Category: Triazoles

Proton Transfer Reactions of Triazol-3-ylidenes: Kinetic Acidities and Carbon Acid pK_a Values for Twenty Triazolium Salts in Aqueous Solution was written by Massey, Richard S.;Collett, Christopher J.;Lindsay, Anita G.;Smith, Andrew D.;O’Donoghue, AnnMarie C.. And the article was included in Journal of the American Chemical Society in 2012.Electric Literature of C11H12BF4N3O The following contents are mentioned in the article:

Second-order rate constants have been determined for deuteroxide ion-catalyzed exchange of the C(3)-proton for deuterium, k_DO (M^-1 s^-1), of a series of 20 triazolium salts in aqueous solution at 25 °C and ionic strength I = 1.0 (KCl). Evidence is presented that the rate constant for the reverse protonation of the triazol-3-ylidenes by solvent water is close to that for dielec. relaxation of solvent (10¹¹ s^-1). These data enabled the calculation of carbon acid pK_a values in the range 16.5-18.5 for the 20 triazolium salts. PD rate profiles for deuterium exchange of the triazolium salts reveal that protonation at nitrogen to give dicationic triazolium species occurs under acidic conditions, with estimates of pK_a^N1 = -0.2 to 0.5. This study involved multiple reactions and reactants, such as 2-Phenyl-5,6-dihydro-8H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate (cas: 1414773-56-0Electric Literature of C11H12BF4N3O).

2-Phenyl-5,6-dihydro-8H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate (cas: 1414773-56-0) belongs to triazole derivatives. However, triazoles are also useful in bioorthogonal chemistry, because the large number of nitrogen atoms causes triazoles to react similar to azides. Triazole growth retardants such as uniconazole and paclobutrazol have been known to inhibit the biosynthesis of gibberellins by blocking kaurene oxidase, an P450 enzymeElectric Literature of C11H12BF4N3O

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Design of new small cyclic melanocortin receptor-binding peptides using molecular modeling: role of the His residue in the melanocortin peptide core was written by Prusis, Peteris;Muceniece, Ruta;Mutule, Ilze;Mutulis, Felikss;Wikberg, Jarl E. S.. And the article was included in European Journal of Medicinal Chemistry in 2001.Related Products of 156311-83-0 The following contents are mentioned in the article:

The conserved core, His-Phe-Arg-Trp, of melanocyte stimulating hormones (MSH) was probed by comparing a cyclic pentapeptide, cyclo(His-D-Phe-Arg-Trp-Gly), with three structurally similar cyclic peptides, cyclo(Asn-D-Phe-Arg-Trp-Gly), cyclo(D-Phe-Arg-Trp-Glu)-OH, and cyclo(D-Phe-Arg-Trp-Glu)-NH₂, but lacking in His. All three peptides bound to the MC₁, MC₃, MC₄ and MC₅ receptors with similar affinities. Mol. modeling indicated that the 3D structure of the DPhe-Arg-Trp of all three peptides were closely similar. The data showed that the His residue of the small rigid cyclic MSH core peptides does not participate in binding with the melanocortin receptors. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Related Products of 156311-83-0).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Among the nitrogen-containing heterocyclic compounds, triazoles emerge with superior pharmacological applications. Triazole growth retardants such as uniconazole and paclobutrazol have been known to inhibit the biosynthesis of gibberellins by blocking kaurene oxidase, an P450 enzymeRelated Products of 156311-83-0

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Peptide thioacylation with high stereochemical preservation was written by Hoeg-Jensen, Thomas;Holm, Arne;Sorensen, Hilmer. And the article was included in Synthesis in 1996.Quality Control of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) The following contents are mentioned in the article:

A dipeptide thioamide model system, Boc-Leu-ψ[CSNH]-Met-OMe, was used for evaluating the preservation of amino acid stereochem. during thioacylation utilizing amino monothio acids. The LL and DL peptide diastereomers were separated by use of high performance capillary electrophoresis (micellar electrokinetic capillary chromatog.). This thioacylation method combines monothio acids with coupling reagents of the PyBOP-family for generating active thiono esters with low-levels of enantiomerization (<2%). The best results in terms of stereochem. preservation and yield were obtained with PyNOP, a 6-nitro analog of PBOP. The successful activation of thiobenzoic acid with all 4 coupling reagents extended the scope of the method to include aryl monothio acids. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Quality Control of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V)).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Triazoles consist of a five-membered ring containing three nitrogen atoms and are biologically active, especially as antifungal, antimicrobial and enzyme inhibitors. 1,2,3-Triazoles are usually prepared following (3+2) cycloaddition protocols. A common technique for unsubstituted triazoles is the Huisgen azide-alkyne 1,3-dipolar cycloaddition: a azide and an alkyne react at high temperature to form a ring. However, the Huisgen strategy produces a mixture of isomers (typically 1,4- and 1,5-disubstituted) when used to produce substituted triazoles.Quality Control of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V)

