Month: December 2022

Malapit, Christian A. published the artcileMechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides, Application of 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Journal of the American Chemical Society (2019), 141(43), 17322-17330, database is CAplus and MEDLINE.

This Article describes the development of a base-free, Ni-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate ester products. Detailed studies were conducted to assess the relative rates of direct transmetalation between aryl boronate esters and diboron reagents and a bisphosphine Ni(aryl)(fluoride) intermediate. These studies revealed that diboron reagents undergo transmetalation with this Ni(aryl)(fluoride) intermediate at rates significantly faster than their aryl boronate ester congeners. Also, the reactivity of both B reagents toward transmetalation is enhanced with increasing electrophilicity of the B center. These mechanistic insights were leveraged to develop a catalytic decarbonylative borylation of acid fluorides that proved applicable to a variety of (hetero)aryl carboxylic acid fluorides as well as diverse diboron reagents. The acid fluorides can be generated in situ directly from carboxylic acids. Also, the mechanistic studies directed the identification of various air-stable Ni pre-catalysts for this transformation.

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, Application of 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

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

Tuo, Wei published the artcileDevelopment of novel oxazolo[5,4-d]pyrimidines as competitive CB₂ neutral antagonists based on scaffold hopping, Application In Synthesis of 5098-14-6, the publication is European Journal of Medicinal Chemistry (2018), 68-78, database is CAplus and MEDLINE.

A series of novel oxazolo[5,4-d]pyrimidines I [R¹ = H, Cl, F, CF₃; R² = H, Me; R³ = n-Bu, cyclohexylmethyl, 1-methylpiperazinyl, etc.] was designed via a scaffold hopping strategy and synthesized through a newly developed approach. All these compounds I were evaluated for their biol. activity toward CB₁/CB₂ cannabinoid receptors, their metabolic stability in mice liver microsomes and their cytotoxicity against several cell lines. Eight compounds I [R¹ = Cl, CF₃; R² = H, Me; R³ = 1-methylpiperazinyl, 1-ethylpiperazinyl, 1-acetylpiperazinyl] were identified as CB₂ ligands with K_i values less than 1 ΜM. It was noteworthy that compounds I [R¹ = Cl; R² = Me; R³ = 1-methylpiperazinyl, 1-ethylpiperazinyl] showed CB₂ binding affinity in the nanomolar range and significant selectivity over CB₁ receptors. Interestingly, functionality studies imply that they behaved as competitive neutral antagonists. Moreover, all tested compounds I were devoid of cytotoxicity toward several cell lines, including Chinese hamster ovary cells (CHO) and human colorectal adenocarcinoma cells HT29.

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 C12H16O3, Application In Synthesis of 5098-14-6.

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

Walker, Sarah E. published the artcileLigand- and Base-Free Pd(II)-Catalyzed Controlled Switching between Oxidative Heck and Conjugate Addition Reactions, COA of Formula: C10H12F6N4O6PdS2, the publication is Organic Letters (2013), 15(8), 1886-1889, database is CAplus and MEDLINE.

A simple change of solvent allows controlled and efficient switching between oxidative Heck and conjugate addition reactions on cyclic Michael acceptor substrates, catalyzed by a cationic Pd(II) catalyst system. E.g., in presence of Pd(OAc)₂ and TfOH in ClCH₂CH₂Cl, reaction of 2-cyclohexenone and tris(4-methoxyphenyl)boroxin gave 94% conjugate addition product I. On the other hand, the same reaction conducted in DMSO gave 84% oxidative Heck reaction product II. Both reactions are ligand- and base-free and tolerant of air and moisture, and the controlled switching sheds light on some of the factors which favor one reaction over the other.

Organic Letters 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 C9H21NO3, COA of Formula: C10H12F6N4O6PdS2.

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

Jaiswal, Pradeep Kumar published the artcileAn organocatalytic highly efficient approach to the direct synthesis of substituted carbazoles in water, Formula: C9H6N2O2, the publication is Organic & Biomolecular Chemistry (2013), 11(48), 8410-8418, database is CAplus and MEDLINE.

A simple, mild, green, catalytic and general procedure for the direct synthesis of highly functionalized 1-methoxycarbonyl-2-aryl/alkyl-3-nitro-9H-carbazoles was achieved in water medium via a one-pot domino Michael-Henry/aromatization reaction of Me 2-(3-formyl-1H-indol-2-yl)acetates with aryl/alky-substituted β-nitroolefins under air using DABCO (30 mol%) as an organocatalyst. In addition, the bench scale synthesis can be performed without using toxic organic solvents and a biol. important new fused carbazole was prepared

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, Formula: C9H6N2O2.

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

Jaiswal, Pradeep Kumar published the artcileStereoselective synthesis of highly functionalized tetrahydrocarbazoles through a domino Michael-Henry reaction: an easy access to four contiguous chiral centers, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is RSC Advances (2013), 3(27), 10644-10649, database is CAplus.

