Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

One-step synthesis of imidazoles from Asmic (anisylsulfanylmethyl isocyanide).

ABSTRACT: Substituted imidazoles are readily prepared by condensing the versatile isocyanide Asmic, anisylsulfanylmethylisocyanide, with nitrogenous π-electrophiles. Deprotonating Asmic with lithium hexamethyldisilazide effectively generates a potent nucleophile that efficiently intercepts nitrile and imine electrophiles to afford imidazoles. In situ cyclization to the imidazole is promoted by the conjugate acid, hexamethyldisilazane, which facilitates the requisite series of proton transfers. The rapid formation of imidazoles and the interchange of the anisylsulfanyl for hydrogen with Raney nickel make the method a valuable route to mono- and disubstituted imidazoles.

SUBMITTER: Mueller LG

PROVIDER: S-EPMC8239262 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

One-step synthesis of imidazoles from Asmic (anisylsulfanylmethyl isocyanide).

Mueller Louis G LG Chao Allen A AlWedi Embarek E Fleming Fraser F FF

Beilstein journal of organic chemistry 20210624

Substituted imidazoles are readily prepared by condensing the versatile isocyanide Asmic, anisylsulfanylmethylisocyanide, with nitrogenous π-electrophiles. Deprotonating Asmic with lithium hexamethyldisilazide effectively generates a potent nucleophile that efficiently intercepts nitrile and imine electrophiles to afford imidazoles. In situ cyclization to the imidazole is promoted by the conjugate acid, hexamethyldisilazane, which facilitates the requisite series of proton transfers. The rapid f ...[more]

PMID: 34239617

Similar Datasets

One-Pot NBS-Promoted Synthesis of Imidazoles and Thiazoles from Ethylarenes in Water.

Project description:A facile and eco-friendly method has been developed for the synthesis of imidazoles and thiazoles from ethylarenes in water. The reaction proceeds via in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant, followed by trapping with suitable nucleophiles to provide the corresponding products in good yields under metal-free conditions.

| S-EPMC6429224 | biostudies-literature

One-step synthesis of carbon-supported electrocatalysts.

Project description:Cost-efficiency, durability, and reliability of catalysts, as well as their operational lifetime, are the main challenges in chemical energy conversion. Here, we present a novel, one-step approach for the synthesis of Pt/C hybrid material by plasma-enhanced chemical vapor deposition (PE-CVD). The platinum loading, degree of oxidation, and the very narrow particle size distribution are precisely adjusted in the Pt/C hybrid material due to the simultaneous deposition of platinum and carbon during the process. The as-synthesized Pt/C hybrid materials are promising electrocatalysts for use in fuel cell applications as they show significantly improved electrochemical long-term stability compared to the industrial standard HiSPEC 4000. The PE-CVD process is furthermore expected to be extendable to the general deposition of metal-containing carbon materials from other commercially available metal acetylacetonate precursors.

| S-EPMC7509379 | biostudies-literature

A bioinspired, one-step total synthesis of peshawaraquinone.

Project description:A concise synthesis of a stereochemically complex meroterpenoid, peshawaraquinone, via the unsymmetrical dimerization of its achiral precursor, dehydro-α-lapachone, is reported. Enabled by reversible oxa-6π-electrocyclizations of 2H-pyran intermediates, the base-catalyzed dimerization sets up an intramolecular (3 + 2) cycloaddition, with the formation of six stereocenters during the cascade. Combining the generation and in situ dimerization of dehydro-α-lapachone allows a one-step total synthesis of peshawaraquinone from lawsone and prenal.

| S-EPMC9890946 | biostudies-literature

One-step synthesis of oxazoline and dihydrooxazine libraries.

Project description:The reactions of 1,2- and 1,3-hydroxyalkyl azides and aldehydes in the presence of Lewis acid result in the one-step construction of oxazolines and dihydrooxazines, respectively. The reaction was adapted to parallel synthesis using a polymer-bound phosphine to scavenge excess hydroxyalkyl azide. Thus, a 60-member library of various disubstituted oxazolines and di- and trisubstituted dihydrooxazines was generated.

| S-EPMC2539067 | biostudies-literature

One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines.

