Category: pyridine-derivatives

Wang, Amu; Liu, Ya-Zhou; Shen, Zhongke; Qiao, Zeen; Ma, Xiaofeng published the artcile< Regioselective Synthesis of Pyrazolo[1,5-a]pyridine via TEMPO-Mediated [3 + 2] Annulation-Aromatization of N-Aminopyridines and α,β-Unsaturated Compounds>, Safety of 3-(Trifluoromethyl)pyridine, the main research area is pyridiniumamine trimethylbenzenesulfonate alkene TEMPO catalyst regioselective annulation aromatization; pyrazolopyridine preparation.

A TEMPO-mediated [3 + 2] annulation-aromatization protocol for the preparation of pyrazolo[1,5-a]pyridines from N-aminopyridines and α,β-unsaturated compounds were developed. The procedure offered multisubstituted pyrazolo[1,5-a]pyridines in good to excellent yield with high and predictable regioselectivity. The modification of marketed drugs including Loratadine, Abiraterone and Metochalcone, a one-pot three-step gram scale synthesis of key intermediate for the preparation of Selpercatinib were demonstrated. Mechanism studies showed that TEMPO served both as a Lewis acid and as an oxidant.

Organic Letters published new progress about [3+2] Cycloaddition reaction (regioselective). 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Safety of 3-(Trifluoromethyl)pyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Trobe, Melanie; Vareka, Martin; Schreiner, Till; Dobrounig, Patrick; Doler, Carina; Holzinger, Ella B.; Steinegger, Andreas; Breinbauer, Rolf published the artcile< A Modular synthesis of teraryl-based α-helix mimetics, part 3: Iodophenyltriflate core fragments featuring side chains of proteinogenic amino acids>, Recommanded Product: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, the main research area is peptidomimetic helix teraryl amino acid synthesis protein interaction inhibitor; Suzuki Miyaura coupling Wittig reaction iodo salicylic aldehyde amination; Inhibitors; Peptide mimetics; Protein–protein interactions; Suzuki coupling; Triflate.

Teraryl-based α-helix mimetics have proven to be useful compounds for the inhibition of protein-protein interactions (PPI). We have developed a modular and flexible approach for the synthesis of teraryl-based α-helix mimetics using a benzene core unit featuring two leaving groups of differentiated reactivity in the Pd-catalyzed cross-coupling used for teraryl assembly. In previous publications we have introduced the methodol. of 4-iodophenyltriflates decorated with the side chains of some of the proteinogenic amino acids. We herein report the core fragments corresponding to the previously missing amino acids Arg, Asn, Asp, Met, Trp and Tyr. Therefore, our set now encompasses all relevant amino acid analogs with the exception of His. In order to be compatible with the triflate moiety, some of the nucleophilic side chains had to be provided in a protected form to serve as stable building blocks. Addnl., cross-coupling procedures for the assembly of teraryls were investigated.

European Journal of Organic Chemistry published new progress about Amination. 329214-79-1 belongs to class pyridine-derivatives, and the molecular formula is C11H16BNO2, Recommanded Product: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Cai, Yuxing; Chen, Jiean; Huang, Yong published the artcile< N-Heterocyclic Carbene-Catalyzed 1,4-Alkylacylation of 1,3-Enynes>, Computed Properties of 350-03-8, the main research area is allenone preparation; enyne aldehyde radical precursor alkylacylation heterocyclic carbene catalyst.

The radical relay coupling reaction recently emerged as a powerful synthetic strategy for producing tetrasubstituted allenes R(R1CHR2)C=C=C(R3)C(O)R4 (R = H, Me; R1 = trifluoromethyl, 1,1-difluoro-2-methoxy-2-oxoethyl, 3-cyanopropyl, etc.; R2 = Me, Ph, thiophen-3-yl, pyridin-3-yl, etc.; R3 = hexyl, cyclopropyl, Ph, 4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)butyl, etc.; R4 = Ph, furan-2-yl, pyridin-3-yl, etc.). However, bond-forming processes involving the allenyl radical intermediate are mostly limited to those promoted by transition metals. In this report, a ketyl radical generated from single-electron oxidation of the Breslow intermediate, which is an excellent coupling partner of allenyl radicals is described. An organocatalytic 1,4-alkylacylation of 1,3-enynes RCH=C(R2)CCR3 occurred smoothly in the presence of an aldehyde R4CHO, a radical precursor, and an N-heterocyclic carbene catalyst. This transformation showed remarkable tolerance to both aromatic and aliphatic aldehydes, enyne substitution, and diversified radical precursors.

