36022-11-4

Usage

InChI:InChI=1/C8H6N4/c1-2-4-7(5-3-1)8-11-9-6-10-12-8/h1-6H

Upstream product

• 35011-53-1 3-bromo-6-phenyl-1,2,4,5-tetrazine 
• 832112-48-8 3-phenyl-1,4-dihydro-1,2,4,5-tetrazine 
• 5873-90-5 methyl benzimidate hydrochloride 
• 3473-63-0 formamidine acetic acid 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 825-60-5 benzimidic acid ethyl ester 
• 98-80-6 phenylboronic acid 

Downstream Products

• 83182-69-8 4-Butyl-3-phenyl-5-(trimethylsilyl)pyridazin 
• 112513-77-6 1-Methyl-9-phenyl-2,3,4,5-tetrahydro-1H-pyridazino[4,5-b]azepine 
• 78113-93-6 6-n-octylamino-3-phenyl-1,2,4,5-tetrazine 
• 83182-77-8 3-Phenyl-5-(trimethylsilyl)-4-<(trimethylsilyl)ethinyl>pyridazin 
• 32139-58-5 (4aS,4bR)-4a,4b-Dimethyl-2-phenyl-2a,2b,4a,4b-tetrahydro-cyclopropa[cd]pentalene 
• 37385-32-3 3,4-diphenylpyridazine 
• 83182-73-4 4-Acetyl-5-(trimethylsilyl)-3-phenyl-pyridazin 
• 83182-74-5 4-Propionyl-3-phenyl-5-(trimethylsilyl)pyridazin 
• 83182-78-9 3-Phenyl-5-(trimethylsilyl)-4-<6-(trimethylsilyl)-5-hexinyl>pyridazin 
• 83182-75-6 4-(1-Butinyl)-3-phenyl-5-(trimethylsilyl)pyridazin 
• 83182-70-1 4-(1-Cyclohexen-1-yl)-3-phenyl-5-(trimethylsilyl)pyridazin 
• 83182-76-7 3-Phenyl-4-(phenylethinyl)-5-(trimethylsilyl)pyridazin 
• 83182-71-2 4-(1-Cyclopenten-1-yl)-3-phenyl-5-(trimethylsilyl)pyridazin 
• 83182-72-3 4-Benzoyl-3-phenyl-5-(trimethylsilyl)pyridazin 

Relevant academic research and scientific papers

Cross-Coupling Reactions of Monosubstituted Tetrazines

A Ag-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids is presented. Electronic modification of the 1,1′-bis(diphenylphosphine)ferrocene (dppf) ligand was found to be crucial for good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were prepared (29 examples, up to 87% yield).

Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers

The nucleophilic addition of silyl-enol ethers to nitrogen in 3-monosubstituted s-tetrazines mediated by BF3 is reported. The preference for this azaphilic addition over the usually observed inverse electron demand Diels-Alder reactions was evaluated theoretically and corroborated by experiments. The substrate dependency of this unusual reaction was rationalized by determination of the activation barriers and on the basis of the activation strain model by employing density functional theory.

Boron Trifluoride-Mediated Cycloaddition of 3-Bromotetrazine and Silyl Enol Ethers: Synthesis of 3-Bromo-pyridazines

Pyridazines are important scaffolds for medicinal chemistry or crop protection agents, yet the selective preparation of 3-bromo-pyridazines with high regiocontrol remains difficult. We achieved the Lewis acid-mediated inverse electron demand Diels-Alder reaction between 3-monosubstituted s-tetrazine and silyl enol ethers and obtained functionalized pyridazines. In the case of 1-monosubstituted silyl enol ethers, exclusive regioselectivity was observed. Downstream functionalization of the resulting 3-bromo-pyridazines was demonstrated utilizing several cross-coupling protocols to synthesize 3,4-disubstituted pyridazines with excellent control over the substitution pattern.

Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction

Bioorthogonal reactions are widely used for the chemical modification of biomolecules. The application of vinylboronic acids (VBAs) as non-strained, synthetically accessible and water-soluble reaction partners in a bioorthogonal inverse electron-demand Diels–Alder (iEDDA) reaction with 3,6-dipyridyl-s-tetrazines is described. Depending on the substituents, VBA derivatives give second-order rate constants up to 27 m?1s?1in aqueous environments at room temperature, which is suitable for biological labeling applications. The VBAs are shown to be biocompatible, non-toxic, and highly stable in aqueous media and cell lysate. Furthermore, VBAs can be used orthogonally to the strain-promoted alkyne–azide cycloaddition for protein modification, making them attractive complements to the bioorthogonal molecular toolbox.

Synthesis of 3-Phenyl-5-silylpyridazines by Regioselective -Cycloadditions

The cycloaddition of 3-phenyl-1,2,4,5-tetrazine (1) with the silylethyne 2a proceeds highly regioselectively to give 3-phenyl-5-(trimethylsilyl)pyridazine (3a).Similarly the reactions of 1 with the silylalkynes 2b - f, the silylalkynones 2g - i, and the s

Aryl s tetrazines with antiinflammatory activity

Various aryl s tetrazines and benzyl s tetrazines displayed aspirin like activity when tested against carrageenan induced edema in the rat, uv induced erythema in guinea pigs, and adjuvant induced arthritis in rats. These agents also displayed analgesic activity in the mouse writhing and paw pain tests but also lowered the red blood cell count in normal healthy rats.