Browse
Submit Data
Databases
API
Help

Dataset Information

24 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Pd/C-mediated synthesis of indoles in water.

ABSTRACT: We describe the utility of a Pd/C-Cu mediated method in the synthesis of 2,5-disubstituted indoles in water via a coupling-cyclization strategy. Further application of this methodology has been demonstrated in the preparation of a target indole derivative via a 7-step process the key step being the Pd/C-mediated coupling reaction.

SUBMITTER: Layek M

PROVIDER: S-EPMC2779661 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Pd/C-mediated synthesis of indoles in water.

Layek Mohosin M Lakshmi Udaya U Kalita Dipak D Barange Deepak Kumar DK Islam Aminul A Mukkanti K K Pal Manojit M

Beilstein journal of organic chemistry 20090923

We describe the utility of a Pd/C-Cu mediated method in the synthesis of 2,5-disubstituted indoles in water via a coupling-cyclization strategy. Further application of this methodology has been demonstrated in the preparation of a target indole derivative via a 7-step process the key step being the Pd/C-mediated coupling reaction. ...[more]

PMID: 19936266

Similar Datasets

Synthesis of 2-Substitued Indoles via Pd-Catalysed Cyclization in an Aqueous Micellar Medium.

Project description:The synthesis of 2-substituted indoles starting from the corresponding unprotected 2-alkynylanilines was made possible in 3% TPGS-750-M water using Pd(OAc)2 alone as the catalyst. The reaction was sensitive to the heating mode respect to the nature of the starting material as, in many cases, convectional heating was better than microwave dielectric heating. The MW (microwave) delivery mode had also an influence in the formation of by-products and, consequently, product yields. A tandem Sonogashira-cyclisation reaction was also accomplished using Pd(OAc)2/Xphos in the nanomicellar water environment.

| S-EPMC8271580 | biostudies-literature

Practical synthesis of indoles and benzofurans in water using a heterogeneous bimetallic catalyst.

Project description:This paper describes the preparation of indoles, azaindoles and benzofurans in pure water by using a new heterogeneous Pd-Cu/C catalyst through a cascade Sonogashira alkynylation-cyclization sequence. Details of the optimization studies and the substrate scope are discussed. This procedure allows the preparation of heterocycles with good yields and is tolerant to a wide variety of functional groups.

| S-EPMC3740569 | biostudies-literature

Synthesis of Indoles and Benzofurans Using a Graphene Oxide-Grafted Aminobisphosphine-Pd<sup>II</sup> Complex.

Project description:Indoles and benzofurans have been synthesized using a graphene oxide-grafted aminobisphosphine-PdII complex (GO@PNP-Pd) under copper-free condition. A range of indole and benzofuran derivatives have been made by the reaction of N-protected 2-iodoanilines and 2-iodophenols with terminal acetylenes in presence of GO@PNP-Pd. The activity of the aminobisphosphine-PdII complex remains the same under both homogeneous and heterogeneous conditions. Finally, the recycling ability of the immobilized catalyst (GO@PNP-Pd) has been examined for five consecutive runs with appreciable conversion.

| S-EPMC6644095 | biostudies-literature

On-DNA Synthesis of Multisubstituted Indoles.

Project description:The increasing role of the DNA-encoded library technology in early phase drug discovery represents a significant demand for DNA-compatible synthetic methods for therapeutically relevant heterocycles. Herein, we report the first on-DNA synthesis of multisubstituted indoles via a cascade reaction of Sonogashira coupling and intramolecular ring closure. Further functionalization by Suzuki coupling at the third position exploits a diverse chemical space. The high fidelity of the method also enabled the construction of an indole-based mock library.

| S-EPMC11002923 | biostudies-literature

Parallel Strategies for the Synthesis of Annulated Pyrido[3,4-b]indoles via Rh(I)- and Pd(0)-Catalyzed Cyclotrimerization.

Project description:Two different pathways for the synthesis of annulated pyrido[3,4-b]indoles are reported using metal-catalyzed cyclotrimerization reactions. A stepwise process using Rh(I)-catalysis in the final step of the synthesis and a multicomponent, tandem catalytic approach using Pd(0)-catalysis both lead to complex nitrogen-containing heterocycles in good yields. Substituent effects are investigated for both pathways, demonstrating that the Pd(0)-catalyzed approach is more sensitive to electron- withdrawing groups.

| S-EPMC6519955 | biostudies-literature

Annulative ?-extension of indoles and pyrroles with diiodobiaryls by Pd catalysis: rapid synthesis of nitrogen-containing polycyclic aromatic compounds.

Project description:A palladium-catalyzed one-step annulative ?-extension (APEX) reaction of indoles and pyrroles that allows rapid access to nitrogen-containing polycyclic aromatic compounds is described. In the presence of palladium pivalate and silver carbonate, diverse indoles or pyrroles coupled with diiodobiaryls in a double direct C-H arylation manner to be transformed into the corresponding ?-extended compounds in a single step. The newly developed catalytic system enables the use of various pyrroles and indoles as templates with a series of diiodobiaryls to provide structurally complicated and largely ?-extended nitrogen-containing polycyclic aromatic compounds that are otherwise difficult to synthesize.

| S-EPMC6180308 | biostudies-literature

Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation.

Project description:We describe herein a Pd-catalyzed methodology for the thioglycoconjugation of iodoaryl peptides and aminoacids. This operationally simple process occurs under semi-aqueous conditions and displays wide substrate scope. The strategy has been successfully applied to both the thioglycosylation of unprotected peptides and the generation of thioglyco-aminoacid building blocks, including those suitable for solid phase peptide synthesis. To demonstrate the broad potential of this technique for late stage functionalization, we successfully incorporated challenging unprotected β-S-GlcNAc- and α-S-GalNAc-derivatives into very long unprotected peptides. This study opens the way to new applications in chemical biology, considering the well-recognized advantages of S-glycosides over O-glycosides in terms of resistance towards both enzymatic and chemical degradation.

| S-EPMC6295873 | biostudies-literature

Synthesis and structure activity relationships of schweinfurthin indoles.

Project description:As part of a program to explore the biological activity of analogues of the natural schweinfurthins, a set of compounds has been prepared where an indole system can be viewed as a substitution for the resorcinol substructure of the schweinfurthin's D-ring. Twelve of these schweinfurthin indoles have been prepared and evaluated in the 60 cell line screen of the National Cancer Institute. While a range of activity has been observed, it is now clear that schweinfurthin indoles can demonstrate the intriguing pattern of activity associated with the natural stilbenes. In the best cases, these indole analogues display both potency and differential activity across the various cell lines comparable to the best resorcinol analogues.

| S-EPMC4030441 | biostudies-literature

A General and Scalable Synthesis of Polysubstituted Indoles.

Project description:A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

| S-EPMC7730962 | biostudies-literature

Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands.

Project description:Palladium-catalyzed aerobic oxidative cross-couplings of indoles and benzene have been achieved by using 4,5-diazafluorene derivatives as ancillary ligands. Proper choice of the neutral and anionic ligands enables control over the reaction regioselectivity.

| S-EPMC3228523 | biostudies-other

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