Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Asymmetric synthesis of 2,4,5-trisubstituted ?2-thiazolines.

ABSTRACT: ?(2)-Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5-trisubstituted ?(2)-thiazolines. These ?(2)-thiazolines were synthesized from readily accessible/commercially available ?,?-unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O?N acyl migration reaction as key steps. The final products were obtained in good yields with up to 97?% enantiomeric excess.

SUBMITTER: Bengtsson C

PROVIDER: S-EPMC3784040 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Asymmetric synthesis of 2,4,5-trisubstituted Δ2-thiazolines.

Bengtsson Christoffer C Nelander Hanna H Almqvist Fredrik F

Chemistry (Weinheim an der Bergstrasse, Germany) 20130617 30

Δ(2)-Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5-trisubstituted Δ(2)-thiazolines. These Δ(2)-thiazolines were synthesized from readily accessible/commercially available α,β-unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O→N acyl migration reaction as key steps. Th ...[more]

PMID: 23776083

Similar Datasets

2,4,5-Trisubstituted Pyrimidines as Potent HIV-1 NNRTIs: Rational Design, Synthesis, Activity Evaluation, and Crystallographic Studies.

Project description:There is an urgent unmet medical need for novel human immunodeficiency virus type 1 (HIV-1) inhibitors that are effective against a variety of NNRTI-resistance mutations. We report our research efforts aimed at discovering a novel chemotype of anti-HIV-1 agents with improved potency against a variety of NNRTI-resistance mutations in this paper. Structural modifications of the lead K-5a2 led to the identification of a potent inhibitor 16c. 16c yielded highly potent anti-HIV-1 activities and improved resistance profiles compared with the approved drug etravirine. The co-crystal structure revealed the key role of the water networks surrounding the NNIBP for binding and for resilience against resistance mutations, while suggesting further extension of 16c toward the NNRTI-adjacent site as a lead development strategy. Furthermore, 16c demonstrated favorable pharmacokinetic and safety properties, suggesting the potential of 16c as a promising anti-HIV-1 drug candidate.

| S-EPMC8594587 | biostudies-literature

m-Chloroperbenzoic acid-oxchromium (VI)-mediated cleavage of 2,4,5-trisubstituted oxazoles.

Project description:An array of 2-substituted-4,5-diphenyloxazoles were found to be cleaved to triacylamines and diacylamines (imides) using a reagent system composed of 3-chloroperbenzoic acid (MCPBA) and 2,2'-bipyridinium chlorochromate (BPCC). The 2-alkyl-4,5-diphenyloxazoles give imides (38-60%) as the predominant cleavage product while the 2-aryl-4,5-diphenyloxazoles give triacylamines (44-71%). Two mechanisms involving intermediates such as cyclic endoperoxides or oxachromacycles were proposed. An application of the oxidative cleavage to the multi-step synthesis of (±)-phoracantholide I seco acid is detailed.

| S-EPMC5621761 | biostudies-literature

Gold-catalyzed tandem reactions of amide-aldehyde-alkyne coupling and cyclization-synthesis of 2,4,5-trisubstituted oxazoles.

Project description:We report the first cationic gold(i)-catalyzed one-pot reaction of amide, alkyne and aldehyde followed by cyclization, to successfully access highly substituted oxazoles derivatives in good yields. A single catalyst allows the occurring of this multi-step reaction atom- and step-economically, with water as the only theoretical side product.

| S-EPMC5950834 | biostudies-other

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid.

Project description:A novel method for the synthesis of trisubstituted oxazoles via a one-pot oxazole synthesis/Suzuki-Miyaura coupling sequence has been developed. One-pot formation of 5-(triazinyloxy)oxazoles using carboxylic acids, amino acids and a dehydrative condensing reagent, DMT-MM, followed by Ni-catalyzed Suzuki-Miyaura coupling with boronic acids provided the corresponding 2,4,5-trisubstituted oxazoles in good yields.

| S-EPMC5550800 | biostudies-literature

Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes.

Project description:Highly enantioselective rhodium-catalyzed hydroboration of allylic phosphonates by pinacolborane affords chiral tertiary boronic esters. The β-borylated phosphonates are readily converted to chiral β- and γ-hydroxyphosphonates and aminophosphonates and to phosphonates bearing a quaternary carbon stereocenter. The utility of the latter is illustrated by the synthesis of (S)-(+)-bakuchiol methyl ether.

| S-EPMC5423446 | biostudies-literature

An efficient multicomponent synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetic nanoparticle supported Lewis acidic deep eutectic solvent.