For the first time, a very simple, efficient, mild, catalytic and one-step procedure for the synthesis of a series of densely functionalized 1-methoxycarbonyl-2-aryl-3-nitro-4-hydroxy-1,2,3,4-tetrahydro-9H-carbazole derivatives was achieved by a domino Michael reaction-Henry reaction (tandem reaction) of Me 3-formyl-1H-indole-2-acetic acid esters and β-nitrostyrene derivatives using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst. Furthermore, high enantioselectivity (92% enantiomeric excess) and diastereoselectivity (≤12:1 dr) were observed with a chiral organocatalyst and thus, the synthesis of the target compounds was achieved in excellent yield using 9-(benzyl)cupreidine (10 mol%) as catalyst. The title compounds thus formed included a tetrahydro(hydroxy)(nitro)(phenyl)carbazolecarboxylic acid ester derivative (I) and related substances.

RSC Advances 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, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Leal, Raul A. published the artcileApplication of a Palladium-Catalyzed C-H Functionalization/Indolization Method to Syntheses of cis-Trikentrin A and Herbindole B, Application In Synthesis of 68569-14-2, the publication is Angewandte Chemie, International Edition (2016), 55(39), 11824-11828, database is CAplus and MEDLINE.

We describe herein formal syntheses of the indole alkaloids cis-trikentrin A, I, and herbindole B, II, from a common meso-hydroquinone intermediate prepared by a ruthenium-catalyzed [2+2+1+1]-cycloaddition that has not been used previously in natural product synthesis. Key steps include a sterically demanding Buchwald-Hartwig amination as well as a unique C(sp³)-H amination/indole formation. Studies toward a selective desymmetrization of the meso-hydroquinone are also reported.

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, Application In Synthesis of 68569-14-2.

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

Tang, Jie published the artcileCatalytic Decarboxylative Cross-Coupling of Aryl Chlorides and Benzoates without Activating ortho Substituents, Category: nitriles-buliding-blocks, the publication is Angewandte Chemie, International Edition (2015), 54(44), 13130-13133, database is CAplus and MEDLINE.

The restriction of decarboxylative cross-coupling reactions to ortho-substituted or heterocyclic carboxylate substrates was overcome by holistic optimization of a bimetallic Cu/Pd catalyst system. The combination of a CuI/Me₄phen decarboxylation catalyst and a [(MeCN)₄Pd](OTf)₂/XPhos cross-coupling catalyst enables the synthesis of biaryls from inexpensive aryl chlorides and potassium benzoates regardless of their substitution pattern.

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 C4H6N2, Category: nitriles-buliding-blocks.

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

Rani, Dixita published the artcileAsymmetric Michael Addition of Unactivated Ketones with β-Nitrostyrenes Mediated by Bifunctional L-Prolinamide Organocatalysts, Formula: C9H6N2O2, the publication is ChemistrySelect (2020), 5(8), 2435-2440, database is CAplus.

The catalytic activity of two types of L-prolinamide organocatalysts was investigated for asym. Michael addition reaction of cyclic/acyclic ketones with β-nitrostyrens. L-Prolinamides bearing amino groups as efficient catalyst as well as selectivity was found to be dependent upon the position of amine group to the amide bond. Organocatalyst having -NH₂ group ortho to amide bond provided the best results. Substrate scope was also studied by performing the reaction of various β-nitrostyrenes with ketones to afforded the corresponding Michael adducts in excellent yields with very high diastereoselectivities and enantioselectivities in almost all cases.

ChemistrySelect 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

Morwick, Tina published the artcileEvolution of the Thienopyridine Class of Inhibitors of IκB Kinase-β: Part I: Hit-to-Lead Strategies, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of Medicinal Chemistry (2006), 49(10), 2898-2908, database is CAplus and MEDLINE.

High-throughput screening is routinely employed as a method for the identification of novel hit structures. Large numbers of active compounds are typically procured in this way and must undergo a rigorous validation process. This process is described in detail for a collection of screening hits identified as inhibitors of IκB kinase-β (IKKβ), a key regulatory enzyme in the nuclear factor-κB (NF-κB) pathway. From these studies, a promising hit series was selected. Subsequent lead generation activities included the development of a pharmacophore hypothesis and structure-activity relationship (SAR) for the hit series. This led to the exploration of related scaffolds offering addnl. opportunities, and the various structural classes were comparatively evaluated for enzyme inhibition, selectivity, and drug-like properties. A novel lead series of thienopyridines was thereby established, and this series advanced into lead optimization for further development.

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, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Taylor, Edward C. published the artcilePteridines. Part XLII. Synthesis of some benzo[g]pteridines. A novel aromatization reaction, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Heterocycles (1977), 6(4), 449-57, database is CAplus.

The benzopteridine I (R = NH2, R1 = R2 = H) was prepared by condensing 6-chloro-2-oximinocyclohexanone-HCl with H2NCH(CN)2.4-MeC6H4SO3H, aromatizing the quinoxaline oxide II by heating with HOAc, and condensing 2-amino-3-cyanoquinoxaline (III) with guanidine-HCl. Condensation of III with HC(OEt)3 gave I (R-R2 = H). I (R = NH2, R1 = R2 = H) was treated with HCl to give benzo[g]pterin. I [R = NH2, R1R2 = (CH)4] was obtained from 2-oximino-1-tetralone.

Heterocycles 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, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate.

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