Project description:An operationally simple, one-pot, two-step cascade method has been developed to afford quinazolino[1,2,3]triazolo[1,4]benzodiazepines. This unique, atom-economical transformation engages five reactive centers (amide, aniline, carbonyl, azide, and alkyne) and employs environmentally benign iodine as a catalyst. The method proceeds via sequential quinazolinone-forming condensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions. Substrate scope, multicomponent examples, and mechanistic insights are discussed.

| S-EPMC3486955 | biostudies-literature

Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.

Project description:The synthesis of spiro[indoline-3,2'-pyrrole]-2,5'(1'H)-diones and spiro[indoline-3,2'-pyrrolidine]-2,5'-diones, via a post-Ugi-domino transamidation/cyclization sequential process, has been achieved in three sequential steps utilizing a one-pot reaction protocol. The variation in carboxylic acid substrates allows for the generation of new chiral racemic quaternary carbon centers under basic conditions providing molecular diversity and a small library of spirocyclic oxindoles.

| S-EPMC5942382 | biostudies-literature

A One-Pot Synthesis of Oxazepine-Quinazolinone bis-Heterocyclic Scaffolds via Isocyanide-Based Three-Component Reactions.

Project description:A novel, efficient and environmentally friendly approach has been developed for the synthesis of biologically important bis-heterocyclic oxazepine-quinazolinone derivatives. The structurally interesting compounds of high purity were synthesized by a one-pot three-component reaction of 2-(2-formylphenoxy) acetic acid and 2-aminobenzamide as bifunctional reagents and an isocyanide without using any catalyst, with excellent overall yields.

| S-EPMC6759581 | biostudies-literature

Asymmetrically Substituted s-Triazine Phosphonates by One-Step Synthesis.

Project description:Asymmetrically substituted s-triazine phosphonates with up to three different phosphonate groups C3 N3 RR'R" with R, R', R"=PO(OR"') and R"'=for example, methyl, ethyl, isopropyl or n-butyl are interesting as polymer additives like flame retardants. Typically, these compounds are obtained by multiple synthesis steps. However, this leads to high production costs, which are a disadvantage for commercial use. Here we report the one-step synthesis of mixtures of asymmetrical s-triazine phosphonates which is an easy way to adjust the thermal behaviour and other properties such as viscosities of the compounds. The synthesis is based on a Michaelis-Arbuzov reaction. A complete conversion of the reactants to the target compounds is observed which was proofed by detailed 1 H, 13 C and 31 P NMR investigations and elemental analysis. The thermal behaviour was compared with thermogravimetric analysis (TGA).

| S-EPMC10509391 | biostudies-literature

One-Step Hydrothermal Synthesis of Comb-Like ZnO Nanostructures.

Project description:Zinc Oxide (ZnO) nano-superstructures (NSSs) have attracted intense research interests due to their large surface areas and unique properties. In this work, we report an original approach to synthesize ZnO NSSs in a one-step manner with a hydrothermal method. The crystalline structures and growth mechanism can be understood by surface energy calculations. The reaction kinetics was investigated for the control of the morphology of ZnO NSSs. The critical role of the morphology of Au catalysts in the synthesis of ZnO nanostructures has been demonstrated. Such ZnO NSSs can be fabricated on various rigid and flexible substrates for applications in electronics, solar cells and piezoelectric devices.

| S-EPMC3500587 | biostudies-literature

One-step multicomponent synthesis of chiral oxazolinyl-zinc complexes.

Project description:BACKGROUND:Typically, oxazolinyl metal complexes are synthesized in two steps, where the free ligand is prepared by the condensation reaction between a functionalized nitrile and an amino alcohol in the presence of a Lewis or Brønsted acid catalyst, followed by a further reaction with metal salts to obtain the corresponding metal complexes. Very often, the yield afforded by the two-step procedure is not high, and very few oxazolinyl zinc complexes have been prepared by this route. Given that metal-oxazoline complexes often contain Lewis acidic metals, it is conceivable that the two steps may be telescoped. RESULTS:A series of novel chiral organozinc complexes 1-15 were assembled in a single step, All crystalline compounds were fully characterized, including the report of 15 X-ray crystal structures, including a wide structural diversity. CONCLUSIONS:A series of novel chiral organozinc complexes were assembled in a single step, from nitriles, chiral D/L amino alcohols, and a stoichiometric amount of ZnCl2, with moderate to high yields (20-90%).

| S-EPMC5549684 | 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