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Highly enantioselective synthesis of fused bicyclic dihydropyranones via low-loading N-heterocyclic carbene organocatalysis was written by Li, Jun-Long;Fu, Lu;Wu, Jiao;Yang, Kai-Chuan;Li, Qing-Zhu;Gou, Xiao-Jun;Peng, Cheng;Han, Bo;Shen, Xu-Dong. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.Reference of 1631733-83-9 The following contents are mentioned in the article:

Highly diastereo and enantioselective [4+2] cycloadditions have been achieved between pyrrolidone-derived cyclic enones and α-haloaldehydes under mild conditions. Relying on extremely reactive in-situ generated chiral N-heterocyclic carbenes, this stereoselective annulation proceeded efficiently even on the gram scale with the catalyst loading as low as 0.025 mol% (250 ppm). A variety of cis-substituted bicyclic dihydropyranones can be produced in up to 96% yield with up to >99% ee. In addition, simple, inexpensive linear aldehydes such as n-propanal can be used directly in asym. cycloadditions via oxidative N-heterocyclic carbene organocatalysis with low catalyst loading. This method may provide an economical and practical approach for the asym. synthesis of medicinally relevant mols. This study involved multiple reactions and reactants, such as (S)-5-Isopropyl-2-mesityl-6,8-dihydro-5H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate (cas: 1631733-83-9Reference of 1631733-83-9).

(S)-5-Isopropyl-2-mesityl-6,8-dihydro-5H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate (cas: 1631733-83-9) belongs to triazole derivatives. The many free lone pairs in triazoles make them useful as coordination compounds, although not typically as haptic ligands. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules.Reference of 1631733-83-9

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Dynamic Kinetic Asymmetric Cross-Benzoin Additions of β-Stereogenic α-Keto Esters was written by Goodman, C. Guy;Johnson, Jeffrey S.. And the article was included in Journal of the American Chemical Society in 2014.Application of 1631733-83-9 The following contents are mentioned in the article:

The dynamic kinetic resolution of β-halo α-keto esters via an asym. cross-benzoin reaction is described. A chiral N-heterocyclic carbene catalyzes the umpolung addition of aldehydes to racemic α-keto esters. The resulting fully substituted β-halo glycolic ester products are obtained with high levels of enantio- and diastereocontrol [e.g., PhCHO + β-bromo-α-keto ester I → II in >95% conversion, > 20:1 dr, 94:6 er]. The high chemoselectivity observed is a result of greater electrophilicity of the α-keto ester toward the Breslow intermediate. The reaction products are shown to undergo highly diastereoselective substrate-controlled reduction to give highly functionalized stereotriads. This study involved multiple reactions and reactants, such as (S)-5-Isopropyl-2-mesityl-6,8-dihydro-5H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate (cas: 1631733-83-9Application of 1631733-83-9).

(S)-5-Isopropyl-2-mesityl-6,8-dihydro-5H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate (cas: 1631733-83-9) belongs to triazole derivatives. However, triazoles are also useful in bioorthogonal chemistry, because the large number of nitrogen atoms causes triazoles to react similar to azides. Both the triazoles and their derivatives have significant biological properties including antimicrobial, antiviral, antitubercular, anticancer, anticonvulsant, analgesic, antioxidant, anti-inflammatory, and antidepressant activities.Application of 1631733-83-9

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The Scope and Mechanism of Phosphonium-Mediated S_NAr Reactions in Heterocyclic Amides and Ureas was written by Wan, Zhao-Kui;Wacharasindhu, Sumrit;Levins, Christopher G.;Lin, Melissa;Tabei, Keiko;Mansour, Tarek S.. And the article was included in Journal of Organic Chemistry in 2007.Synthetic Route of C17H27F6N7OP2 The following contents are mentioned in the article:

An efficient “one-step” synthesis of cyclic amidines and guanidines has been developed. Treatment of cyclic amides and ureas, e.g. 4-quinazolinone, with benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), base, and nitrogen nucleophiles leads to the formation of the corresponding cyclic amidines and guanidines, e.g. 4-amino-substituted quinazolines, typically in good to excellent yields. This method has also been used to prepare heteroaryl ethers and thioethers using phenol and thiophenol nucleophiles. Time course NMR and HPLC-MS studies have facilitated explicit characterization of the proposed intermediates (the phosphonium salt and HOBt adduct); the data reveal a stepwise reaction pathway. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Synthetic Route of C17H27F6N7OP2).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules.Synthetic Route of C17H27F6N7OP2

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A Unified Strategy Towards N-Aryl Heterocycles by a One-Pot Copper-Catalyzed Oxidative C-H Amination of Azoles was written by Subramanian, Parthasarathi;Kaliappan, Krishna P.. And the article was included in European Journal of Organic Chemistry in 2014.Product Details of 39876-84-1 The following contents are mentioned in the article:

