Browse
Submit Data
Databases
API
Help

Dataset Information

14 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

α-Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1-(Dialkylamino)-1,2,3-triazoles.

ABSTRACT: The one-pot synthesis of a series of sulfonium salts containing transferable diazomethyl groups is described, and the structure of these compounds is elucidated by X-ray crystallography. Under photochemical conditions, reaction of these salts with N,N-dialkyl hydrazones affords 1-(dialkylamino)-1,2,3-triazoles via diazomethyl radical addition to the azomethine carbon followed by intramolecular ring closure. The straightforward transformation of the structures thus obtained into mesoionic carbene-metal complexes is also reported and the donor properties of these new ligands characterized.

SUBMITTER: Li X

PROVIDER: S-EPMC8048477 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Synthesis of deuterated 1,2,3-triazoles.

Project description:The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH(2)Cl(2)/D(2)O, using the CuSO(4)/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H(2)O and D(2)O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H(+) and D(+) ion concentrations in H(2)O and D(2)O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.

| S-EPMC3543115 | biostudies-literature

Efficient synthesis of 1-sulfonyl-1,2,3-triazoles.

Project description:An efficient room-temperature method for the synthesis of 1-sulfonyl-1,2,3-triazoles from in situ generated copper(I) acetylides and sulfonyl azides is described. The copper(I) thiophene-2-carboxylate (CuTC) catalyst produces the title compounds under both nonbasic anhydrous and aqueous conditions in good yields.

| S-EPMC2982995 | biostudies-literature

Tandem synthesis of 1-formyl-1,2,3-triazoles.

Project description:A tandem method for preparing 4-formyl-1,2,3-triazoles via a two-step one-pot acetal cleavage/CuAAC reaction was developed. Using this method, 4-formyl-1,2,3-triazole analogs with both electron-withdrawing and electron-donating substituents were prepared in good yield and purity. Expansion of this method to a three-step tandem reaction that incorporates an additional step of azide substitution was also successful, circumventing the need for organic azide isolation. This one-pot method, noteworthy in its simplicity and mild conditions, utilizes practical, readily available reactants and relies on protic solvent to promote acid-catalyzed acetal cleavage.

| S-EPMC5798646 | biostudies-literature

Transition-metal-free catalytic synthesis of 1,5-diaryl-1,2,3-triazoles.

Project description:1,5-Diarylsubstituted 1,2,3-triazoles are formed in high yield from aryl azides and terminal alkynes in DMSO in the presence of catalytic tetraalkylammonium hydroxide. The reaction is experimentally simple, does not require a transition-metal catalyst, and is not sensitive to atmospheric oxygen and moisture.

| S-EPMC2946857 | 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

Synthesis and reactivity of sulfamoyl azides and 1-sulfamoyl-1,2,3-triazoles.

Project description:Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of a CuTC catalyst forming 1-sulfamoyl-1,2,3-triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins.

| S-EPMC3224852 | biostudies-literature

Synthesis, antimicrobial evaluation and docking studies of fluorinated imine linked 1,2,3-triazoles

Project description:A diverse series of imine linked 1,2,3-triazole hybrids has been synthesized via Cu(I)-promoted click reaction, with an aim to develop some new antimicrobial molecules. The structural characterization of the synthesized triazole hybrids was accomplished using various spectral techniques like 1H NMR, 13C NMR, FTIR and HRMS. Among the synthesized hybrids, 7d exhibited highest antimicrobial efficacy against R. oryzae and S. aureus with MIC of 0.0123 µmol/mL and 0.0061 µmol/mL, respectively. Docking studies of the terminal alkynes (4a, 4b) and triazole hybrids (6a, 6d, 7c, 7g) showing high potency towards E. coli DNA gyrase and C. albicans sterol 14-α demethylase were also undertaken to understand the binding behaviour. Graphical abstract Supplementary Information The online version contains supplementary material available at 10.1007/s11164-022-04737-2.

| S-EPMC9146814 | biostudies-literature

Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides.

Project description:An efficient method to prepare organomagnesium intermediates having a protected azido group is reported. Protection of azido groups with di-(tert-butyl)(4-(dimethylamino)phenylphosphine (amphos) and following iodine-magnesium exchange realized the preparation of organomagnesium intermediates, which served in the synthesis of diverse azides by transformation with various electrophiles followed by deprotection with elemental sulfur. Furthermore, click reactions of azides with alkynes enabled synthesizing a wide variety of 1,2,3-triazoles.

| S-EPMC10424848 | biostudies-literature

'Click chemistry' synthesis of 1-(?-D-mannopyranosyl)-1,2,3-triazoles for inhibition of ?-mannosidases.

Project description:Three new triazole conjugates derived from d-mannose were synthesized and assayed in in vitro assays to investigate their ability to inhibit ?-mannosidase enzymes from the glycoside hydrolase (GH) families 38 and 47. The triazole conjugates were more selective for a GH47 ?-mannosidase (Aspergillus saitoi ?1,2-mannosidase), showing inhibition at the micromolar level (IC50 values of 50-250 ?M), and less potent towards GH38 mannosidases (IC50 values in the range of 0.5-6 mM towards jack bean ?-mannosidase or Drosophila melanogaster lysosomal and Golgi ?-mannosidases). The highest selectivity ratio [IC50(GH38)/IC50(GH47)] of 100 was exhibited by the phenyltriazole conjugate. To understand structure-activity properties of synthesized compounds, 3-D complexes of inhibitors with ?-mannosidases were built using molecular docking calculations.

| S-EPMC4382718 | biostudies-literature

Copper-catalyzed CuAAC/intramolecular C-H arylation sequence: Synthesis of annulated 1,2,3-triazoles.

Project description:Step-economical syntheses of annulated 1,2,3-triazoles were accomplished through copper-catalyzed intramolecular direct arylations in sustainable one-pot reactions. Thus, catalyzed cascade reactions involving [3 + 2]-azide-alkyne cycloadditions (CuAAC) and C-H bond functionalizations provided direct access to fully substituted 1,2,3-triazoles with excellent chemo- and regioselectivities. Likewise, the optimized catalytic system proved applicable to the direct preparation of 1,2-diarylated azoles through a one-pot C-H/N-H arylation reaction.

| S-EPMC3511011 | 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