14478-73-0

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 1463, 1962 DOI: 10.1021/jo01051a521Tetrahedron Letters, 16, p. 4527, 1975

InChI:InChI=1/C14H12N4/c1-3-7-11(8-4-1)13-15-17-14(18-16-13)12-9-5-2-6-10-12/h1-10H,(H,15,16)(H,17,18)

Upstream product

• 100-47-0 benzonitrile 
• 825-60-5 benzimidic acid ethyl ester 
• 302-01-2 hydrazine 
• 7803-57-8 hydrazine hydrate 
• 2227-79-4 benzenecarbothioamide 
• 6830-78-0 3,6-diphenyl-1,2,4,5-tetrazine 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 2032-36-2 Thiobenzmorpholid 
• 4111-54-0 lithium diisopropyl amide 
• 816-43-3 lithium diethylamide 
• 20915-80-4 3,4-Dihydro-6-methoxy-2-(pyrrolidin-1-yl)naphthalene 
• 98-88-4 benzoyl chloride 
• 117237-76-0 N-Methyl-2-phenylbenzotellurazolium iodide 
• 787-84-8 N'-benzoylbenzohydrazide 

Downstream Products

• 6830-78-0 3,6-diphenyl-1,2,4,5-tetrazine 
• 2039-06-7 3,5-diphenyl-1,2,4-triazole 
• 3049-45-4 4-amino-3,5-diphenyl-4H-1,2,4-triazole 
• 725-12-2 2,5-bis-(phenyl)-1,3,4-oxadiazole 
• 3026-70-8 N-(3,5-diphenyl-[1,2,4]triazol-4-yl)-diacetamide 
• 54413-55-7 4-amino-1-methyl-3,5-diphenyl-[1,2,4]triazolium; iodide 
• 68629-76-5 5,6,7,8,9,10-Hexahydro-1,4-diphenylcycloocta<1,2-d>pyridazin 
• 1355176-96-3 C₂₄H₂₄N₂O 
• 1609084-72-1 1-pivaloyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine 

Relevant academic research and scientific papers

Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives

Fourteen compounds of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives were prepared and their structures were confirmed by single-crystal X-ray diffraction and the semi-empirical calculation of PM3 method. This reaction yields the 1,4-dihydro derivatives rather than the 1,2-dihydro derivatives. The central six-membered ring of 1,4-dihydro-1,2,4,5-tetrazine has a chair conformation and therefore is not homoaromatic. Their antitumor activities were evaluated in vitro by SRB method for A-549 and BEL-7402 cells, and MTT method for P-388 and HL-60 cells. The results show that there is one compound which is highly effective against P-388 cells and one compound which is highly effective against HL-60 cells. So it is a kind of compound which possesses potential antitumor activities and is worth to research further.

Synthesis, structure analysis, antitumor evaluation and 3D-QSAR studies of 3,6-disubstituted-dihydro-1,2,4,5-tetrazine derivatives

3,6-Diaryl-dihydro-1,2,4,5-tetrazine derivatives were synthesized and their structures were confirmed by single-crystal X-ray diffraction. Monosubstituted dihydrotetrazines are the 1,4-dihydro structure, but disubstituted dihydrotetrazines are the 1,2-dihydro structure. The results of further research indicated there may be a rearrangement during the synthesis process of disubstituted dihydrotetrazines. Their antitumor activities were evaluated against A-549 and P388 cells in vitro. The results showed several compounds to be endowed with cytotoxicity in the low micromolar range. Two compounds were highly effective against A-549 cell and IC50 values were 0.575 and 2.08 μM, respectively. Three-dimensional quantitative structure-activity relationship (3D-QSAR) studies of comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were carried out on 37 1,2,4,5-tetrazine derivatives with antitumor activity against A-549 cell. Models with good predictive abilities were generated with the cross validated q2 values for CoMFA and CoMSIA being 0.744 and 0.757, respectively. Conventional r2 values were 0.978 and 0.988, respectively, the predicted R2 values were 0.916 and 0.898, respectively. The results provide the tool for guiding the design and synthesis of novel and more potent tetrazine derivatives.

Synthesis and structure analysis of 1-propionyl-3,6-diphenyl-1,4-dihydro-1, 2,4,5-tetrazine

1-Propionyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine was prepared from propionic anhydride and 3,6-diphenyl- 1,4(or 1,2)-dihydro-1,2,4,5-tetrazine, and its structure was determined by X-ray diffraction. This reaction yields the title compound rather tha

Microporous material based on π-π Stacking of 1,4-bis(3,6- diphenylpyridazin-4-yl)benzene

A microporous material constructed by π-π interaction of a twisted H-shape poly-aromatic molecule, 1,4-bis(3,6-diphenylpyridazin-4-yl)benzene (1) was synthesized and X-ray quality crystals were isolated. The intermolecular distances between the various ar

Reaction of thiourea S,S-dioxides with dyes containing carbonyl or azo groups

The kinetics of decomposition of thiourea and N-methylthiourea S,S-dioxides in alkaline aqueous medium and their reactions with oxygen, Indigo Carmine, and Acid Yellow 11 were studied. The decomposition of thiourea S,S-dioxides in weakly alkaline media was found to follow two pathways leading to the formation of ammonia and sulfoxylate ion, respectively. The second pathway predominates in strongly alkaline media. Thiourea S,S-dioxides can be used for selective reduction of azo compounds to the corresponding hydrazo derivatives. Nauka/Interperiodica 2006.

Scandium ion-promoted reduction of heterocyclic N = N double bond. Hydride transfer vs electron transfer

Hydride transfer from 10-methyl-9,10-dihydroacridine (AcrH2) to 3,6-diphenyl-1,2,4,5-tetrazine (Ph2Tz), which contains a N=N double bond, occurs efficiently in the presence of Sc(OTf)3 (OTf = OSO2-CF3

Redox potential tuning of s-tetrazine by substitution of electron-withdrawing/donating groups for organic electrode materials

Herein, we tune the redox potential of 3,6-diphenyl-1,2,4,5-tetrazine (DPT) by introducing various electron-donating/withdrawing groups (methoxy, t-butyl, H, F, and trifluoromethyl) into its two peripheral benzene rings for use as electrode material in a

3,6-Substituted-1,2,4,5-tetrazines: Tuning reaction rates for staged labeling applications

Cycloaddition reactions involving tetrazines have proven to be powerful bioorthogonal tools for various applications. Conceivably, sequential and selective labeling using tetrazine-based reactions can be achieved by tuning the reaction rate. By varying th

Synthesis, crystal structures and quantum chemical calculations of 3,6-diphenyl-1,2-dihydro- and 1,4-dihydro-1,2,4,5-tetrazine derivatives

1-Acyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazines were prepared by treatment of 3,6-diphenyl-1,4- (or 1,2)-dihydro-1,2,4,5-tetrazine and an equimolar amount of an acyl chloride. Further reaction with another equivalent of an acyl chloride yielded 1,4(or

A general and efficient entry to asymmetric tetrazines for click chemistry applications

The importance of click chemistry is widely recognized. Among all the known click reactions, those involving tetrazines represent the fastest click reactions reported and are generating a great deal of interest. However, there is no efficient entry to asymmetric tetrazines and those with strong electron withdrawing groups, which limits the development of this field. Herein, we report a general and efficient entry to asymmetric tetrazines with strongly electron withdrawing groups.