Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of Heteroannulated Indolopyrazines through Domino N–H Palladium-Catalyzed/Metal-Free Oxidative C–H Bond Activation.

ABSTRACT: A convenient approach to [1,2,5]oxadiazolo[3?,4?:5,6]pyrazino[2,3-b]indoles and their heteroannulated analogues bearing various aryl substituents in the backbone has been developed. This synthetic protocol is based on Pd-catalyzed Buchwald–Hartwig and subsequent annulation by intramolecular oxidative cyclodehydrogenation. The photophysical properties for new polycycles have been measured.

SUBMITTER: Kvashnin YA

PROVIDER: S-EPMC7331205 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Palladium-Catalyzed Oxidative Domino Carbocyclization-Arylation of Bisallenes.

Project description:Herein we report a highly efficient and site-selective palladium-catalyzed oxidative carbocyclization-arylation reaction of bisallenes and arylboronic acids under operationally simple conditions for the selective synthesis of cyclohexadiene derivatives. The palladium source and the solvent proved to be crucial for the selectivity and the reactivity displayed. Interestingly, in the absence of the nucleophile, an oxidative carbocyclization-?-elimination pathway predominates. The reaction conditions are compatible with a wide range of functional groups, and the reaction exhibits broad substrate scope. Furthermore, key information regarding the mechanism was obtained using control experiments and kinetic studies.

| S-EPMC5065722 | biostudies-literature

Total Synthesis of Cyclopiamide A Using Palladium-Catalyzed Domino Cyclization.

Project description:Total synthesis of cyclopiamide A was accomplished using a palladium-catalyzed domino cyclization. Three rings in the tetracyclic skeleton of cyclopiamide A were constructed in a one-step domino reaction incorporating double carbopalladation and C-H activation.

| S-EPMC7660198 | biostudies-literature

Palladium-Catalyzed Domino Aminocarbonylation of Alkynols: Direct and Selective Synthesis of Itaconimides.

Project description:The first direct and selective synthesis of substituted itaconimdes by palladium-catalyzed aminocarbonylation of alkynols is reported. Key to the success of this transformation is the use of a novel catalyst system involving ligand L11 and appropriate reaction conditions. In the protocol here presented, easily available propargylic alcohols react with N-nucleophiles including aryl- and alkylamines as well as aryl hydrazines to provide a broad variety of interesting heterocycles with high catalyst activity and excellent selectivity. The synthetic utility of the protocol is demonstrated in the synthesis of natural product 11 with aminocarbonylation as the key step. Mechanistic studies and control experiments reveal the crucial role of the hydroxyl group in the substrate for the control of selectivity.

| S-EPMC8397365 | biostudies-literature

Synthesis of Cross-Conjugated Polyenes via Palladium-Catalyzed Oxidative C-C Bond Forming Cascade Reactions of Allenes.

Project description:An efficient palladium-catalyzed oxidative C-C bond forming cascade reaction of allenes involving a coupling between an enallene and an allenyne followed by a carbocyclization of the generated Pd-intermediate was developed. This cascade reaction afforded functionalized cross-conjugated polyenes. The enallene is initially activated by palladium and reacts with the allenyne to give the cross-conjugated polyenes.

| S-EPMC7311062 | biostudies-literature

Palladium-Catalyzed Oxidative Synthesis of ?-Acetoxylated Enones from Alkynes.

Project description:We report a palladium-catalyzed oxidative functionalization of alkynes to generate ?-acetoxylated enones in one step. A range of functional groups are well-tolerated in this reaction. Mechanistic studies, including the use of (18) O-labeled DMSO, revealed that the ketone oxygen atom in the product originates from DMSO.

| S-EPMC5021131 | biostudies-other

Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles.

Project description:This paper describes a phosphine-free palladium-catalyzed method for direct C-arylation of free (N-H)-indoles and pyrroles with iodo- and bromoarene donors. Employing commercially available materials, this new and operationally simple procedure provides a rapid entry to a wide range of C-arylated (N-H)-indoles including derivatives of tryptamine. In the course of this study, a profound halide effect was uncovered, affecting both the efficiency and regioselectivity of indole arylation.

| S-EPMC2971669 | biostudies-literature

Modular synthesis of dihydro-isoquinolines: palladium-catalyzed sequential C(sp2)-H and C(sp3)-H bond activation.

Project description:An efficient synthesis of dihydro-isoquinolines via a Pd-catalyzed double C-H bond [a C(sp2)-H and a C(sp3)-H bond] activation/annulation (CHAA) reaction is presented. This methodology features a short reaction time, high atom economy (loss of H2O only) and the formation of a sterically less favoured tertiary C-N bond. This fast (30 min) and environmentally benign radical C-H activation approach has demonstrated the potential direction for the future design/development of fast and efficient C-H direct functionalization processes.

| S-EPMC5950195 | biostudies-other

A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction.

Project description:Herein we report a novel palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, ortho-bromobenzoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes ortho-C-H activation, decarbonylation and subsequent a retro-Diels-Alder process. Pleasantly, this protocol has a wider substrate range, shorter reaction times and higher yields of products than previously reported methods.

| S-EPMC6369988 | biostudies-literature

Continuous-Flow Synthesis and Derivatization of Aziridines through Palladium-Catalyzed C(sp(3) )-H Activation.

Project description:A continuous-flow synthesis of aziridines by palladium-catalyzed C(sp(3) )-H activation is described. The new flow reaction could be combined with an aziridine-ring-opening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was developed and used to design the C-H activation flow process and illustrates an approach towards first-principles design based on novel catalytic reactions.

| S-EPMC5094502 | biostudies-literature

Synthesis of Unsymmetrical 2,6-Diarylanilines by Palladium-Catalyzed C-H Bond Functionalization Methodology.

Project description:3,5-Dimethylpyrazole was employed as a monodentate directing group for palladium-catalyzed ortho-sp2 C-H arylation with aryl iodides. The reaction shows good functional group tolerance and outstanding selectivity for mono- ortho-arylation. Ozonolysis of ortho-arylated arylpyrazoles gave acylated biphenylamines that were further arylated to afford unsymmetrically substituted 2,6-diarylacetanilides.

| S-EPMC6013069 | 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