Category: Triazoles

Voitekhovich, Sergei V. published the artcileSelective complexation of 1-ethyl-5-nitro-1,2,3-triazole (entz) with copper(II) salts: Preparation and characterization of [Cu(entz)₂Cl₂] and [Cu(entz)₄(H₂O)₂](ClO₄)₂, Name: 5-Nitro-1H-1,2,3-triazole, the publication is Inorganic Chemistry Communications (2012), 77-80, database is CAplus.

Treatment of a mixture of isomeric N-ethyl-4(5)-nitro-1,2,3-triazoles with copper(II) chloride or copper(II) perchlorate was found to yield crystalline complexes with 1-ethyl-5-nitro-1,2,3-triazole (entz), namely [Cu(entz)₂Cl₂] or [Cu(entz)₄(H₂O)₂](ClO₄)₂, resp. The obtained complexes, being the rare examples of coordination compounds of vicinal nitrotriazoles, have been characterized by X-ray diffraction and thermal methods. Both compounds present mononuclear complexes with entz coordinating through N3 atom of heterocycle. The complexes are readily decomposed under action of aqueous ammonia generating pure 1-ethyl-5-nitro-1,2,3-triazole with high yield. Succession of complexation and decomplexation reactions was shown to be a simple procedure for isolation of 1-ethyl-5-nitro-1,2,3-triazole from isomeric mixtures formed under alkylation of 4-nitro-1,2,3-triazole.

Inorganic Chemistry Communications published new progress about 14544-45-7. 14544-45-7 belongs to triazoles, auxiliary class Triazoles, name is 5-Nitro-1H-1,2,3-triazole, and the molecular formula is C11H10O, Name: 5-Nitro-1H-1,2,3-triazole.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Sukhanov, Gennady T. published the artcileAcidic N-dealkylation in nitrotriazolium salts, SDS of cas: 14544-45-7, the publication is Mendeleev Communications (2022), 32(2), 215-217, database is CAplus.

New selective synthesis of 1-alkyl-4-nitro-1,2,3-triazoles I [R¹ = Me, Et, Bn, etc.] and 1-alkyl-5-nitro-1,2,3-triazoles II [R² = Me, Et, n-Bu, etc.] had been developed, involving acid N-dealkylation of 1,3-dialkyl-4-nitro-1,2,3-triazolium salts III. The assortment of novel 1-alkyl-4(5)-nitro-1,2,3-triazoles had been thus essentially expanded. Treatment of relative 3-nitro-1,2,4-triazolium salts IV [R³ = H, Me; R⁴ = Me, Et, t-Bu; R⁵ = Me, Et] with HCl or HBr proceeded mostly as S^ipso_N-substitution of the nitro group.

Mendeleev Communications published new progress about 14544-45-7. 14544-45-7 belongs to triazoles, auxiliary class Triazoles, name is 5-Nitro-1H-1,2,3-triazole, and the molecular formula is C44H28ClFeN4, SDS of cas: 14544-45-7.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Sukhanov, Gennady T. published the artcileSynthesis of 1-(Adamantan-1-yl)-1H-1,2,3-Triazoles and their Salts by Adamantylation in AdOH-HClO₄ and AdOH-H₂SO₄ Systems, COA of Formula: C2H2N4O2, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2019), 55(12), 1197-1203, database is CAplus.

1-(Adamantan-1-yl)-1H-1,2,3-triazoles and a series of 1-(adamantan-1-yl)-3-alkyl-1,2,3-triazolium salts were synthesized by regioselective adamantylation of 1,2,3-triazole derivatives The direction of the attack by the adamantyl cation at the N-1 nitrogen atom and the regioselectivity of the processes of adamantylation and quaternization were ensured by a number of factors: the specificity of the properties of the high-acid systems AdOH-HClO₄ and AdOH-H₂SO₄, as well as the structural aspect and high reactivity of adamantan-1-ol.

Chemistry of Heterocyclic Compounds (New York, NY, United States) published new progress about 14544-45-7. 14544-45-7 belongs to triazoles, auxiliary class Triazoles, name is 5-Nitro-1H-1,2,3-triazole, and the molecular formula is C10H16O2, COA of Formula: C2H2N4O2.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Abboud, Jose-Luis M. published the artcileBasicity of N-H- and N-methyl-1,2,3-triazoles in the gas phase, in solution, and in the solid state – an experimental and theoretical study, Recommanded Product: 5-Nitro-1H-1,2,3-triazole, the publication is European Journal of Organic Chemistry (2001), 3013-3024, database is CAplus.

The gas-phase and aqueous basicities of six 1,2,3-triazoles have been determined, the former by FT-ICR and the latter by spectrophotometry and ¹H NMR. The gas-phase experiments agree very well with the Gibbs free energies calculated at the B3LYP/6-31G^* level. In contrast, only semiquant. ascertainments are possible when basicities in the gas phase and in solution are compared. It is possible, with the aid of calculations, to obtain a complete picture of the complex equilibrium involved in C-substituted N-H-1,2,3-triazoles. The crystal structures of 4(5)-phenyl-1,2,3-triazole (4) and 4(5)-nitro-1,2,3-triazole (15) have been determined In the gas phase, 2H tautomers b always predominate, while in aqueous solution, both 1H and 2H tautomers – a and b – are present. Finally, in the solid state, 1,2,3-triazole 1 exists as a 1:1 tautomer mixture , while 4 and 15 exist as single tautomeric structures.

European Journal of Organic Chemistry published new progress about 14544-45-7. 14544-45-7 belongs to triazoles, auxiliary class Triazoles, name is 5-Nitro-1H-1,2,3-triazole, and the molecular formula is C2H2N4O2, Recommanded Product: 5-Nitro-1H-1,2,3-triazole.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Abboud, Jose-Luis M. published the artcileBasicity of N-H- and N-methyl-1,2,3-triazoles in the gas phase, in solution, and in the solid state – an experimental and theoretical study, Safety of 4-Nitro-2H-1,2,3-triazole, the publication is European Journal of Organic Chemistry (2001), 3013-3024, database is CAplus.

The gas-phase and aqueous basicities of six 1,2,3-triazoles have been determined, the former by FT-ICR and the latter by spectrophotometry and ¹H NMR. The gas-phase experiments agree very well with the Gibbs free energies calculated at the B3LYP/6-31G^* level. In contrast, only semiquant. ascertainments are possible when basicities in the gas phase and in solution are compared. It is possible, with the aid of calculations, to obtain a complete picture of the complex equilibrium involved in C-substituted N-H-1,2,3-triazoles. The crystal structures of 4(5)-phenyl-1,2,3-triazole (4) and 4(5)-nitro-1,2,3-triazole (15) have been determined In the gas phase, 2H tautomers b always predominate, while in aqueous solution, both 1H and 2H tautomers – a and b – are present. Finally, in the solid state, 1,2,3-triazole 1 exists as a 1:1 tautomer mixture , while 4 and 15 exist as single tautomeric structures.

European Journal of Organic Chemistry published new progress about 84406-63-3. 84406-63-3 belongs to triazoles, auxiliary class Triazole,Nitro Compound, name is 4-Nitro-2H-1,2,3-triazole, and the molecular formula is C2H2N4O2, Safety of 4-Nitro-2H-1,2,3-triazole.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Zhang, Zhiqiang published the artcileSynthesis and antifungal activities of novel triazole derivatives with dithiocarbamates side chain, Formula: C12H13F2N3O4S, the publication is Yaoxue Fuwu Yu Yanjiu (2016), 16(2), 94-97, database is CAplus.

