Browse
Submit Data
Databases
API
Help

Dataset Information

26 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Parallel synthesis of a multi-substituted benzo[b]furan library.

ABSTRACT: The solution-phase parallel synthesis of a 121-member library of multi-substituted benzo[ b]furans is described. 2,3,5-Trisubstituted benzo[ b]furans have been prepared by the palladium-catalyzed substitution of 3-iodobenzofurans by Suzuki-Miyaura, carbonylative Suzuki, Sonogashira, Heck, and carboalkoxylation chemistry. The 3-iodobenzofurans are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization with ICl.

SUBMITTER: Cho CH

PROVIDER: S-EPMC2669318 | biostudies-literature | 2008 Nov-Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Parallel synthesis of a multi-substituted benzo[b]furan library.

Cho Chul-Hee CH Neuenswander Benjamin B Lushington Gerald H GH Larock Richard C RC

Journal of combinatorial chemistry 20081021 6

The solution-phase parallel synthesis of a 121-member library of multi-substituted benzo[ b]furans is described. 2,3,5-Trisubstituted benzo[ b]furans have been prepared by the palladium-catalyzed substitution of 3-iodobenzofurans by Suzuki-Miyaura, carbonylative Suzuki, Sonogashira, Heck, and carboalkoxylation chemistry. The 3-iodobenzofurans are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed ...[more]

PMID: 18937516

Similar Datasets

Solution-phase parallel synthesis of a multi-substituted benzo[b]thiophene library.

Project description:Generation of a library using parallel syntheses of multi-substituted benzo[b]thiophenes is described. The requisite 3-iodobenzo[b]thiophenes are readily prepared in excellent yields from various alkynes bearing electron-rich aromatic rings by electrophilic cyclization using I(2) in CH(2)Cl(2). The heteroaromatic carbon-iodine bonds allow further diversification by palladium-catalyzed Suzuki-Miyaura, Sonogashira, Heck, and carboalkoxylation chemistry to give multi-substituted benzo[b]thiophene derivatives.

| S-EPMC2743771 | biostudies-literature

Solution-phase synthesis of a highly substituted furan library.

Project description:A library of furans has been synthesized by iodocyclization and further diversified by palladium-catalyzed coupling processes. The key intermediate 3-iodofurans have been prepared by the electrophilic iodocyclization of 2-iodo-2-alken-1-ones in the presence of various nucleophiles in good to excellent yields under mild reaction conditions. These 3-iodofurans are the key components for library generation through subsequent elaboration by palladium-catalyzed processes, such as Suzuki-Miyaura, Sonagashira, Heck, aminocarbonylation, and carboalkoxylation chemistry to afford a diverse set of 2,3,4,5-tetrasubstituted furans.

| S-EPMC3437248 | biostudies-literature

Highly substituted lactone/ester-containing furan library by the palladium-catalyzed carbonylation of hydroxyl-substituted 3-iodofurans.

Project description:Highly substituted lactone- and ester-containing furans have been prepared by the efficient palladium-catalyzed intramolecular cyclocarbonylation or intermolecular carboalkoxylation, respectively, of hydroxyl-containing 3-iodofurans, readily prepared by the iodocyclization of 2-(1-alkynyl)-2-alken-1-ones in the presence of various diols.

| S-EPMC3096464 | biostudies-literature

Regioselective, one-pot, multi-component, green synthesis of substituted benzo[<i>c</i>]pyrazolo[2,7]naphthyridines.

Project description:An efficient and environmentally benign synthetic protocol has been developed for the synthesis of benzo[c]pyrazolo[2,7]naphthyridine derivatives through regioselective multi-component "on-water" reaction of isatin, malononitrile and 3-aminopyrazole. The Knoevenagel condensation of isatin with malononitrile resulted in the formation of arylidene, which subsequently underwent Michael addition with 3-aminopyrazole followed by basic hydrolysis, cyclization, decarboxylation and aromatization to give the target naphthyridines in good to excellent yields. The one-pot multi-component protocol was also employed to obtain the said naphthyridines in a lower yield (10-15%) than obtained by basic hydrolysis of spiro-intermediates. The present study shows attractive features such as the use of water as a green solvent, short reaction time, reduced waste products and transition metal free C-C and C-N bond formation. The structures of the synthesized derivatives were established through FTIR, 1H-NMR, 13C-NMR spectroscopy and ESI-mass spectrometry.

| S-EPMC9049208 | biostudies-literature

Library-to-Library Synthesis of Highly Substituted ?-Aminomethyl Tetrazoles via Ugi Reaction.

