Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea.

ABSTRACT: The three-component reactions of aldehydes, electron deficient alkynes and ureas/thioureas have been smoothly performed to yield a class of unprecedented 3,4-dihydropyrimidinones and thiones (DHPMs). The reactions are initiated by the key transformation of an enamine-type activation involving the addition of a secondary amine to an alkyne, which enables the subsequent incorporation of aldehydes and ureas/thioureas. This protocol tolerates a broad range of aryl- or alkylaldehydes, N-substituted and unsubstituted ureas/thioureas and alkynes to yield the corresponding DHPMs with specific regioselectivity.

SUBMITTER: Wan JP

PROVIDER: S-EPMC3943560 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea.

Wan Jie-Ping JP Lin Yunfang Y Hu Kaikai K Liu Yunyun Y

Beilstein journal of organic chemistry 20140129

The three-component reactions of aldehydes, electron deficient alkynes and ureas/thioureas have been smoothly performed to yield a class of unprecedented 3,4-dihydropyrimidinones and thiones (DHPMs). The reactions are initiated by the key transformation of an enamine-type activation involving the addition of a secondary amine to an alkyne, which enables the subsequent incorporation of aldehydes and ureas/thioureas. This protocol tolerates a broad range of aryl- or alkylaldehydes, N-substituted a ...[more]

PMID: 24605149

Similar Datasets

Dihydropyrimidinones and -thiones with improved activity against human polyomavirus family members.

Project description:Human polyomaviruses are generally latent but can be reactivated in patients whose immune systems are suppressed. Unfortunately, current therapeutics for diseases associated with polyomaviruses are non-specific, have undefined mechanisms of action, or exacerbate the disease. We previously reported on a class of dihydropyrimidinones that specifically target a polyomavirus-encoded protein, T antigen, and/or inhibit a cellular chaperone, Hsp70, that is required for virus replication. To improve the antiviral activity of the existing class of compounds, we performed Biginelli and modified multi-component reactions to obtain new 3,4-dihydropyrimidin-2(1H)-ones and -thiones for biological evaluation. We also compared how substituents at the N-1 versus N-3 position in the pyrimidine affect activity. We discovered that AMT580-043, a N-3 alkylated dihydropyrimidin-2(1H)-thione, inhibits the replication of a disease-causing polyomavirus in cell culture more potently than an existing drug, cidofovir.

| S-EPMC5050167 | biostudies-literature

Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

Project description:We report an enantioselective coupling between α-branched aldehydes and alkynes to generate vicinal quaternary and tertiary carbon stereocenters. The choice of Rh and organocatalyst combination allows for access to all possible stereoisomers with high enantio-, diastereo-, and regioselectivity. Our study highlights the power of catalysis to activate two common functional groups and provide access to divergent stereoisomers and constitutional structures.

| S-EPMC9141309 | biostudies-literature

Amine-borane complex-initiated SF<sub>5</sub>Cl radical addition on alkenes and alkynes.

Project description:The SF5Cl radical addition on unsaturated compounds was performed using an air-stable amine-borane complex as the radical initiator. This method showed to be complementary to the classic Et3B-mediated SF5Cl addition on alkenes and alkynes. A total of seven alkene and three alkyne derivatives were tested in the reaction, with yields ranging from 3% to 85%.

| S-EPMC7753108 | biostudies-literature

Oxygen-mediated Polymerization Initiated by Oltipraz-derived Thiones.

Project description:A pyrrolopyrazine-thione derived from oltipraz, a compound that has been investigated as a chemopreventive agent, affords radicals in the presence of thiols and oxygen via a redox cycle, an attribute that suggests its suitability as an initiator for oxygen-mediated polymerization. Here, we explore the utilization of this pyrrolopyrazine-thione, generated in situ from a precursor, as an initiator for the radical-mediated thiol-ene polymerization. While the pyrrolopyrazine-thione was shown to be capable of generating radicals in the presence of atmospheric oxygen and thiol groups, the reaction extents achievable were lower than desired owing to the presence of unwanted side reactions that would quench radical production and, subsequently, suppress polymerization. Moreover, we found that complex interactions between the pyrrolopyrazine-thione, its precursor, oxygen, and thiol groups determine whether or not the quenching reaction dominates over those favorable to polymerization.

| S-EPMC5609726 | biostudies-literature

Correction: Amine-borane complex-initiated SF<sub>5</sub>Cl radical addition on alkenes and alkynes.

