Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Rhodium-Catalyzed Merging of 2-Arylquinazolinone and 2,2-Difluorovinyl Tosylate: Diverse Synthesis of Monofluoroolefin Quinazolinone Derivatives.

ABSTRACT: An efficient method for the synthesis of 2-(o-monofluoroalkenylaryl)quinazolinone derivatives was developed. In this context, the quinazolinone ring served as the inherent directing group, 2,2-difluorovinyl tosylate was used as the monofluoroolefin synthon, and Rh(III)-catalyzed C-H bond difluorovinylation of 2-arylquinazolinons was performed to give the corresponding monofluoroalkene-containing quinazolinons in yields of 65-92%. The method is characterized by broad synthetic utility, mild conditions, and high efficiency.

SUBMITTER: Wang N

PROVIDER: S-EPMC7315571 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Rhodium-Catalyzed Merging of 2-Arylquinazolinone and 2,2-Difluorovinyl Tosylate: Diverse Synthesis of Monofluoroolefin Quinazolinone Derivatives.

Wang Ning N Yang Qin Q Deng Zhihong Z Mao Xuechun X Peng Yiyuan Y

ACS omega 20200615 24

An efficient method for the synthesis of 2-(<i>o</i>-monofluoroalkenylaryl)quinazolinone derivatives was developed. In this context, the quinazolinone ring served as the inherent directing group, 2,2-difluorovinyl tosylate was used as the monofluoroolefin synthon, and Rh(III)-catalyzed C-H bond difluorovinylation of 2-arylquinazolinons was performed to give the corresponding monofluoroalkene-containing quinazolinons in yields of 65-92%. The method is characterized by broad synthetic utility, mil ...[more]

PMID: 32596601

Similar Datasets

Multifaceted strategy for the synthesis of diverse 2,2'-bithiophene derivatives.

Project description:New catalytically or high pressure activated reactions and routes, including coupling, double bond migration in allylic systems, and various types of cycloaddition and dihydroamination have been used for the synthesis of novel bithiophene derivatives. Thanks to the abovementioned reactions and routes combined with non-catalytic ones, new acetylene, butadiyne, isoxazole, 1,2,3-triazole, pyrrole, benzene, and fluoranthene derivatives with one, two or six bithiophenyl moieties have been obtained. Basic sources of crucial substrates which include bithiophene motif for catalytic reactions were 2,2'-bithiophene, gaseous acetylene and 1,3-butadiyne.

| S-EPMC6272589 | biostudies-literature

Rhodium-catalyzed asymmetric hydroboration of ?,?-unsaturated amide derivatives: ?-borylated amides.

Project description:?,?-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed ?-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the ?-borylation of ?,?-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal in the sense of ?-facial selectivity.

| S-EPMC5975375 | biostudies-literature

2,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions.

Project description:gem-Difluoroalkene is a bioisostere of carbonyl group for improving bioavailability of drug candidates. Herein we develop structurally diverse 2,2-difluorovinyl benzoates (BzO-DFs) as versatile building blocks for modular synthesis of gem-difluoroenol ethers (44 examples) and gem-difluoroalkenes (2 examples) by Ni-catalyzed cross coupling reactions. Diverse BzO-DFs derivatives bearing sensitive functional groups (e.g., C = C, TMS, strained carbocycles) are readily prepared from their bromodifluoroacetates and bromodifluoroketones precursors using metallic zinc as reductant. With Ni(COD)2 and dppf [1,1'-bis(diphenylphosphino)ferrocene] as catalyst, reactions of BzO-DFs with arylboronic acids and arylmagnesium/alkylzinc reagents afforded the desired gem-difluoroenol ethers and gem-difluoroalkenes in good yields. The Ni-catalyzed coupling reactions features highly regioselective C(vinyl)-O(benzoate) bond activation of the BzO-DFs. Results from control experiments and DFT calculations are consistent with a mechanism involving initial oxidative addition of the BzO-DFs by the Ni(0) complex. By virtue of diversity of the BzO-DFs and excellent functional group tolerance, this method is amenable to late-stage functionalization of multifunctionalized bioactive molecules.

| S-EPMC7814061 | biostudies-literature

Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes.

Project description:The cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate (2) with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3 afforded the mono-coupled products 3 and 5 in high yields. The use of 4 equiv of boronic acids in the presence of catalytic amount of Pd(PPh3)2Cl2 and Na2CO3 in this reaction resulted in the formation of symmetrical di-coupled products 4 in high yields. Unsymmetrical di-coupled products 4 were obtained in high yields from the reactions of 3 with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3.

| S-EPMC3869221 | biostudies-literature

Asymmetric synthesis of ?-branched amines via rhodium-catalyzed reductive amination.