Project description:?-Aminomethyl tetrazoles, recently made accessible by an Ugi multicomponent reaction (MCR), were shown to be excellent starting materials for a further Ugi MCR, yielding substituted N-methyl-2-(((1-methyl-1H-tetrazol-5-yl)methyl)amino)acetamides having four points of diversity in a library-to-library approach. The scope and limitations of the two-step sequence was explored by conducting more than 50 reactions. Irrespective of electron-rich and electron-deficient oxo-components and the nature of the isocyanide component, the reactions give excellent yields. Sterically less hindered ?-aminomethyl tetrazoles give better yields of in further Ugi MCR. The target scaffold has four points of diversity and is finding applications to fill screening decks for high-throughput screening (HTS) in the European Lead Factory and in structure-based drug design.

| S-EPMC5813278 | biostudies-literature

Design, synthesis, and diversification of 3,5-substituted enone library.

Project description:This paper describes the synthesis of a 300 member library of 3,5-substituted enones. The synthesis starts with 6 different bromoenones that are accessed from the corresponding 1,3 diones. These bromides are then diversified by Suzuki coupling with a variety of aromatic and vinyl boronic acids. Additionally a small series of triazoles was synthesized by a Sonogashira coupling reaction dipolar cycloaddition sequence. The library was analyzed by principal component analysis to examine its diversity.

| S-EPMC3360050 | biostudies-literature

Parallel synthesis of an oligomeric imidazole-4,5-dicarboxamide library.

Project description:A library of oligomeric compounds was synthesized based on the imidazole-4,5-dicarboxylic acid scaffold along with amino acid esters and chiral diamines derived from amino acids. The final compounds incorporate nonpolar amino acids (Leu, Phe, Trp), polar amino acids (Ser, Asp, Arg), and neutral amino acids (Gly, Ala), and were designed to be useful in screening for inhibitors of protein-protein interactions. Many of the protected and deprotected oligomers show evidence of conformational isomers persistent at room temperature in aqueous solution. A total of 317 final oligomers, out of 441 targeted compounds, were obtained in high analytical purity and of sufficient quantity to submit them for high-throughput screening as part of the NIH Roadmap.

| S-EPMC2846700 | biostudies-literature

Synthesis and κ-opioid receptor activity of furan-substituted salvinorin A analogues.

Project description:The neoclerodane diterpene salvinorin A, found in the leaves of Salvia divinorum, is a potent κ-opioid receptor agonist, making it an attractive scaffold for development into a treatment for substance abuse. Although several successful semisynthetic studies have been performed to elucidate structure-activity relationships, the lack of analogues with substitutions to the furan ring of salvinorin A has prevented a thorough understanding of its role in binding to the κ-opioid receptor. Herein we report the synthesis of several salvinorin A derivatives with modified furan rings. Evaluation of these compounds in a functional assay indicated that sterically less demanding substitutions are preferred, suggesting the furan ring is bound in a congested portion of the binding pocket. The most potent of the analogues successfully reduced drug-seeking behavior in an animal model of drug-relapse without producing the sedation observed with other κ-opioid agonists.

| S-EPMC4281103 | biostudies-literature

A Novel Base-Promoted Cyclization: Synthesis of Substituted Benzo[b]furans.

Project description:A new base-promoted cyclization for the synthesis of substituted benzo[b]furans is described. This method is simple and inexpensive and gives good yields.

| S-EPMC3529139 | biostudies-literature

Solution-phase parallel synthesis of a multisubstituted cyclic imidate library.

Project description:The solution-phase parallel synthesis of a diverse 71-member library of multisubstituted cyclic imidates is described. The key intermediates, 3-iodomethylene-containing cyclic imidates, are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodobenzamides and terminal alkynes, followed by electrophilic cyclization with I2. These cyclic imidates were further functionalized by palladium-catalyzed Suzuki-Miyaura, Sonogashira, carbonylative amidation, and Heck chemistry using sublibraries of commercially available building blocks.

| S-EPMC3740045 | 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