Organic Letters published new progress about Acylation. 350-03-8 belongs to class pyridine-derivatives, and the molecular formula is C7H7NO, Computed Properties of 350-03-8.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zheng, Yan-Long; Newman, Stephen G. published the artcile< Methyl Esters as Cross-Coupling Electrophiles: Direct Synthesis of Amide Bonds>, Application In Synthesis of 93-60-7, the main research area is methyl ester amine nickel catalyzed cross coupling amide preparation.

Amide bond formation and transition metal-catalyzed cross-coupling are two of the most frequently used chem. reactions in organic synthesis. Recently, an overlap between these two reaction families was identified when Pd and Ni catalysts were demonstrated to cleave the strong C-O bond present in esters via oxidative addition When simple Me and Et esters are used, this transformation provides a powerful alternative to classical amide bond formations, which commonly feature stoichiometric activating agents. Thus far, few redox-active catalysts have been demonstrated to activate the C(acyl)-O bond of alkyl esters, which makes it difficult to perform informed screening when a challenging reaction needs optimization. We demonstrate that Ni catalysts bearing diverse NHC, phosphine, and nitrogen-containing ligands can all be used to activate Me esters and enable their use in direct amide bond formation.

ACS Catalysis published new progress about Aliphatic esters Role: RCT (Reactant), RACT (Reactant or Reagent). 93-60-7 belongs to class pyridine-derivatives, and the molecular formula is C7H7NO2, Application In Synthesis of 93-60-7.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Blache, Yves; Gueiffier, Alain; Chavignon, Olivier; Viols, Henry; Teulade, Jean Claude; Chapat, Jean Pierre published the artcile< Compared reactivity of 3-, 5-, 6-, and 8-aminoimidazo[1,2-α]pyridines in Combes reaction: access to imidazonaphthyridines and dipyrido[1,2-a:3',2'-d]imidazole>, Application of C6H7N3O2, the main research area is aminoimidazopyridine Combes reaction; imidazonaphthyridine; dipyridoimidazole.

The synthesis of imidazo[1,2-a][1,8]naphthyridines and dipyrido[1,2-a:3′,2′-d]imidazole by treatment of aminoimidazo[1,2-a]pyridines following the Combes procedure is described.

Heterocycles published new progress about 22280-62-2. 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Application of C6H7N3O2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Vijeta, Arjun; Reisner, Erwin published the artcile< Carbon nitride as a heterogeneous visible-light photocatalyst for the Minisci reaction and coupling to H2 production>, Computed Properties of 93-60-7, the main research area is heterogeneous Minisci hydrogen evolution reaction photocatalyst.

Cyanamide functionalized carbon nitride powder is reported as a photocatalyst for direct Minisci-type coupling of heteroarenes with ethers, alcs., and amides using atm. oxygen as the oxidant at room temperature This mild protocol displays broad substrate scope, good functional group tolerance and the catalyst can be easily isolated and reused for several cycles. It thereby addresses the two major limitations of previously reported photoredox-mediated Minisci reactions: (i) use of expensive and potentially harmful non-recyclable photocatalysts, and (ii) requirement of a stoichiometric amount of strong chem. oxidant. Finally, using platinum as a co-catalyst with the carbon nitride allows this light-mediated reaction to generate two value-added products under an anaerobic atm. – functionalized heteroarenes and H2 fuel.

Chemical Communications (Cambridge, United Kingdom) published new progress about Hydrogen evolution reaction catalysts. 93-60-7 belongs to class pyridine-derivatives, and the molecular formula is C7H7NO2, Computed Properties of 93-60-7.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Iddon, Brian; Mack, Arthur G.; Suschitzky, Hans; Taylor, Jack A.; Wakefield, Basil J. published the artcile< Polyhaloaromatic compounds. Part 42. Carbon-13 NMR spectra of polyhalopyridines and 2-pyrimidines>, Synthetic Route of 14121-36-9, the main research area is carbon NMR polyhalo pyridine pyrimidine; substituent effect NMR halopyridine.

13C NMR spectra are reported for 103 polyhalopyridines and 8 polyhalopyrimidines. Substituent effects were calculated and the results used to assign structures.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about NMR (nuclear magnetic resonance). 14121-36-9 belongs to class pyridine-derivatives, and the molecular formula is C5HCl4N, Synthetic Route of 14121-36-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pinkerton, Anthony B.; Sessions, E. Hampton; Hershberger, Paul; Maloney, Patrick R.; Peddibhotla, Satyamaheshwar; Hopf, Meghan; Sergienko, Eduard; Ma, Chen-Ting; Smith, Layton H.; Jackson, Michael R.; Tanaka, Jun; Tsuji, Takashi; Akiu, Mayuko; Cohen, Steven E.; Nakamura, Tsuyoshi; Gardell, Stephen J. published the artcile< Optimization of a urea-containing series of nicotinamide phosphoribosyltransferase (NAMPT) activators>, Reference of 3731-53-1, the main research area is urea nicotinamide phosphoribosyltransferase activator; NAD(+) booster; NAMPT; NAMPT activators; Ureas.

