupramol. capsule. Modulation of optoelectronic properties of the guests was also observed, with encapsulation either changing or switching-on luminescence not present in the bulk phase.

Angewandte Chemie, International Edition 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, Formula: C10H12F6N4O6PdS2.

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

Stairs, Shaun published the artcileDivergent prebiotic synthesis of pyrimidine and 8-oxo-purine ribonucleotides, Name: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Nature Communications (2017), 15270, database is CAplus and MEDLINE.

Understanding prebiotic nucleotide synthesis is a long standing challenge thought to be essential to elucidating the origins of life on Earth. Recently, remarkable progress has been made, but to date all proposed syntheses account sep. for the pyrimidine and purine ribonucleotides; no divergent synthesis from common precursors has been proposed. Moreover, the prebiotic syntheses of pyrimidine and purine nucleotides that have been demonstrated operate under mutually incompatible conditions. Here, we tackle this mutual incompatibility by recognizing that the 8-oxo-purines share an underlying generational parity with the pyrimidine nucleotides. We present a divergent synthesis of pyrimidine and 8-oxo-purine nucleotides starting from a common prebiotic precursor that yields the β-ribo-stereochem. found in the sugar phosphate backbone of biol. nucleic acids. The generational relationship between pyrimidine and 8-oxo-purine nucleotides suggests that 8-oxo-purine ribonucleotides may have played a key role in primordial nucleic acids prior to the emergence of the canonical nucleotides of biol.

Nature Communications 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 C8H6ClF3, Name: 2-Aminomalononitrile 4-methylbenzenesulfonate.

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