Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of macroheterocycles through intramolecular oxidative coupling of furanoid β-ketoesters.

ABSTRACT:

SUBMITTER: Nicolaou KC

PROVIDER: S-EPMC3348726 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of macroheterocycles through intramolecular oxidative coupling of furanoid β-ketoesters.

Nicolaou K C KC Hale Christopher R H CR Ebner Christian C Nilewski Christian C Ahles Christopher F CF Rhoades Derek D

Angewandte Chemie (International ed. in English) 20120405 19

PMID: 22489095

Similar Datasets

Nickel catalyzed intramolecular oxidative coupling: synthesis of 3-aryl benzofurans.

Project description:Recent research has been focused on the transition metal-catalyzed reactions. Herein we have developed nickel-catalyzed synthesis of 3-aryl benzofurans from ortho-alkenyl phenols via intramolecular dehydrogenative coupling. Notably, simple O2 gas served as an oxidant, without using any sacrificial hydrogen acceptor. The strategy enabled the synthesis of 3-aryl benzofurans in good to excellent yields.

| S-EPMC9054549 | biostudies-literature

Intramolecular Umpolung Synthesis of Exocyclic β-Amino Alcohols through Decarboxylative Amination.

Project description:An intramolecular aminative Umpolung cyclization strategy has been developed by using α,α-diphenylglycine (2) as the amination and Umpolung reagent. Aldehydes (1) bearing an additional carbonyl group underwent condensation with α,α-diphenylglycine to form an imine, decarboxylation to generate a delocalized 2-azaallylanion, and subsequent intramolecular Umpolung cyclization to produce a variety of exocyclic β-amino alcohols (6) in 60-93% yields with up to >20:1 trans/cis selectivity under mild conditions.

| S-EPMC6644024 | biostudies-literature

Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols.

Project description:Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.

| S-EPMC6581424 | biostudies-literature

Radical coupling of <i>β</i>-ketoesters and amides promoted by Bronsted/Lewis acids.

Project description:Recent advances in photocatalysis have enabled radical methods with complementary chemoselectivity to established two electron bond forming approaches. While this radical strategy has previously been limited to substrates with favorable redox potentials, Brønsted/Lewis acid activation has emerged as a means of facilitating otherwise difficult reductions. We report herein our investigations into the Lewis acid-promoted redox activation of β-ketocarbonyls in a model photocatalytic radical alkylation reaction. Rapid evaluation of substrates and reactions conditions was achieved by high throughput experimentation using 96-well plate photoreactors.

| S-EPMC8411943 | biostudies-literature

Probing intramolecular vibronic coupling through vibronic-state imaging.

Project description:Vibronic coupling is a central issue in molecular spectroscopy. Here we investigate vibronic coupling within a single pentacene molecule in real space by imaging the spatial distribution of single-molecule electroluminescence via highly localized excitation of tunneling electrons in a controlled plasmonic junction. The observed two-spot orientation for certain vibronic-state imaging is found to be evidently different from the purely electronic 0-0 transition, rotated by 90°, which reflects the change in the transition dipole orientation from along the molecular short axis to the long axis. Such a change reveals the occurrence of strong vibronic coupling associated with a large Herzberg-Teller contribution, going beyond the conventional Franck-Condon picture. The emergence of large vibration-induced transition charges oscillating along the long axis is found to originate from the strong dynamic perturbation of the anti-symmetric vibration on those carbon atoms with large transition density populations during electronic transitions.

| S-EPMC7904785 | biostudies-literature

Selective one-pot synthesis of allenyl and alkynyl esters from beta-ketoesters.

Project description:A convenient method is described for the dehydration of beta-ketoesters to generate conjugated and deconjugated alkynyl esters and conjugated allenyl esters. This sequential one-pot method involves the formation of a vinyl triflate monoanion intermediate that leads to the selective formation of alkynes or allenes depending on additives and conditions used. Product outcomes appear to be a function of unique mono- and dianion mechanisms which are described.

| S-EPMC2652892 | biostudies-literature

Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride.

Project description:Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based "click chemistry" is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.

| S-EPMC6676414 | biostudies-literature

Synthesis of Asthma Drug Zafirlukast (Accolate) Using Intramolecular Oxidative Coupling via sp<sup>3</sup> C-H Bond Activation.

Project description:The FDA-approved drug for the treatment of asthma, zafirlukast, is synthesized engaging multiple catalytic reactions including a new method for the construction of 3-aroylindoles via oxidative cyclization. The highlights include transition-metal and peroxide free C-H bond activation using the stoichiometric amount of sodium persulfate as an oxidizing agent in the construction of 3-aroylindole, avoiding transition metal, with over 28% overall yield. The complete process has a turnaround time of 28 h to get the target molecule starting from substituted aniline, with practically no protecting groups.

| S-EPMC6641481 | biostudies-literature

Hypervalent iodine(III)-promoted intermolecular C-C coupling of vindoline with β-ketoesters and related substrates.

Project description:The regioselective intermolecular coupling reaction of vindoline with a wide range of substrates including β-ketoesters, β-diketones, β-ketoaldehydes, β-ketonitriles, malononitriles, and β-cyanoesters provides an opportunity for the synthesis of vinblastine analogues containing deep-seated changes in the upper velbanamine subunit. The transition-metal-free hypervalent iodine(III)-promoted intermolecular sp(3)/sp(2) coupling, representing a special class of selective C-H activation with direct carbon-carbon bond formation, proceeds with generation of a quaternary center capable of incorporation of the vinblastine C16' methyl ester and functionalized for subsequent divergent heterocycle introduction.

| S-EPMC3607625 | biostudies-literature

Intramolecular anodic olefin coupling reactions and the synthesis of cyclic amines.

Project description:Anodic olefin coupling reactions using a tosylamine trapping group have been studied. The cyclizations are favored by the use of a less-polar radical cation and more basic reaction conditions. The most significant factor for obtaining good yields of cyclic product is the use of the more basic reaction conditions. However, a number of factors including the nature of both the solvent and the electrolyte used can influence the yield of the cyclizations. The cyclizations allow for the rapid synthesis of both substituted proline and pipecolic acid type derivatives.

| S-EPMC3950632 | 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