Browse
Submit Data
Databases
API
Help

Dataset Information

28 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Bronsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans.

ABSTRACT: Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans has been developed. This method operates via the in situ formation of aminobenzylfuran, followed by its recyclization into the indole core. The method proved to be efficient for substrates possessing different functional groups, including -OMe, -CO2Cy, and -Br. The resulting indoles can easily be transformed into diverse scaffolds, including 2,3- and 1,2-fused indoles, and indoles possessing an ?,?-unsaturated ketone moiety at the C-2 position.

SUBMITTER: Kuznetsov A

PROVIDER: S-EPMC3923594 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans.

Kuznetsov Alexey A Makarov Anton A Rubtsov Aleksandr E AE Butin Alexander V AV Gevorgyan Vladimir V

The Journal of organic chemistry 20131120 23

Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans has been developed. This method operates via the in situ formation of aminobenzylfuran, followed by its recyclization into the indole core. The method proved to be efficient for substrates possessing different functional groups, including -OMe, -CO2Cy, and -Br. The resulting indoles can easily be transformed into diverse scaffolds, including 2,3- and 1,2-fused indoles, and indoles possessing an α,β-unsatu ...[more]

PMID: 24255969

Similar Datasets

One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines.

Project description:The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-substituted-3-alkynylindoles. The reaction can be applied to unprotected anilines, was tolerant to functional groups and easy to carry out (RT, and requires neither an inert atmosphere nor special solvents).

| S-EPMC3107533 | biostudies-literature

Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Bronsted acid catalyzed asymmetric allenylboration reactions.

Project description:Chiral Brønsted acid catalyzed asymmetric allenylboration reactions are described. Under optimized conditions, anti-homopropargyl alcohols 2 are obtained in high yields with excellent diastereo- and enantioselectivities from stereochemically matched aldehyde allenylboration reactions with (M)-1 catalyzed by the chiral phosphoric acid (S)-4. The syn-isomers 3 can also be obtained in good diastereoselectivities and excellent enantioselectivities from the mismatched allenylboration reactions of aromatic aldehydes using (M)-1 in the presence of the enantiomeric phosphoric acid (R)-4. The stereochemistry of the methyl group introduced into 2 and 3 is controlled by the chirality of the allenylboronate (M)-1, whereas the configuration of the new hydroxyl stereocenter is controlled by the enantioselectivity of the chiral phosphoric acid catalyst used in these reactions. The synthetic utility of this methodology was further demonstrated in highly diastereoselective syntheses of a variety of anti, anti-stereotriads, the direct synthesis of which has constituted a significant challenge using previous generations of aldol and crotylmetal reagents.

| S-EPMC3474359 | biostudies-literature

Highly Enantioselective One-Pot Synthesis of Chiral β-Heterosubstituted Alcohols via Ruthenium-Prolinamide-Catalyzed Asymmetric Transfer Hydrogenation.

Project description:The utility of a chiral Ru-prolinamide catalytic system has been demonstrated in one-pot synthesis of optically active β-triazolylethanol and β-hydroxy sulfone derivatives. The said methodology proceeds through asymmetric transfer hydrogenation of in situ formed ketones of the corresponding chiral products. Various chiral prolinamide ligands were screened, and ligand L6 with isopropyl groups substituted at the ortho position has shown excellent activity at 60 °C in aqueous medium producing up to 95% yield and 99.9% enantioselectivity.

| S-EPMC6644779 | biostudies-literature

Chiral Bronsted acid catalyzed enantioselective synthesis of anti-homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates.

Project description:A chiral phosphoric acid catalyzed kinetic resolution/allenylboration of racemic allenylboronates with aldehydes is described. Allenylboration of aldehydes with 2.8 equiv of allenylboronate (±)-1 in the presence of 10 mol % of catalyst (R)-2 provided anti-homopropargyl alcohols 3 in 83-95% yield with 9:1 to 20:1 diastereoselectivity and 73-95% ee. The catalyst enables the kinetic resolution of the racemic allenylboronate (±)-1 to set the methyl stereocenter and biases the facial attack of the aldehyde to set the stereochemistry of the hydroxyl group in 3.

| S-EPMC3640598 | biostudies-literature

One-pot synthesis of epoxides from benzyl alcohols and aldehydes.

Project description:A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey-Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes.

| S-EPMC6142752 | biostudies-literature

Bronsted Acid-Mediated Domino One-Pot Dual C-C Bond Formation: Chemoselective Synthesis of Fused Tricyclic Ketones.

Project description:A chemoselective synthesis of fused novel tricyclic motifs via a facile domino intramolecular cyclization is presented. The strategy enables the formation of dual C-C bond via intramolecular Friedel-Crafts alkylation followed by acylation to accomplish fused tricyclic ketones. Significantly, these fused tricyclic compounds are ubiquitous and constitute major structural cores of natural products.

| S-EPMC6641420 | biostudies-literature

Lewis Base-Bronsted Acid-Enzyme Catalysis in Enantioselective Multistep One-Pot Syntheses.

Project description:Establishing one-pot, multi-step protocols combining different types of catalysts is one important goal for increasing efficiency in modern organic synthesis. In particular, the high potential of biocatalysts still needs to be harvested. Based on an in-depth mechanistic investigation of a new organocatalytic protocol employing two catalysts {1,4-diazabicyclo[2.2.2]octane (DABCO); benzoic acid (BzOH)}, a sequence was established providing starting materials for enzymatic refinement (ene reductase; alcohol dehydrogenase): A gram-scale access to a variety of enantiopure key building blocks for natural product syntheses was enabled utilizing up to six catalytic steps within the same reaction vessel.

| S-EPMC8360128 | biostudies-literature

One-Pot Synthesis of 5-Hydroxymethylfurfural from Glucose by Bronsted Acid-Free Bifunctional Porous Coordination Polymers in Water.

Project description:Efficient synthesis of 5-hydroxymethylfurfural (HMF) using glucose (Glc) as a starting material represents an important process in biomass transformation. In this study, novel bifunctional porous coordination polymer (PCP) catalysts [PCP(Cr)-NH2-x (CH3) x ; x = 0, 1, or 2] containing Lewis acidic and Lewis basic sites have been synthesized and utilized as solid-phase catalysts for HMF synthesis starting from a Glc-in-water system. PCP(Cr)-NH2 was found as the optimal catalyst, with an HMF yield of 65.9% and Glc conversion of 99.9% in a water/tetrahydrofuran (THF) system. Compared with PCP(Cr), amino groups in PCP(Cr)-NH2 catalysts play a vital role in Glc isomerization and subsequent dehydration-cyclization process to obtain the highly selective and effective fructose-to-HMF conversion. High yield and chemoselectivity are ascribed to concurrent extraction of HMF into the THF layer just upon its formation in water. The mechanism of Lewis acid-base synergistic catalysis was deduced by means of infrared spectroscopy, and catalysts could be reused after simple washing procedure with high reproducibility.

| S-EPMC6648545 | biostudies-literature

Highly stereoselective Bronsted acid catalyzed synthesis of spirooxindole pyrans.

Project description:A Brønsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a ?-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones.

| S-EPMC3115630 | biostudies-literature

One-pot synthesis of polysubstituted indoles from aliphatic nitro compounds under mild conditions.

Project description:Polysubstituted indoles can be prepared directly from functionalized nitroalkanes under very mildly acidic conditions in a simple, one-pot, two-stage procedure.

| S-EPMC1855094 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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