Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Fused tetrazoles as azide surrogates in click reaction: efficient synthesis of N-heterocycle-substituted 1,2,3-triazoles.

ABSTRACT: It has been shown that various pyrido-, quinolino-, pyrazino-, and quinoxalinotetrazoles can be used efficiently as azide components in Cu-catalyzed click reaction with alkynes. This method allows for efficient synthesis of a wide variety of N-heterocyclic derivatives of 1,2,3-triazoles.

SUBMITTER: Chattopadhyay B

PROVIDER: S-EPMC2862078 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Fused tetrazoles as azide surrogates in click reaction: efficient synthesis of N-heterocycle-substituted 1,2,3-triazoles.

Chattopadhyay Buddhadeb B Vera Claudia I Rivera CI Chuprakov Stepan S Gevorgyan Vladimir V

Organic letters 20100501 9

It has been shown that various pyrido-, quinolino-, pyrazino-, and quinoxalinotetrazoles can be used efficiently as azide components in Cu-catalyzed click reaction with alkynes. This method allows for efficient synthesis of a wide variety of N-heterocyclic derivatives of 1,2,3-triazoles. ...[more]

PMID: 20380424

Similar Datasets

Zinc mediated azide-alkyne ligation to 1,5- and 1,4,5-substituted 1,2,3-triazoles.

Project description:A mild method for regioselective formation of 1,5-substituted 1,2,3-triazoles is described. The zinc-mediated reaction works at room temperature and is successful across a wide range of azido/alkynyl substrates. Additionally, the triazole 4-position can be further functionalized through the intermediate aryl-zinc to accommodate a diverse three-component coupling strategy.

| S-EPMC4331842 | biostudies-literature

Protein prosthesis: 1,5-disubstituted[1,2,3]triazoles as cis-peptide bond surrogates.

Project description: Not available

| S-EPMC2531141 | biostudies-literature

Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles.

Project description:Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles.

| S-EPMC3224851 | biostudies-literature

Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction.

Project description:A new monophosphine Cu(I) complex bearing bis(pyrazolyl)methane (L 1 ) (CuIL 1 PPh 3 ) was synthesized and used as a catalyst for the three-component click reaction from an alkyl halide, sodium azide, and terminal alkyne to furnish 1,4-disubstituted 1,2,3-triazoles in up to 93% yield. The catalyst is highly stable, compatible with oxygen/water, and works with total efficiency under ultrasonic condition. The structure of the complex was studied and confirmed by X-ray crystallography, finding a riveting relationship with its catalytic activity. This sustainable triazoles synthesis is distinguished by its high atom economy, low catalyst loading (up to 0.5 mol %), broad substrate scope, short reaction times, operational simplicity, and an easy gram-scale supply of a functionalized product for subsequent synthetic applications.

| S-EPMC7689893 | biostudies-literature

Click chemistry towards thermally reversible photochromic 4,5-bisthiazolyl-1,2,3-triazoles.

Project description:Three new diarylethenes were synthesized from 1,2-bis(5-methyl-2-(4-substituted-phenyl)thiazol-4-yl)ethyne and benzyl azide through Ru(I)-catalyzed Huisgen cyclization reactions. The 4,5-bisthiazolyl-1,2,3-triazoles thus prepared, which belong to the terarylene family, showed thermally reversible photochromism. The absorption maximum wavelengths of the closed forms are longer than other terarylenes reported so far. The thermal back reactions are much faster when the substituents on the terminal phenyl groups are electron-withdrawing cyano groups than when they are electron-donating methoxy groups.

| S-EPMC6753672 | biostudies-literature

Synthesis of Fused Bicyclic [1,2,3]-Triazoles from γ-Amino Diazoketones.

Project description:Triazoles are an important class of N-heterocycles that are well known for their broad biological activities. In this work, we would like to demonstrate a direct synthesis of the rare fused bicyclic [1,2,3]-triazoles, employing γ-N-protected amino diazoketones as useful synthetic platforms. The strategy was based on the deprotection of a trifluoroacetamide group for the intramolecular and in situ generation of an α-diazo imine intermediate, followed by a 5-endo-dig cyclization to construct the bicyclic unit. In this fashion, the synthesis of a series of fused bicyclic [1,2,3]-triazoles could be carried out in good to excellent yields (63-95%).

| S-EPMC6648081 | biostudies-literature

Substituted 1,2,3-triazoles: a new class of nitrification inhibitors.