NAD+ is a crucial cellular factor that plays multifaceted roles in wide ranging biol. processes. Low levels of NAD+ have been linked to numerous diseases including metabolic disorders, cardiovascular disease, neurodegeneration, and muscle wasting disorders. A novel strategy to boost NAD+ is to activate nicotinamide phosphoribosyltransferase (NAMPT), the putative rate-limiting step in the NAD+ salvage pathway. We previously showed that NAMPT activators increase NAD+ levels in vitro and in vivo. Herein we describe the optimization of our NAMPT activator prototype (SBI-0797812) leading to the identification of 1-(4-((4-chlorophenyl)sulfonyl)phenyl)-3-(oxazol-5-ylmethyl)urea (34) that showed far more potent NAMPT activation and improved oral bioavailability.

Bioorganic & Medicinal Chemistry Letters published new progress about Cardiovascular disease. 3731-53-1 belongs to class pyridine-derivatives, and the molecular formula is C6H8N2, Reference of 3731-53-1.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Guan, Yanfei; Ingman, Victoria M.; Rooks, Benjamin J.; Wheeler, Steven E. published the artcile< AARON: An Automated Reaction Optimizer for New Catalysts>, Application In Synthesis of 1416819-91-4, the main research area is transition metal catalytic reaction.

We describe an open-source computational toolkit (AARON: An Automated Reaction Optimizer for New catalysts) that automates the quantum mech. geometry optimization and characterization of the transition state and intermediate structures required to predict the activities and selectivities of asym. catalytic reactions. Modern computational quantum chem. has emerged as a powerful tool for explaining the selectivity and activity of asym. catalysts. However, reliably predicting the stereochem. outcome of realistic reactions often requires the geometry optimization of hundreds of transition state and intermediate structures, which is a tedious process. AARON automates these optimizations through an interface with a popular electronic structure package, accelerating quantum chem. workflows to enable the computational screening of potential catalysts. AARON is built using a collection of object-oriented Perl modules (AaronTools) that provide functionality to build and modify mol. and supramol. structures. The main functionalities of AaronTools are also available as stand-alone command-line scripts. The core features of AaronTools and AARON are explained, and representative applications of AARON to both organocatalyzed and transition-metal-catalyzed reactions are presented.

Journal of Chemical Theory and Computation published new progress about Aryl aldehydes Role: PEP (Physical, Engineering or Chemical Process), PROC (Process). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application In Synthesis of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhang, Xiaolong; An, Hualiang; Zhang, Hongqi; Zhao, Xinqiang; Wang, Yanji published the artcile< n-Butyraldehyde Self-Condensation Catalyzed by Sulfonic Acid Functionalized Ionic Liquids>, Synthetic Route of 21876-43-7, the main research area is butyraldehyde self condensation sulfonic acid functionalized ionic liquid catalyst.

Self-condensation of n-butyraldehyde to 2-ethyl-2-hexenal is one of the important processes for the industrial production of 2-ethylhexanol. In the present work, several sulfonic acid functionalized ionic liquids (SFILs) were synthesized. Their acid strengths were determined by the Hammett method combined with UV-vis spectroscopy, and their catalytic performances in n-butyraldehyde self-condensation were investigated. The results show that the conversion of n-butyraldehyde correlated well with the acid strength of the SFILs with the same cation. The SFILs with triethylammonium cations showed a better catalytic performance than those with imidazolium cations or pyridinium cations, and [HSO3-b-N(Et)3]p-TSA (“”b””, butyl) exhibited the highest selectivity. Under the optimal reaction conditions of the mass ratio of [HSO3-b-N(Et)3]p-TSA to n-butyraldehyde = 0.1, reaction temperature = 393 K, and reaction time = 6 h, the conversion of n-butyraldehyde was 89.7% and the selectivity to 2-ethyl-2-hexenal was 87.8%. [HSO3-b-N(Et)3]p-TSA could be reused four times without a significant loss in its catalytic performance. A kinetic anal. result showed that this is a reversible second-order reaction. Compared with the kinetic parameters from the reaction catalyzed by an aqueous base or acid catalyst, the pre-exponential factor is lower due to the restriction of the high viscosity of [HSO3-b-N(Et)3]p-TSA. Finally, a possible reaction mechanism for n-butyraldehyde self-condensation catalyzed by [HSO3-b-N(Et)3]p-TSA was proposed.

Industrial & Engineering Chemistry Research published new progress about Acidity. 21876-43-7 belongs to class pyridine-derivatives, and the molecular formula is C9H13NO3S, Synthetic Route of 21876-43-7.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem