Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Ruthenium-catalyzed, site-selective C-H activation: access to C5-substituted azaflavanone.

ABSTRACT: A site-selective ruthenium-catalyzed keto group assisted C-H bond activation of 2-aryl tetrahydroquinoline (azaflavanone) derivatives has been achieved with a variety of alkenes for the first time. A wide range of substrates was utilized for the synthesis of a wide variety of alkenylated azaflavanones. This simple and efficient protocol provides the C5-substituted azaflavanone derivatives in high yields with a broad range of functional group tolerance. Further, the C5-alkenylated products were converted into substituted 2-aryl quinoline derivatives in good yields.

SUBMITTER: Bakthadoss M

PROVIDER: S-EPMC9056431 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Ruthenium-catalyzed, site-selective C-H activation: access to C5-substituted azaflavanone.

Bakthadoss Manickam M Reddy Tadiparthi Thirupathi TT Sharada Duddu S DS

RSC advances 20200826 52

A site-selective ruthenium-catalyzed keto group assisted C-H bond activation of 2-aryl tetrahydroquinoline (azaflavanone) derivatives has been achieved with a variety of alkenes for the first time. A wide range of substrates was utilized for the synthesis of a wide variety of alkenylated azaflavanones. This simple and efficient protocol provides the C5-substituted azaflavanone derivatives in high yields with a broad range of functional group tolerance. Further, the C5-alkenylated products were c ...[more]

PMID: 35520642

Similar Datasets

Ruthenium-Catalyzed Site-Selective Trifluoromethylations and (Per)Fluoroalkylations of Anilines and Indoles.

Project description:Introducing (per)fluoroalkyl groups into arenes continues to be an interesting, but challenging area in organofluorine chemistry. We herein report an ortho-selective C-H perfluoroalkylation including trifluoromethylations of anilines and indoles without the need of protecting groups using Rf I and Rf Br as commercially available reagents. The availability and price of the starting materials and the inherent selectivity make this novel methodology attractive for the synthesis of diverse (per)fluoroalkylated building blocks, for example, for bioactive compounds and materials.

| S-EPMC7317475 | biostudies-literature

Ruthenium-Catalyzed meta-Selective C-H Bromination.

Project description:The first example of a transition-metal-catalyzed, meta-selective C-H bromination procedure is reported. In the presence of catalytic [{Ru(p-cymene)Cl2 }2 ], tetrabutylammonium tribromide can be used to functionalize the meta C-H bond of 2-phenylpyridine derivatives, thus affording difficult to access products which are highly predisposed to further derivatization. We demonstrate this utility with one-pot bromination/arylation and bromination/alkenylation procedures to deliver meta-arylated and meta-alkenylated products, respectively, in a single step.

| S-EPMC4678425 | biostudies-literature

Stereoselective access to Z and E macrocycles by ruthenium-catalyzed Z-selective ring-closing metathesis and ethenolysis.

Project description:The first report of Z-selective macrocyclizations using a ruthenium-based metathesis catalyst is described. The selectivity for Z macrocycles is consistently high for a diverse set of substrates with a variety of functional groups and ring sizes. The same catalyst was also employed for the Z-selective ethenolysis of a mixture of E and Z macrocycles, providing the pure E isomer. Notably, an ethylene pressure of only 1 atm was required. These methodologies were successfully applied to the construction of several olfactory macrocycles as well as the formal total synthesis of the cytotoxic alkaloid motuporamine C.

| S-EPMC3561906 | biostudies-literature

Ruthenium(ii)-catalyzed regioselective direct C4- and C5-diamidation of indoles and mechanistic studies.

Project description:A ruthenium(ii)-catalyzed regioselective direct diamidation of 3-carbonylindoles at the C4- and C5-positions using various dioxazolones is described. This novel protocol allows for the effective installation of two amide groups on the benzene ring in indole. A remarkably broad substrate scope, excellent functional group tolerance, and mild reaction conditions are notable features of this protocol. Further explorations reveal that benzo[b]thiophene-3-carboxaldehyde is a viable substrate and affords its corresponding diamidation products. The diamido indoles are further converted into various functionalized products and used as sensors for metal ion detection. Density functional theory studies are also conducted to propose a reaction mechanism and provide a detailed understanding of the regioselectivity observed in the reaction.

| S-EPMC8409494 | biostudies-literature

Ruthenium-Catalyzed Carbocycle-Selective Hydrogenation of Fused Heteroarenes.

Project description:The homogeneous catalytic hydrogenation of benzo-fused heteroarenes generally provides partially hydrogenated products wherein the heteroaryl ring is preferentially reduced, such as quinoline hydrogenation, leading to 1,2,3,4-tetrahydroquinoline. Herein, we report a carbocycle-selective hydrogenation of fused N-heteroarenes (quinoline, isoquinoline, quinoxaline, etc.) using the Ru complex of a chiral spiroketal-based diphosphine (SKP) as the catalyst, affording the corresponding 5,6,7,8-tetrahydro products in high chemoselectivities. This catalytic system is also effective for the asymmetric carbocycle hydrogenation of fused heteroarenes bearing a boryl or amino group. Experimental studies provided a strong support for the homogeneous nature of the catalysis, and an inner-sphere mechanism was proposed for the hydrogenation. DFT calculations indicated that the hydrogenation is initiated by η4-coordinative activation of quinoline carbocycle to Ru dihydride complex of SKP, followed by metal-to-ligand hydride transfer. Subsequent carbocycle reduction proceeds via consecutive steps of the H2 oxidative addition and C-H reductive elimination.

| S-EPMC11673584 | biostudies-literature

Ruthenium-catalyzed C-H activation of thioxanthones.

Project description:Thioxanthones - being readily available in one step from thiosalicylic acid and arenes - were used in ruthenium-catalyzed C-H-activation reaction to produce 1-mono- or 1,8-disubstituted thioxanthones in good to excellent yields. Scope and limitation of this reaction are presented.

| S-EPMC4419513 | biostudies-literature

Alkene chemoselectivity in ruthenium-catalyzed Z-selective olefin metathesis.

Project description: Not available

| S-EPMC3826562 | biostudies-literature

Ruthenium-catalyzed C-H bond activation and annulation of phenothiazine-3-carbaldehydes: facile access to dual-emission materials.

Project description:Reported herein is the first example of a ruthenium-catalyzed C-H activation/annulation of phenothiazine-3-carbaldehydes to construct structurally diverse pyrido[3,4-c]phenothiazin-3-iums with dual-emission characteristics. Novel organic single-molecule white-light materials based on pyrido[3,4-c]phenothiazin-3-iums with dual-emission and thermally activated delayed fluorescence (TADF) characteristics have been developed for the first time herein. Furthermore, the dual-emission molecule could be fabricated as water-dispersed NPs, which could be applied in two-channel emission intensity ratio imaging to observe the intercellular structure and can specifically target the cell membrane.

| S-EPMC11740230 | biostudies-literature

Palladium-Catalyzed Site-Selective Regiodivergent Carbocyclization of Di- and Trienallenes: A Switch between Substituted Cyclohexene and Cyclobutene.

Project description:Nature efficiently produces a myriad of structurally diverse carbon ring frameworks from common linear precursors via cyclization reactions at specific olefinic sites in dienes or polyenes. In contrast, achieving the site-selective functionalization of diene or polyene substrates remains a formidable challenge in chemical synthesis. Herein, we report a pair of highly site-selective, regiodivergent carbocyclization reactions of dienallenes and trienallenes, enabling the efficient synthesis of cis-1,4-disubstituted cyclohexenes and trans-1,2-disubstituted cyclobutenes from a common precursor with high diastereoselectivity. Remarkably, simple achiral organophosphoric acids and amines are identified as powerful ligands for controlling these palladium-catalyzed regiodivergent carbocyclizations. This approach represents the first example of site-selective regiodivergent carbocyclization, providing a practical method for the stereospecific synthesis of thermodynamically disfavored cis-1,4-disubstituted cyclohexenes and fully substituted trans-1,2-cyclobutenes. Additionally, the methodology developed offers general insights into the development of metal-catalyzed site-selective, regiodivergent carbocyclizations of diene and polyene precursors, mimicking natural carbocyclization processes.

| S-EPMC11926882 | biostudies-literature

Stereo- and Site-Selective Crotylation of Alcohol Proelectrophiles via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by Methylallene and Butadiene.

Project description:Iodide-bound ruthenium-JOSIPHOS complexes catalyze the redox-neutral C-C coupling of primary alcohols with methylallene (1,2-butadiene) or 1,3-butadiene to form products of anti-crotylation with good to excellent levels of diastereo- and enantioselectivity. Distinct from other methods, direct crotylation of primary alcohols in the presence of unprotected secondary alcohols is possible, enabling generation of spirastrellolide B (C9-C15) and leucascandrolide A (C9-C15) substructures in significantly fewer steps than previously possible.

| S-EPMC9712268 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data