Project description:A mild and highly efficient reaction for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetically supported Lewis acidic deep eutectic solvent on magnetic nanoparticles (LADES@MNP) has been developed via one-pot multicomponent processes under solvent-free sonication. These reactions have good to excellent yields, mild conditions, and work-up simplicity. This method represents a new method for the preparation of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles. More importantly, LADES@MNP can be easily recovered by magnetic separation and reused five times without significant loss of catalytic activity.

| S-EPMC9075852 | biostudies-literature

Exploring the untapped catalytic application of a ZnO/CuI/PPy nanocomposite for the green synthesis of biologically active 2,4,5-trisubstituted imidazole scaffolds.

Project description:This work is focused on designing an innovative, efficient, and reusable heterogeneous ZnO/CuI/PPy nanocomposite via the self-assembly approach where pyrrole is oxidized into polypyrrole (PPy) and pyrrole also behaves as a reductant in the presence of KI. This so-obtained material was characterized by XRD, FTIR, FESEM, EDX, TEM, XPS, and ICP. TEM clearly shows a spherical morphology with the particle size ranging between 18 and 42 nm. The fabricated nanomaterial was tested for one-pot catalytic synthesis of biologically active 2,4,5-trisubstituted imidazoles under solvent-free conditions. The present work includes the benefits of an easy work-up procedure, higher product yield, shorter reaction duration, and no additional additive requirement under green and sustainable conditions. Moreover, the catalyst exhibited reusability for six runs with no considerable reduction in the respective yields and reactivity (confirmed by XRD, SEM, and TEM of the recycled catalyst). The ICP study shows very low leaching of copper (2.08 ppm) and zinc (0.12 ppm) metals. The approach also presented better values of green metrics like the E-factor, process mass intensity, carbon efficiency and reaction mass efficiency.

| S-EPMC10089100 | biostudies-literature

Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes.

Project description:Rhodium-catalyzed hydroborations of trisubstituted alkenes are generally slow and often suffer from competing alkene isomerization. In contrast, the trisubstituted alkene moieties contained within the framework of a beta,gamma-unsaturated amide undergo facile reaction, perhaps facilitated by carbonyl directing effects and two-point binding of the substrate to the rhodium catalyst. Stereoisomeric substrates, for example, (E)- and (Z)-3, cleanly give rise to diastereomeric products, and thus the rhodium-catalyzed reaction is stereospecific. In addition, simple TADDOL-derived phenyl monophosphite ligands in combination with Rh(nbd)(2)BF(4) afford highly enantioselective catalysts (seven examples, 91-98% ee). These catalysts provide an alternative methodology to prepare Felkin or anti-Felkin acetate-aldol products and related derivatives that are obtainable from the intermediate chiral organoboranes.

| S-EPMC2846594 | biostudies-literature

Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole Analogues.

Project description:A series of 2,4,5 trisubstituted-1,2,3-triazole analogues have been screened for their antifungal activity against five fungal strains, Candida parapsilosis, Candida albicans, Candida tropicalis, Aspergillus niger, and Trichophyton rubrum, via a 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) microdilution assay. Compounds GKV10, GKV11, and GKV15 emerged as promising antifungal agents against all the fungal strains used in the current study. One of the highly active antifungal compounds, GKV10, was selected for a single-crystal X-ray diffraction analysis to unequivocally establish its molecular structure, conformation, and to understand the presence of different intermolecular interactions in its crystal lattice. A cooperative synergy of the C-H···O, C-H···N, C-H···S, C-H···π, and π···π intermolecular interactions was present in the crystal structure, which contributed towards the overall stabilization of the lattice. A molecular docking study was conducted for all the test compounds against Candida albicans lanosterol-14α-demethylase (pdb = 5 tzl). The binding stability of the highly promising antifungal test compound, GKV15, from the series was then evaluated by molecular dynamics studies.

| S-EPMC7344790 | biostudies-literature

Iron(II)-Catalyzed Asymmetric Epoxidation of Trisubstituted ?,?-Unsaturated Esters.

Project description:An asymmetric epoxidation of trisubstituted ?,?-unsaturated esters is described. The oxidation utilizes a pseudo-C2-symmetric iron(II) catalyst [Fe(L*)2(CH3CN)(OTf)](OTf) and peracetic acid as oxidant, yielding the ?,?-epoxyesters in high enantiomeric purity (up to 99% ee).

| S-EPMC4486291 | 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