Browse
Submit Data
Databases
API
Help

Dataset Information

26 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Exploiting the Nucleophilicity of the Nitrogen Atom of Imidazoles: One-Pot Three-Component Synthesis of Imidazo-Pyrazines.

ABSTRACT: A novel one-pot multicomponent reaction to synthesize substituted imidazopyrazines is described. In brief, 1H-(imidazol-5-yl)-N-substituted methanamines react with aldehydes and isocyanides in methanol at room temperature to give imidazopyrazine derivatives in excellent yields. The imidazole nitrogen atom was able to intercept the nascent nitrilium ion, channeling the reaction toward to the sole formation of imidazopyrazines, suppressing the competitive formation of other possible side products deriving from the reaction with the high-energy nitrilium ion. The number of examples and the variability of the nature of isocyanides, aldehydes, and amine components herein employed, witness the robustness of this novel methodology.

SUBMITTER: Galli U

PROVIDER: S-EPMC6572241 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Exploiting the Nucleophilicity of the Nitrogen Atom of Imidazoles: One-Pot Three-Component Synthesis of Imidazo-Pyrazines.

Galli Ubaldina U Hysenlika Rejdia R Meneghetti Fiorella F Del Grosso Erika E Pelliccia Sveva S Novellino Ettore E Giustiniano Mariateresa M Tron Gian Cesare GC

Molecules (Basel, Switzerland) 20190521 10

A novel one-pot multicomponent reaction to synthesize substituted imidazopyrazines is described. In brief, 1<i>H</i>-(imidazol-5-yl)-<i>N</i>-substituted methanamines react with aldehydes and isocyanides in methanol at room temperature to give imidazopyrazine derivatives in excellent yields. The imidazole nitrogen atom was able to intercept the nascent nitrilium ion, channeling the reaction toward to the sole formation of imidazopyrazines, suppressing the competitive formation of other possible ...[more]

PMID: 31117306

Similar Datasets

One-pot synthesis of tetracyclic fused imidazo[1,2-a]pyridines via a three-component reaction.

Project description:A novel three-component reaction has been developed to assemble biologically and pharmaceutically important tetracyclic fused imidazo[1,2-a]pyridines in a one-pot fashion utilizing readily available 2-aminopyridines, isatins and isocyanides. The three-component coupling proceeds through the Groebke-Blackburn-Bienaymé reaction followed by a retro-aza-ene reaction and subsequent nucleophilic reaction of the in-situ generated imidazo[1,2-a]pyridines bearing an isocyanate functional group.

| S-EPMC4979633 | biostudies-literature

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-pot, three-component arylalkynyl sulfone synthesis.

Project description:A one-pot three-component protocol for the preparation of arylsulfonyl alkynes through the reaction of ethynyl-benziodoxolone (EBX) reagents, DABSO (DABCO·SO2), and either organomagnesium reagents or aryl iodides with a palladium catalyst is reported. A broad range of aryl and heteroarylalkynyl sulfones were obtained in 46-85% overall yield.

| S-EPMC4342956 | biostudies-literature

Catalyst-Free One-Pot Synthesis of Densely Substituted Pyrazole-Pyrazines as Anti-Colorectal Cancer Agents.

Project description:The first catalyst-free post-Ugi cascade methodology was developed for expeditious access to structurally diverse and complex pyrazole-pyrazines in one-pot. This novel cascade reaction features an intramolecular N2-arylation of pyrazoles with allenes at the C-β position of triple bond. Screening in the colorectal cancer cell lines HCT116 and SW620 validated the feasibility of the methodology for generating bioactive compounds. The lead compound 7h which is active against HCT116 and SW620 with IC50 of 1.3 and 1.8 µM, respectively, can be synthesized and purified in a gram process synthetic scale in 7 hours. The mechanical studies indicated that compound 7h can induce cell cycle arrest in the G2/M phase and inhibit proliferation and viability in human colon cancer cells. Overall, compound 7h is represented as a promising starting point for the development of new anti-colorectal cancer drugs.

| S-EPMC7283261 | biostudies-literature

DABSO-based, three-component, one-pot sulfone synthesis.