Project description:[This corrects the article DOI: 10.3762/bjoc.16.256.].

| S-EPMC8313978 | biostudies-literature

Synthesis and in vitro antiviral evaluation of 4-substituted 3,4-dihydropyrimidinones.

Project description:A series of 4-substituted 3,4-dihydropyrimidine-2-ones (DHPM) was synthesized, characterized by IR, 1H NMR, 13C NMR and HRMS spectra. The compounds were evaluated in vitro for their antiviral activity against a broad range of DNA and RNA viruses, along with assessment for potential cytotoxicity in diverse mammalian cell lines. Compound 4m, which possesses a long lipophilic side chain, was found to be a potent and selective inhibitor of Punta Toro virus, a member of the Bunyaviridae. For Rift Valley fever virus, which is another Bunyavirus, the activity of 4m was negligible. DHPMs with a C-4 aryl moiety bearing halogen substitution (4b, 4c and 4d) were found to be cytotoxic in MT4 cells.

| S-EPMC7127791 | biostudies-literature

Silyl Anion Initiated Hydroboration of Aldehydes and Ketones.

Project description:Hydroboration is an emerging method for mild and selective reduction of carbonyl compounds. Typically, transition-metal or reactive main-group hydride catalysts are used in conjunction with a mild reductant such as pinacolborane. The reactivity of the main-group catalysts is a consequence of the nucleophilicity of their hydride ligands. Silicon hydrides are significantly less reactive and are therefore not efficient hydroboration catalysts. Here, a readily prepared silyl anion is reported to be an effective initiator for the reduction of aldehydes and ketones requiring mild conditions, low catalyst loadings and with a good substrate scope. The silyl anion it is shown to activate HBpin to generate a reactive borohydride in situ which reacts with aldehydes and ketones to afford the hydroboration product.

| S-EPMC7496802 | biostudies-literature

An efficacious protocol for C-4 substituted 3,4-dihydropyrimidinones. Synthesis and calcium channel binding studies.

Project description:Ethyl 1,2-dihydro-1,6-dimethyl/6-methyl-2-oxopyrimidine-5-carboxylates react with C-nucleophiles as well as anion of enantiopure chiral auxiliary (1R,2S,5R)-(-)-methyl (S)-p-toluenesulfinate to afford C-4 substituted and enantiopure congeners of medicinally potent Biginelli dihydropyrimidinones. The calcium channel blocking activity of some of the compounds was evaluated and compared with nifedipine for their ability to relax a membrane depolarization induced contraction.

| S-EPMC3834990 | biostudies-literature

Nickel-Catalyzed Three-Component Cycloadditions of Enoates, Alkynes, and Aldehydes.

Project description:A method for the three-component cycloaddition of enoates, alkynes, and aldehydes has been developed. Building upon previous work by this group in which stoichiometrically generated metallacycles undergo alkylation, we report a catalytic, alkylative [3 + 2] cycloaddition. From simple starting materials, structurally complex cyclopentenones may be rapidly assembled. Computational investigation of the mechanism (ωB97X-D3/cc-pVTZ//ωB97X/6-31G(d)) identified three energetically feasible pathways. Based on the relative rates of ketene formation compared to isomerization to a seven-membered metallacycle, the most likely mechanism has been determined to occur "ketene-first", with carbocyclization prior to aldol addition. Deuterium labeling studies suggest that formation of the seven-membered metallacycle becomes possible when an α-substituted enoate is used. This observed change in selectivity is due to the increased difficulty of phenoxide elimination with the inclusion of additional steric bulk of the α-substituent. The net transformation results in a [3 + 2] cycloaddition accompanied by an alkylation of the enoate substituent.

| S-EPMC7167596 | biostudies-literature

Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts.

Project description:Prochiral ketones are reduced to enantioenriched, secondary alcohols using catecholborane and a family of air-stable, bifunctional thiourea-amine organocatalysts. Asymmetric induction is proposed to arise from the in situ complexation between the borane and chiral thiourea-amine organocatalyst resulting in a stereochemically biased boronate-amine complex. The hydride in the complex is endowed with enhanced nucleophilicity while the thiourea concomitantly embraces and activates the carbonyl.

| S-EPMC2860298 | 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