An efficient one-pot synthesis of N-aryl-substituted heterocycles, e.g. I (R¹ = H; R¹₂ = CH:CHCH:CH; R² = Ph, 2-pyridyl, 4-methyl-2-pyridyl, 2-naphthyl), by a Cu-catalyzed two-fold C-N bond formation is reported. This strategy involves a Cu^I-catalyzed C-N bond-forming reaction between o-aminoaryl-substituted azoles, e.g. II, and electron-deficient bromoarenes R²Br followed by an intramol. sp² C-H amination. The product I (R¹₂ = CH:CHCH:CH; R² = 6-methyl-2-pyridyl) thus formed has been successfully used as a ligand for the synthesis of a Pd complex. This study involved multiple reactions and reactants, such as 2-(1,2,4-Triazol-1-yl)aniline (cas: 39876-84-1Product Details of 39876-84-1).

2-(1,2,4-Triazol-1-yl)aniline (cas: 39876-84-1) belongs to triazole derivatives. Among the nitrogen-containing heterocyclic compounds, triazoles emerge with superior pharmacological applications. Triazoles are compounds with a vast spectrum of applications, varying from materials (polymers), agricultural chemicals, pharmaceuticals, photoactive chemicals and dyes.Product Details of 39876-84-1

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Oxidative Palladium Catalysis in S_NAr Reactions Leading to Heteroaryl Ethers from Pyridotriazol-1-yloxy Heterocycles with Aryl Boronic Acids was written by Wacharasindhu, Sumrit;Bardhan, Sujata;Wan, Zhao-Kui;Tabei, Keiko;Mansour, Tarek S.. And the article was included in Journal of the American Chemical Society in 2009.SDS of cas: 156311-83-0 The following contents are mentioned in the article:

The palladium-catalyzed oxidative coupling of pyrido- and benzotriazol-1-yloxyquinazolines and -thienopyrimidines, e.g., I, with aryl boronic acids in the presence of Pd(PPh₃)₄ and Cs₂CO₃ under oxygen in DME containing 0.4-0.8% water for the preparation of heteroaryl ethers, e.g., II, is described. These transformations of triazol-1-yloxy reagents demonstrate excellent O-chemoselective control under mild conditions and good yields. Mechanistic studies based on ¹⁸O labeling indicate that phenols as intermediates in S_NAr reactions with ethers are formed in oxidative and nonoxidative pathways. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0SDS of cas: 156311-83-0).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents. Triazoles are compounds with a vast spectrum of applications, varying from materials (polymers), agricultural chemicals, pharmaceuticals, photoactive chemicals and dyes.SDS of cas: 156311-83-0

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Incorporation of Fmoc-Dab(Mtt)-OH during solid-phase peptide synthesis: A word of caution was written by Lam, Pak-Lun;Wu, Yue;Wong, Ka-Leung. And the article was included in Organic & Biomolecular Chemistry in 2022.Category: triazoles The following contents are mentioned in the article:

As a com. available and orthogonally protected amino acid building block, Fmoc-Dab(Mtt)-OH (Fmoc = 9-fluoerenylmethoxycarbonyl, Dab = 2,4-diaminobutyric acid, Mtt = p-methyltrityl group) showed abnormally poor coupling efficiency during solid-phase peptide synthesis (SPPS). Herein, we reveal that Fmoc-Dab(Mtt)-OH undergoes rapid lactamization under a series of conditions with various coupling reagents. Although the complete incorporation of Fmoc-Dab(Mtt)-OH can be achieved using a multi-time and preincubation-free protocol with the coupling reagent DEPBT, alternative orthogonally protected building blocks are suggested to be used for avoiding such a costly and tedious procedure. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Category: triazoles).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. However, triazoles are also useful in bioorthogonal chemistry, because the large number of nitrogen atoms causes triazoles to react similar to azides. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules.Category: triazoles

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation was written by Valeur, Eric;Bradley, Mark. And the article was included in Tetrahedron in 2007.Category: triazoles The following contents are mentioned in the article:

Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition PS-IIDQ was more efficient than polymer-supported carbodiimides (PS-EDC and PS-DCC) and gave higher yields than HATU for general amide bond formation, including the coupling of anilines and hindered substrates. When evaluated with five carboxylic acids and nine amines (including anilines and secondary amines) PS-IIDQ gave an average isolated yield of 73%. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Category: triazoles).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Many triazoles are versatile, biologically active compounds commonly used as fungicides and plant retardants. The presence of the three nitrogen atoms in triazole structures afforded opportunities for a plethora of structural modification with the generation of novel therapeutically potential agents, which is different from other heterocyclic compounds.Category: triazoles

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics