Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of benzisoxazolines by the coupling of arynes with nitrones.

ABSTRACT: A variety of substituted benzisoxazolines have been synthesized by the [3 + 2] cycloaddition of nitrones and arynes. The reaction scope is broad, the reaction conditions are mild, and the process tolerates a variety of functional groups.

SUBMITTER: Lu C

PROVIDER: S-EPMC3293248 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of benzisoxazolines by the coupling of arynes with nitrones.

Lu Chun C Dubrovskiy Anton V AV Larock Richard C RC

The Journal of organic chemistry 20120216 5

A variety of substituted benzisoxazolines have been synthesized by the [3 + 2] cycloaddition of nitrones and arynes. The reaction scope is broad, the reaction conditions are mild, and the process tolerates a variety of functional groups. ...[more]

PMID: 22329405

Similar Datasets

Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates.

Project description:The reaction of silylaryl triflates, CsF, and ortho-heteroatom-substituted benzoates affords a general and efficient way to prepare biologically interesting xanthones, thioxanthones, and acridones. This chemistry presumably proceeds by a tandem intermolecular nucleophilic coupling of the benzoate with an aryne and a subsequent intramolecular electrophilic cyclization.

| S-EPMC2529457 | biostudies-literature

Synthesis of Phenolic Compounds by Trapping Arynes with a Hydroxy Surrogate.

Project description:Trapping of arynes with various nucleophiles provides a range of heteroatom-functionalized arene derivatives, but the corresponding reaction with water does not provide phenol derivatives. Silver trifluroacetate (AgO?CCF?) can nicely solve this problem. It was found that in typical organic solvent, AgO?CCF? readily reacts with arynes to generate trifluoroacetoxy organosilver arene intermediate, which, upon treating with silica gel, provides phenolic products. This protocol can be extended to the synthesis of ?-halofunctionalized phenol derivatives by simply adding NBS (N-bromosuccinimides) or NIS (N-iodosuccinimides) to the reaction along with silver trifluroacetate, which provided ?-bromo or ?-iodophenol derivatives in good yield. However, the similar reactions with NCS (N-chlorosuccinimides) afforded only the protonated product instead of the expected ?-chlorophenols derivatives. Interestingly, substrates containing silyl substituents on 1,3-diynes resulted in ?-halotrifluoroacetates rather than their hydrolyzed product. Additionally, trapping the same arynes with other oxygen-based nucleophiles containing silver counter cation, along with NXS (N-halosuccinimides), generated ?-halooxyfunctionalized products.

| S-EPMC6331853 | biostudies-other

Intrinsic Coupling of Lagging Strand Synthesis to Chromatin Assembly

Project description:We show that ligation-competent Okazaki fragments in Saccharomyces cerevisiae are sized according to the chromatin repeat. Using deep sequencing, we demonstrate that ligation junctions preferentially occur around nucleosome midpoints rather than in internucleosomal linker regions. Disrupting chromatin assembly or lagging strand polymerase processivity impacts both the size and the distribution of Okazaki fragments, suggesting a role for nascent chromatin, assembled immediately after the passage of the replication fork, in the termination of lagging strand synthesis. Our studies represent the first high-resolution analysis of eukaryotic Okazaki fragments in vivo, and establish a mechanistic link between the fundamental processes of DNA replication and chromatin assembly. 4 samples: replicate samples of wild-type and pol32 knockout

2012-02-21 | E-GEOD-33786 | biostudies-arrayexpress

Palladium-catalyzed annulation of arynes by o-halobenzamides: synthesis of phenanthridinones.

Project description:The palladium-catalyzed annulation of arynes by substituted o-halobenzamides produces N-substituted phenanthridinones in good yields. This methodology provides this important heterocyclic ring system in a single step by simultaneous C-C and C-N bond formation, under relatively mild reaction conditions, and tolerates a variety of functional groups.

| S-EPMC3490708 | biostudies-literature

Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines.

Project description:Dihydrobenzisoxazoles are readily prepared in good yields by the [3 + 2] cycloaddition of oxaziridines and arynes. The reaction involves an unusual cleavage of the C-O bond of the oxaziridine and tolerates a variety of substituents on the oxaziridine and the o-(trimethylsilyl)aryl triflate to form aryl-, heteroaryl-, alkyl-, and naphthyl-substituted dihydrobenzisoxazoles. The resulting halogen-substituted dihydrobenzisoxazoles are readily elaborated to more complex products using palladium-catalyzed crossing-coupling processes.

| S-EPMC2975568 | biostudies-literature

An efficient synthesis of aldohexose-derived piperidine nitrones: precursors of piperidine iminosugars.

Project description:D-glucopyranose-derived and L-idopyranose-derived piperidine nitrones were synthesized in good overall yields through six-step reaction sequence starting from readily available 2,3,4,6-tetra-O-benzyl-D-glucopyranose. The method is efficient and could be general for the synthesis of aldohexose-derived piperidine nitrones which are precursors of piperidine iminosugars.

| S-EPMC6270483 | biostudies-literature

Synthesis and Neuroprotective Properties of N-Substituted <i>C</i>-Dialkoxyphosphorylated Nitrones.

Project description:Herein, we report the synthesis and neuroprotective power of some N-substituted C-(dialkoxy)phosphorylated nitrones 4a-g, by studying their ability to increase the cell viability, as well as their capacity to reduce necrosis and apoptosis. We have identified (Z)-N-tert-butyl-1-(diethoxyphosphoryl)methanimine oxide (4e) as the most potent, nontoxic, and neuroprotective agent, with a high activity against neuronal necrotic cell death, a result that correlates very well with its great capacity for the inhibition of the superoxide production (72%), as well as with the inhibition of lipid peroxidation (62%), and the 5-lipoxygenase activity (45%) at 100 μM concentrations. Thus, nitrone 4e could be a convenient promising compound for further investigation.

| S-EPMC6648307 | biostudies-literature

Synthesis of 9-Substituted Xanthenes by the Condensation of Arynes with ortho-Hydroxychalcones.

Project description:The reaction of o-(trimethylsilyl)aryl triflates, CsF, and o-hydroxychalcones affords a general and efficient way to prepare biologically interesting 9-substituted xanthenes. This chemistry presumably proceeds by tandem intermolecular nucleophilic attack of the phenoxide of the chalcone on the aryne and subsequent intramolecular Michael addition. The introduction of an external base, Cs(2)CO(3), has proven beneficial in this reaction.

| S-EPMC3314341 | biostudies-literature

Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones.

Project description:A rapid and efficient synthesis of 2H-indazoles has been developed, which involves the [3 + 2] dipolar cycloaddition of arynes and sydnones. The process proceeds under mild reaction conditions in good to excellent yields.

| S-EPMC2871071 | biostudies-literature

Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction.

Project description:A method for the one-step construction of 3,3,4,4-tetrafluorinated piperidines from nitrones and readily accessible tetrafluorinated iodobromobutane is described. The reaction requires an excess amount of ascorbic acid as the terminal reductant and is performed in the presence of an iridium photocatalyst activated by blue light. The annelation is a result of a radical addition at the nitrone, intramolecular nucleophilic substitution, and reduction of the N-O bond.

| S-EPMC7783028 | 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