Project description:Nitrogen (N) fertilisers amended with nitrification inhibitors can increase nitrogen use efficiencies in agricultural systems but the effectiveness of existing commercial inhibitor products, including 3,4-dimethylpyrazole phosphate (DMPP), is strongly influenced by climatic and edaphic factors. With increasing pressure to reduce the environmental impact of large-scale agriculture it is important to develop new nitrogen-stabilising products that can give reliable and consistent results, particularly for warmer climatic conditions. We synthesised a library of 17 compounds featuring a substituted 1,2,3-triazole motif and performed laboratory incubations in two south-eastern Australian soils. In the neutral (pH 7.3) soil, the compounds N002, N013, N016 and N017, which possess short non-polar alkyl or alkynyl substituents at the triazole ring, retained NH4+-N concentrations at 35 °C soil temperature to a better extent (P < 0.001) than DMPP. In the alkaline soil (pH 8.8) N013 performed better with regards to NH4+-N retention (P = 0.004) than DMPP at 35 °C soil temperature. Overall, our data suggest that substituted 1,2,3-triazoles, which can be synthesized with good yields and excellent atom economy through 1,3-dipolar cycloaddition from readily available starting materials, are promising nitrification inhibitors performing similar to, or better than DMPP, particularly at elevated soil temperatures.

| S-EPMC8298478 | biostudies-literature

Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles.

Project description:The 1-substituted-4-imino-1,2,3-triazole motif is an established component of coordination compounds and bioactive molecules, but depending on the substituent identity, it can be inherently unstable due to Dimroth rearrangements. This study examined parameters governing the ring-degenerate rearrangement reactions of 1-substituted-4-imino-1,2,3-triazoles, expanding on trends first observed by L'abbé et al. The efficiency of condensation between 4-formyltriazole and amine reactants as well as the propensity of imine products towards rearrangement was each strongly influenced by the substituent identity. It was observed that unsymmetrical condensation reactions conducted at 70 °C produced up to four imine products via a dynamic equilibrium of condensation, rearrangement and hydrolysis steps. Kinetic studies utilizing 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbaldehyde with varying amines showed rearrangement rates sensitive to both steric and electronic factors. Such measurements were facilitated by a high throughput colorimetric assay to directly monitor the generation of a 4-nitroaniline byproduct.

| S-EPMC6122373 | biostudies-literature

Energetic Materials Based on N-substituted 4(5)-nitro-1,2,3-triazoles.

Project description:The regularities and synthetic potentialities of the alkylation of 4(5)-nitro-1,2,3-triazole in basic media were explored, and new energetic ionic and nitrotriazole-based coordination compounds were synthesized in this study. The reaction had a general nature and ended with the formation of N1-, N2-, and N3-alkylation products, regardless of the conditions and reagent nature (alkyl- or aryl halides, alkyl nitrates, dialkyl sulfates). This reaction offers broad opportunities for expanding the variability of substituents on the nitrotriazole ring in the series of primary and secondary aliphatic, alicyclic, and aromatic substituents, which is undoubtedly crucial for solving the problems related to both high-energy materials development and medicinal chemistry when searching for new efficient bioactive compounds. An efficient methodology for the separation of regioisomeric N-alkyl(aryl)nitrotriazoles has been devised and relies on the difference in their basicity and reactivity during quaternization and complexation reactions. Based on the inaccessible N3-substitution products that exhibit a combination of properties of practical importance, a series of energy-rich ionic systems and coordination compounds were synthesized that are gaining ever-increasing interest for the chemistry of energy-efficient materials, coordination chemistry, and chemistry of ionic liquids.

| S-EPMC8838066 | biostudies-literature

Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction.

Project description:A practical and high-yielding Schmidt reaction for the synthesis of fused tetrazoles from bile acid precursors was developed. Mild reaction conditions using TMSN3 instead of hydrazoic acid as an azide source produced good yields of the desired tetrazoles. These conditions could be applied to other steroidal precursors. Additionally, an improved methodology for the synthesis of different ketone and enone precursors from cholic acid, deoxycholic acid, and chenodeoxycholic acid was established. Newly obtained tetrazole derivatives were characterized by NMR and X-ray diffraction spectroscopy. In a number of cases, preliminary antiproliferative tests of new compounds showed strong and selective activity towards certain tumor cell lines.

| S-EPMC8551880 | 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