Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

2-Arylhydrazononitriles as building blocks in heterocyclic synthesis: A novel route to 2-substituted-1,2,3-triazoles and 1,2,3-triazolo[4,5-b]pyridines.

ABSTRACT: 2-Arylhydrazono-3-oxobutanenitriles 2 was reacted with hydroxylamine hydrochloride to yield amidooxime 3. This was cyclized into the corresponding oxadiazole 4 on refluxing in acetic anhydride. When refluxed in DMF in presence of piperidine, the corresponding 1,2,3-triazoleamine 5 was formed. The latter was acylated to 6 by addition of acetic anhydride while treatment of 5 with malononitrile gave the 1,2,3-triazolo [4,5-b]pyridine 8. Treatment of acetyl derivative 6 with DMFDMA gave enaminone 9. The enaminone 9 was coupled with benzenediazonium chloride to yield phenylazo-1,2,3-triazolo [4,5-b]pyridine 10. Trials to convert compound 14 into 1,2,3-triazolo [4,5-d]pyrimidine 15 via refluxing in AcOH/NH4OAc failed. Instead the hydrolyzed product 5 was formed.

SUBMITTER: Al-Mousawi SM

PROVIDER: S-EPMC1847523 | biostudies-literature | 2007 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

2-Arylhydrazononitriles as building blocks in heterocyclic synthesis: A novel route to 2-substituted-1,2,3-triazoles and 1,2,3-triazolo[4,5-b]pyridines.

Al-Mousawi Saleh M SM Moustafa Moustafa Sh MSh

Beilstein journal of organic chemistry 20070313

2-Arylhydrazono-3-oxobutanenitriles 2 was reacted with hydroxylamine hydrochloride to yield amidooxime 3. This was cyclized into the corresponding oxadiazole 4 on refluxing in acetic anhydride. When refluxed in DMF in presence of piperidine, the corresponding 1,2,3-triazoleamine 5 was formed. The latter was acylated to 6 by addition of acetic anhydride while treatment of 5 with malononitrile gave the 1,2,3-triazolo [4,5-b]pyridine 8. Treatment of acetyl derivative 6 with DMFDMA gave enaminone 9. ...[more]

PMID: 17355619

Similar Datasets

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

Expedited Route to Fully Substituted Amino-Pyrazole Building Blocks and Their Further Transformations.

Project description:We report here an efficient and easily reproducible two-step approach to heterocycle-substituted amino-pyrazoles from heterocyclic acetonitriles and their unprecedented subsequent transformations to fully substituted pyrazoles. Such transformations include regioselective derivatization from polyamino derivatives, formation of tetracyclic compounds in up to 45% overall yield, and deaminative transformations through diazotization, followed by arylation through Suzuki-Miyaura cross-coupling and C-H activation, providing arylated pyrazoles in up to 71% yield over four steps. This strategy allows the swift introduction of significant molecular complexity to a range of scaffolds.

| S-EPMC6645537 | 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

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

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

5-Formyltriazoles as Valuable Starting Materials for Unsymmetrically Substituted Bi-1,2,3-Triazoles.

Project description:Herein, we present the first synthetic methodologies toward non-symmetrical 5,5'-C, C-linked bi-1,2,3-triazoles starting from 5-formyl-1,2,3-triazole via two related pathways. In a first reaction, 5-formyl-1,2,3-triazole is successfully reacted with a variety of nitroalkanes and organic azides in a one-pot three-component fashion resulting in tetra-ortho-substituted bi-1,2,3-triazoles. In the second, closely related reaction, 5-formyl-1,2,3-triazole is initially converted with nitromethane to the corresponding nitroalkene, and then subsequently oxidatively cyclized with a number of organic azides toward 4-nitro substituted non-symmetrical tetra-ortho-substituted 5,5'-bi-1,2,3-triazoles. The scope of both reactions and furtherr post-functionalizations are examined, and the atropisomeric properties of the obtained bi-1,2,3-triazoles are evaluated.

| S-EPMC7174647 | biostudies-literature

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

Anti-gastric cancer activity of 1,2,3-triazolo[4,5-d]pyrimidine hybrids (1,2,3-TPH): QSAR and molecular docking approaches.

Project description:Gastric cancer as a dreaded disease which occurs in the digestive system of human being remain a threat to the medical world. Bioactivity of series of designed and synthesized molecular compounds containing triazole and pyrimidine moieties were subjected to quantum chemical calculations using B3LYP/6-31+G?. The calculated molecular descriptors such as the EHOMO (eV), ELUMO (eV), band gap (eV), chemical hardness (?), global nucleophilicity, dipole moment (Debye), chemical potential, log P, molecular weight (amu) and Ovality. The descriptors that describe anti-gastric cancer activity of the studied compounds were used for QSAR analysis using SPSS and Gretl software packages for multiple linear regression (MLR), XLSTAT for partial least square (PLS) and MATLAB for artificial neural network (ANN). The methods (MLR, PLS, and ANN) were predictive. Nevertheless, ANN performed better than MLR and PLS. More so, molecular docking study was executed on the studied compounds and gastric cancer cell line (PDB ID:4oum); the docking studies showed that 2-(1-(2-(3-benzyl-5-(benzylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)hydrazono)ethyl)phenol (A22) having the lowest binding affinity (-8.40 kcal/mol); this was correlated to the observed inhibitory activity of the compound against gastric cancer. Thus, it showed better inhibition than other studied compounds. The amino acid residues that were involved in stabilizing A22 in the active site of the 4oum are: VAL-9, ALA-10, THR-49, ASN-48, PRO-47 and TYR-46. Also, a good relationship was observed between the calculated binding affinity and the observed inhibition concentration (IC50).

| S-EPMC7090349 | biostudies-literature

Discovery of [1,2,3]Triazolo[4,5-<i>d</i>]pyrimidine Derivatives as Novel LSD1 Inhibitors.

Project description:Lysine specific demethylase 1 (LSD1) plays a pivotal role in regulating the lysine methylation. The aberrant overexpression of LSD1 has been reported to be involved in the progression of certain human malignant tumors. Abrogation of LSD1 with RNAi or small molecule inhibitors may lead to the inhibition of cancer proliferation and migration. Herein, a series of [1,2,3]triazolo[4,5-d]pyrimidine derivatives were synthesized and evaluated for their LSD1 inhibitory effects. The structure-activity relationship studies (SARs) were conducted by exploring three regions of this scaffold, leading to the discovery of compound 27 as potent LSD1 inhibitor (IC50 = 0.564 μM). Compound 27 was identified as a reversible LSD1 inhibitor and showed certain selectivity to LSD1 over monoamine oxidase A/B (MAO-A/B). When MGC-803 cells were treated with compound 27, the activity of LSD1 can be significantly inhibited, and the cell migration ability was also suppressed. Docking studies indicated that the hydrogen interaction between the nitrogen atom in the pyridine ring and Met332 could be responsible for the improved activity of 2-thiopyridine series. The [1,2,3]triazolo[4,5-d]pyrimidine scaffold can be used as the template for designing new LSD1 inhibitors.

| S-EPMC5392756 | 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