Project description:Amines bearing ?-stereocenters are highly important structural motifs in many biologically active compounds. However, reported enantioselective syntheses of these molecules are indirect and often require multiple steps. Herein, we report a general asymmetric route for the one-pot synthesis of chiral ?-branched amines through the highly enantioselective isomerization of allylamines, followed by enamine exchange and subsequent chemoselective reduction. This protocol is suitable for establishing various tertiary stereocenters, including those containing dialkyl, diaryl, cyclic, trifluoromethyl, difluoromethyl, and silyl substituents, which allows for a rapid and modular synthesis of many chiral ?-branched amines. To demonstrate the synthetic utility, Terikalant and Tolterodine are synthesized using this method with high levels of enantioselectivity.

| S-EPMC5864842 | biostudies-other

Expedient synthesis of fused azepine derivatives using a sequential rhodium(II)-catalyzed cyclopropanation/1-aza-Cope rearrangement of dienyltriazoles.

Project description:A general method for the formation of fused dihydroazepine derivatives from 1-sulfonyl-1,2,3-triazoles bearing a tethered diene is reported. The process involves an intramolecular cyclopropanation of an ?-imino rhodium(II) carbenoid, leading to a transient 1-imino-2-vinylcyclopropane intermediate which rapidly undergoes a 1-aza-Cope rearrangement to generate fused dihydroazepine derivatives in moderate to excellent yields. The reaction proceeds with similar efficiency on gram scale. The use of catalyst-free conditions leads to the formation of a novel [4.4.0] bicyclic heterocycle.

| S-EPMC4266427 | biostudies-literature

Synthesis of 1,3-diamines through rhodium-catalyzed C-H insertion.

Project description:A grand opening: N-Boc-N-alkylsulfamides are effective substrates for the title transformation. Oxidative cyclization is highly chemoselective as well as being both stereospecific and diastereoselective. With the advent of new protocols that facilitate ring opening of the six-membered-ring heterocyclic products, access to differentially protected 1,3-diamines has been made possible (see scheme).

| S-EPMC2822642 | biostudies-literature

Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic silicon-bridged arylpyridinones.

Project description:A rhodium-catalyzed regio- and enantioselective synthesis of silicon-stereogenic silicon-bridged arylpyridinones has been developed through [2 + 2 + 2] cycloaddition of silicon-containing prochiral triynes with isocyanates. High yields and enantioselectivities have been achieved by employing an axially chiral monophosphine ligand, and this process could be applied to catalytic asymmetric synthesis of silicon-stereogenic chiral polymers for the first time. The reaction mechanism of the present catalysis has also been experimentally investigated to establish a reasonable catalytic cycle, advancing the mechanistic understanding of the rhodium-catalyzed pyridinone synthesis by [2 + 2 + 2] cycloaddition reactions.

| S-EPMC5975726 | biostudies-literature

Synthesis, antimicrobial evaluation and docking studies of some novel quinazolinone Schiff base derivatives.

Project description:The quinazolin-4(3H)-one structural motif possesses a wide spectrum of biological activities. DNA gyrase play an important role in induction of bacterial death. It has been shown that many quinazolin-4(3H)-one derivatives have antibacterial effects through inhibition of DNA gyrase. Based on this information we decided to synthesize novel quinazolinone Schiff base derivatives in order to evaluate their antibacterial effects. A series of novel quinazolinone Schiff base derivatives were designed and synthesized from benzoic acid. The potential DNA gyrase inhibitory activity of these compounds was investigated using in silico molecular docking simulation. All new synthesized derivatives were screened for their antimicrobial activities against three species of Gram-negative bacteria including Escherichia coli, Pseudomonas aeruginosa, Salmonella entritidis and three species of Gram-positive bacteria comprising of Staphylococcus aurous, Bacillus subtilis, Listeria monocitogenes as well as for antifungal activities against Candida albicans using the conventional micro dilution method. Most of the compounds have shown good antibacterial activities, especially against E. coli at 128 µg/mL concentration while no remarkable antifungal activities were observed for these compounds. All the synthesized compounds exhibit dock score values between -5.96 and -8.58 kcal/mol. The highest dock score among them was -8.58 kcal/mol for compound 4c.

| S-EPMC5921402 | biostudies-literature

Facile One-Pot Synthesis of Functionalized Quinoline-Fused Fluorescent Dihydro/Spiro-quinazolinone Derivatives.

Project description:A facile and efficient method has been developed for the synthesis of quinoline-fused fluorescent dihydro/spiro-quinazolinones. A plausible mechanism involving an acid-mediated enaminone intermediate is provided. The reaction proceeded using p-toluene sulfonic acid as a green promoter. The methodology was successful in synthesizing various quinoline-appended spiro-quinazolinones 4a-o. The synthetic utility of compounds 4a-o was demonstrated by synthesizing compounds 6a-d via Suzuki coupling as a key reaction. Significantly, the π-π* electronic transition of compounds 4c and 4k showed a blue shift. The molar extinction coefficient (ε), Stoke's shift (Δu̅), and quantum yield (Φf)c were calculated for these derivatives (4c and 4k).

| S-EPMC9219092 | 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