Objective: To synthesize a series of novel triazole derivatives with dithiocarbamates side chain and evaluate their antifungal activities. Methods: Nine target compounds were synthesized and their structure characterizations were conformed by ¹H-NMR and MS spectra. The in vitro antifungal activities of all the compounds were evaluated against eight human pathogenic fungi. Results: Potent antifungal activities were exhibited in all the target compounds, some of which showed potent antifungal activity against Candida glabrata (sown in I and II as examples), which was superior to such control drugs as fluconazole. Conclusion: The target compounds with dithiocarbamates side chain have potent antifungal activity.

Yaoxue Fuwu Yu Yanjiu published new progress about 86386-77-8. 86386-77-8 belongs to triazoles, auxiliary class Epoxides,Triazole,Fluoride,Salt,Sulfonic acid,Benzene, name is 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazole methanesulfonate, and the molecular formula is C20H17FO4S, Formula: C12H13F2N3O4S.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

El-Faham, Ayman published the artcileCOMU: A Safer and More Effective Replacement for Benzotriazole-Based Uronium Coupling Reagents, Application In Synthesis of 1082951-62-9, the publication is Chemistry – A European Journal (2009), 15(37), 9404-9416, S9404/1-S9404/34, database is CAplus and MEDLINE.

The authors describe a new family of uronium-type coupling reagents that differ in their iminium moieties and leaving groups. The presence of the morpholino group in conjunction with an oxime derivative, especially Et 2-cyano-2-(hydroxyimino)acetate (Oxyma), had a marked influence on the solubilities, stabilities, and reactivities of the reagents. Finally, the new uronium salt I (COMU) derived from Oxyma performed extremely well in the presence of only 1 equiv of base, thereby confirming the effect of the hydrogen bond acceptor in the reaction. I also showed a less hazardous safety profile than the benzotriazole-based HDMA and HDMB, which exhibited unpredictable autocatalytic decompositions Furthermore, the Oxyma moiety contained in I suggests a lower risk of explosion than in the case of the benzotriazole derivatives

Chemistry – A European Journal published new progress about 1082951-62-9. 1082951-62-9 belongs to triazoles, auxiliary class Active Esterification, name is 5-Chloro-1-((dimethyliminio)(morpholino)methyl)-1H-benzo[d][1,2,3]triazole 3-oxide hexafluorophosphate(V), and the molecular formula is C13H17ClF6N5O2P, Application In Synthesis of 1082951-62-9.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Eddy, Matthew T. published the artcileExtrinsic Tryptophans as NMR Probes of Allosteric Coupling in Membrane Proteins: Application to the A_2A Adenosine Receptor, HPLC of Formula: 377727-87-2, the publication is Journal of the American Chemical Society (2018), 140(26), 8228-8235, database is CAplus and MEDLINE.

Tryptophan indole ¹⁵N-¹H signals are well separated in NMR spectra of proteins. Assignment of the indole ¹⁵N-¹H signals therefore enables one to obtain site-specific information on complex proteins in supramacromol. systems, even when extensive assignment of backbone ¹⁵N-¹H resonances is challenging. Here the authors exploit the unique indole ¹⁵N-¹H chem. shift by introducing extrinsic tryptophan reporter residues at judiciously chosen locations in a membrane protein for increased coverage of structure and function by NMR. The authors demonstrate this approach with three variants of the human A_2A adenosine receptor (A_2AAR), a class A G protein-coupled receptor, each containing a single extrinsic tryptophan near the receptor intracellular surface, in helix V, VI, or VII, resp. The authors show that the native A_2AAR global protein fold and ligand binding activity are preserved in these A_2AAR variants. The indole ¹⁵N-¹H signals from the extrinsic tryptophan reporter residues show different responses to variable efficacy of drugs bound to the receptor orthosteric cavity, and the indole ¹⁵N-¹H chem. shift of the tryptophan introduced at the intracellular end of helix VI is sensitive to conformational changes resulting from interactions with a polypeptide from the carboxy terminus of the Gα_S intracellular partner protein. Introducing extrinsic tryptophans into proteins in complex supramol. systems thus opens new avenues for NMR investigations in solution

