Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions.

ABSTRACT: An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki-Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.

SUBMITTER: Hrizi A

PROVIDER: S-EPMC8434198 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Synthesis of Highly Functionalized Decalins via Metallacycle-Mediated Cross-Coupling.

Project description:Bridged bicyclic metallacyclopentenes generated from the [4 + 2] cycloaddition of metallacyclopentadienes with alkenes have been proposed as reactive intermediates in the course of [2 + 2 + 2] annulation reactions. Recently a collection of alkoxide-directed Ti-mediated [2 + 2 + 2] annulation reactions have been discovered for the synthesis of densely functionalized hydrindanes, where the bridged bicyclic metallacyclopentenes from intramolecular [4 + 2] were treated as fleeting intermediates en route to cyclohexadiene products formed by formal cheletropic extrusion of Ti(Oi-Pr)2. In studies aimed at understanding the course of these organometallic cascade reactions it was later discovered that these bridged bicyclic intermediates can be trapped by various elimination processes. Here, we have realized metallacycle-mediated annulation reactions for the assembly of angularly substituted decalins--structural motifs that are ubiquitous in natural products and molecules of pharmaceutical relevance. In addition to defining the basic annulation reaction we have discovered a surprising stability associated with the complex organometallic intermediates generated in the course of this coupling process and document here the ability to control the fate of such species. Ligand-induced cheletropic extrusion of the titanium center delivers cyclohexadiene-containing products, while several distinct protonation events have been identified to realize polycyclic products that contain three new stereocenters (one of which is the angular quaternary center that is a hallmark of alkoxide-directed titanium-mediated [2 + 2 + 2] annulation reactions). Examples of this metallacycle-mediated annulation reaction are provided to demonstrate that a range of stereodefined fused bicyclo[4.4.0]decanes are accessible, including those that contain aromatic and aliphatic substituents, and an empirical model is presented to accompany the observations made.

| S-EPMC4882187 | biostudies-literature

Palladium-catalyzed coupling reactions on functionalized 2-trifluoromethyl-4-chromenone scaffolds. Synthesis of highly functionalized trifluoromethyl-heterocycles.

Project description:The chromenone core is a ubiquitous group in biologically-active natural products and has been extensively used in organic synthesis. Fluorine derived compounds, including those with a trifluoromethyl group (-CF3), have shown enhanced biological activities in numerous pharmaceuticals compared with their non-fluorinated analogs. We have found that 2-trifluoromethyl chromenones can be readily functionalized in the 8- and 7-positions, providing chromenones cores of high structural complexity which are excellent precursors for numerous trifluoromethyl-heterocycles.

| S-EPMC6605783 | biostudies-literature

Towards a facile and convenient synthesis of highly functionalized indole derivatives based on multi-component reactions.

Project description:A library of potentially bioactive compounds through the novel 1H-indole-methyl-isocyanide and MCRs has been described. A flexible and efficient synthesis affording great complexity and diversity is achieved with moderate to good yields with no need for protection and deprotection steps.

| S-EPMC4015188 | biostudies-literature

Highly substituted indole library synthesis by palladium-catalyzed coupling reactions in solution and on a solid support.

Project description:3-Iodoindoles have been synthesized by the iodocyclization of N,N-dialkyl-o-(1-alkynyl)anilines, obtained by the Pd/Cu catalyzed coupling of terminal acetylenes with N,N-dialkyl-o-iodoanilines. These 3-iodoindoles undergo palladium-catalyzed Sonogashira and Suzuki coupling reactions to yield 1,2,3-trisubstituted indoles. These reactions have been applied to parallel library synthesis utilizing commercially available terminal acetylenes and boronic acids. The aforementioned chemistry has also been carried out on a chlorinated Wang resin as a solid support, affording 1,2,3,5-tetrasubstituted indoles after cleavage from the support. A diverse 42-member library of highly substituted indoles has been synthesized.

| S-EPMC2760449 | biostudies-literature

Simple synthesis of pyrrolo[3,2-e]indole-1-carbonitriles.

Project description:Alkylation of 5-nitroindol-4-ylacetonitriles with ethyl chloroacetate, ?-halomethyl ketones, and chloroacetonitrile followed by a treatment of the products with chlorotrimethylsilane in the presence of DBU gives 1-cyanopyrrolo[3,2-e]indoles substituted in position 2 with electron-withdrawing groups.

| S-EPMC3678543 | biostudies-literature

Synthesis of Diarylated 4-Pyridylmethyl Ethers via Palladium-Catalyzed Cross-Coupling Reactions.

Project description:The direct arylation of weakly acidic sp3-hybridized C-H bonds via deprotonated cross-coupling processes (DCCP) is a challenge. Herein, a Pd(NIXANTPHOS)-based catalyst for the mono arylation of 4-pyridylmethyl 2-aryl ethers to generate diarylated 4-pyridyl methyl ethers is introduced. Furthermore, under similar conditions, the diarylation of 4-pyridylmethyl ethers with aryl bromides has been developed. These methods enable the synthesis of new pyridine derivatives, which are common in medicinally active compounds and in application in materials science.

| S-EPMC5722243 | biostudies-literature

Synthesis of unsymmetrical diarylureas via Pd-catalyzed C-N cross-coupling reactions.

Project description:A facile synthesis of unsymmetrical N,N'-diarylureas is described. The utilization of the Pd-catalyzed arylation of ureas enables the synthesis of an array of diarylureas in good to excellent yields from benzylurea via a one-pot arylation-deprotection protocol, followed by a second arylation.

| S-EPMC3127456 | biostudies-literature

Three-Component One-Pot Synthesis of Highly Functionalized Bis-Indole Derivatives.

Project description:In this study, we detail the development of a concise and efficient three-component protocol for the regioselective synthesis of highly functionalized bis-indoles through a one-pot, two-step sequential process starting from enaminones 1, indoles 2, and acenaphthylene-1,2-dione 3 that is catalyzed by piperidine and p-methyl benzenesulfonic acid. This protocol has several advantages including simplicity of experimental operation, high efficiency of bond formation, ready availability and low cost of starting materials, environmentally benign conditions, and target molecular diversity.

| S-EPMC6682060 | biostudies-literature

Stereoselective synthesis of highly functionalized alpha-diazo-beta-ketoalkanoates via catalytic one-pot Mukaiyama-Aldol reactions.

Project description:Methyl diazoacetoacetate undergoes zinc triflate catalyzed condensation with a broad selection of aldehydes to produce delta-siloxy-alpha-diazo-beta-ketoalkanoates in good yield, and delta-hydroxy-alpha-diazo-beta-ketoalkanoates are formed with high diastereoselectivity in reactions with alpha-diazo-beta-ketopentanoate promoted by dibutylboron triflate.

| S-EPMC2829718 | biostudies-literature

Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling.

Project description:An efficient total synthesis of the annulated indole natural product (±)-cis-trikentrin B was accomplished by means of a regioselectively generated 6,7-indole aryne cycloaddition via selective metal-halogen exchange from a 5,6,7-tribromoindole. The unaffected C-5 bromine was subsequently used for a Stille cross-coupling to install the butenyl side chain and complete the synthesis. This strategy provides rapid access into the trikentrins and the related herbindoles, and represents another application of this methodology to natural products total synthesis. The required 5,6,7-indole aryne precursor was prepared using the Leimgruber-Batcho indole synthesis.

| S-EPMC4179867 | 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