Project description:The addition of Grignard reagents or organolithium reagents to the SO2-surrogate DABSO generates a diverse set of metal sulfinates, suitable for direct conversion to sulfone products. The metal sulfinates can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums.

| S-EPMC3883144 | biostudies-literature

Re-designing nano-silver technology exploiting one-pot hydroxyethyl cellulose-driven green synthesis.

Project description:Re-designing existing nano-silver technologies to optimize efficacy and sustainability has a tangible impact on preventing infections and limiting the spread of pathogenic microorganisms. Advancements in manufacturing processes could lead to more cost-effective and scalable production methods, making nano-silver-based antimicrobial products more accessible in various applications, such as medical devices, textiles, and water purification systems. In this paper, we present a new, versatile, and eco-friendly one-pot process for preparing silver nanoparticles (AgNPs) at room temperature by using a quaternary ammonium salt of hydroxyethyl cellulose (HEC), a green ingredient, acting as a capping and reducing agent. The resulting nano-hybrid phase, AgHEC, consists of AgNPs embedded into a hydrogel matrix with a tunable viscosity depending on the conversion grade, from ions to nanoparticles, and on the pH. To investigate the synthesis kinetics, we monitored the reaction progress within the first 24 h by analyzing the obtained NPs in terms of particle size (dynamic light scattering (DLS), field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM)), Z-potential (ELS), surface plasmon resonance (UV-VIS), crystallographic phase (XRD), viscosity, and reaction yield (inductively coupled plasma-optical emission spectrometry (ICP-OES)). To explore the design space associated with AgHEC synthesis, we prepared a set of sample variants by changing two independent key parameters that affect nucleation and growth steps, thereby impacting the physicochemical properties and the investigated antimicrobial activity. One of the identified design alternatives pointed out an improved antimicrobial activity in the suspension, which was confirmed after application as a coating on nonwoven cellulose fabrics. This enhancement was attributed to a lower particle size distribution and a positive synergistic effect with the HEC matrix.

| S-EPMC11349673 | biostudies-literature

Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach.

Project description:5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke-Blackburn-Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe an operationally simple, one-pot two-step GBB protocol for the rapid construction of a 46 membered imidazo[1,2-b]pyrazole library with yields up to 83%.

| S-EPMC4222397 | biostudies-literature

Diastereoselective One Pot Five-Component Reaction toward 4-(Tetrazole)-1,3-Oxazinanes.

Project description:A diastereoselective one pot five-component reaction toward the synthesis of 4-(tetrazole)-1,3-oxazinanes has been reported. The sonication-accelerated, catalyst-free, simple, general and highly time efficient, Asinger-Ugi-tetrazole reaction was used for the synthesis of diverse 4-(tetrazole)-1,3-oxazinanes. The reaction exhibit excellent diastereoselectivity and broad substrate scope.

| S-EPMC5802416 | biostudies-literature

Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles.

Project description:The pyrazole scaffold is one of the most prevalent and important tool in medicinal chemistry. Here, we report a method for preparing 3,5-diarylpyrazoles in good to excellent yield by reacting hydrazones of aryl aldehydes with substituted acetophenones in ethanol in the presence of dimethyl sulfoxide/cat. I2/cat. HCl. The reverse process, reacting hydrazones of substituted acetophenones with aryl aldehydes under the same conditions, also provides 3,5-diarylpyrazoles in good to excellent yields. Reaction of hydrazones of aldehydes with 2'-aryloxy ketones in the presence of cat. HCl in ethanol and the catalyst-free reaction of phenacyl bromides with hydrazones of aldehydes in ethanol also gave good to excellent yields of 3,5-diarylpyrazoles.

| S-EPMC6643981 | biostudies-literature

Three-Component One-Pot Synthesis of Highly Functionalized Bis-Indole Derivatives.

Project description:In this study, we detail the development of a concise and efficient three-component protocol for the regioselective synthesis of highly functionalized bis-indoles through a one-pot, two-step sequential process starting from enaminones 1, indoles 2, and acenaphthylene-1,2-dione 3 that is catalyzed by piperidine and p-methyl benzenesulfonic acid. This protocol has several advantages including simplicity of experimental operation, high efficiency of bond formation, ready availability and low cost of starting materials, environmentally benign conditions, and target molecular diversity.

| S-EPMC6682060 | 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