Journal of the American Chemical Society published new progress about 377727-87-2. 377727-87-2 belongs to triazoles, auxiliary class GPCR/G Protein,Adenosine Receptor, name is 2-(Furan-2-yl)-7-(2-(4-(4-(2-methoxyethoxy)phenyl)piperazin-1-yl)ethyl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine, and the molecular formula is C25H29N9O3, HPLC of Formula: 377727-87-2.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Carlsen, Per published the artcileThermal rearrangement of 4-alkyl-1,2,4-triazoles. Rearrangements in the crystalline state, Recommanded Product: 4H-1,2,4-Triazole, the publication is Molecules [Electronic Publication] (1996), 242-250, database is CAplus.

A review and symposium lecture on the thermolyses of 4-alkyl-1,2,4-triazoles with 16 references They were observed to rearrange at 200-350° to the corresponding 1-alkylated triazoles. When substituted in the 4-position with aryl or vinylic substituents, the triazoles were inert to thermolysis, contrary to what was observed for the 4-alkyl- and 4-allyl-substituted systems. The mechanisms for the reactions were elucidated, e.g., by studies of substituent effects and by kinetic measurements in solution as well as for the neat samples. Reactions in solution were slow. The rearrangements in melts of the neat triazoles readily proceeded to the products, and were proposed to take place via a series of nucleophilic displacement steps. X-ray crystallog. measurements of selected structures showed that the interat. distances and angles between the relevant atoms in these structures to a large degree resembled the geometry expected for the S_N2-type transition states proposed for the rearrangement mechanism. Thus, thermolyses of a series of triazole structures at temperatures below their m.ps., confirmed that rearrangements actually did take place. The “kinetics” of the reactions in the crystalline state were investigated, and rate constants and thermodn. data were correlated with the structural characteristics of the crystals.

Molecules [Electronic Publication] published new progress about 63598-71-0. 63598-71-0 belongs to triazoles, auxiliary class Triazole, name is 4H-1,2,4-Triazole, and the molecular formula is C2H3N3, Recommanded Product: 4H-1,2,4-Triazole.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics

Al-Azmi, Amal published the artcileNovel 2H-1,2,3-triazole sodium complex from N-[2-amino-1,2-dicyanovinyl]alkanamides, Category: triazoles, the publication is Heterocycles (2007), 71(10), 2183-2201, database is CAplus.

Diazotization at 0 °C of N-[2-amino-1,2-dicyanovinyl]ethanamide or the propanamide analog prepared from diaminomaleonitrile (DAMN) I using aqueous acetic acid and NaNO₂ solution furnished sodium complex II. The x-ray structure of the complex II showed that it is a 1:1 mixture of the neutral 2H-triazole heterocycle III and its anion deprotonated at the central (N) atom of the ring, together with a sodium counterion and two coordinated water mols. However, when the diazotization reaction was carried out in the presence of aqueous HCl, the product was 5-cyano-2H-[1,2,3]triazole-4-carboxylic acid amide monohydrate III. Diazotization of I using aqueous HCl furnished 1H-1,2,3-triazole-4,5-dicarbonitrile IV, whereas with acetic acid there was no reaction, and hence no route analogous to that leading to complex II. The structure of both complex II and the triazole monohydrate III were solved using x-ray crystallog., and the compounds under study were fully characterized using spectroscopic techniques.

Heterocycles published new progress about 53817-16-6. 53817-16-6 belongs to triazoles, auxiliary class Triazoles, name is 1H-1,2,3-Triazole-4,5-dicarbonitrile, and the molecular formula is C4HN5, Category: triazoles.

Referemce:
https://en.wikipedia.org/wiki/1,2,3-Triazole,
Triazoles – an overview | ScienceDirect Topics