69466-83-7

Usage

InChI:InChI=1/C11H11N3OS/c1-15-9-5-3-8(4-6-9)10-7-12-14-11(13-10)16-2/h3-7H,1-2H3

Upstream product

• 35600-34-1 S-methylisothiosemicarbazide hydroiodide 
• 1076-95-5 p-methoxyphenylglyoxal 
• 44387-06-6 methyl hydrazinecarbimidothioate 
• 1672-34-0 3,6-dimethylthio-1,2,4,5-tetrazine 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 832686-53-0 2,5-dihydro-5-(p-methoxyphenyl)-3-methylsulfanyl-1,2,4-triazine 

Downstream Products

• 69466-85-9 3-Methoxy-5-(4'-methoxyphenyl)-1,2,4-triazin 
• 114954-25-5 5-(4'-methoxyphenyl)-3-(methylsulfonyl)-1,2,4-triazine 
• 114954-35-7 2-(4'-methoxyphenyl)benzfuro<2,3-b>pyrazine 
• 114954-30-2 3-(2'-cyanophenoxy)-5-(4'-methoxyphenyl)-1,2,4-triazine 
• 1234382-57-0 5-(4-methoxyphenyl)-N-(4-trifluoromethylphenyl)-1,2,4-triazin-3-amine 
• 1234382-62-7 5-(4-methoxyphenyl)-N-(4-benzyloxyphenyl)-1,2,4-triazin-3-amine 
• 1234382-55-8 5-(4-methoxyphenyl)-N-(3,5-difluorophenyl)-1,2,4-triazin-3-amine 
• 1234382-48-9 5-(4-methoxyphenyl)-N-(3-methoxyphenyl)-1,2,4-triazin-3-amine 
• 1234382-50-3 5-(4-methoxyphenyl)-N-(4-tolyl)-1,2,4-triazin-3-amine 
• 1234382-53-6 5-(4-methoxyphenyl)-N-(4-chlorophenyl)-1,2,4-triazin-3-amine 
• 1234382-45-6 5-(4-methoxyphenyl)-N-(4-methoxyphenyl)-1,2,4-triazin-3-amine 
• 1234382-52-5 5-(4-methoxyphenyl)-N-phenyl-1,2,4-triazin-3-amine 

Relevant academic research and scientific papers

Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding

An unprecedented 1,4-cycloaddition (vs 3,6-cycloaddition) of 1,2,4,5-tetrazines is described with preformed or in situ generated aryl-conjugated enamines promoted by the solvent hydrogen bonding of hexafluoroisopropanol (HFIP) that is conducted under mild reaction conditions (0.1 M HFIP, 25 °C, 12 h). The reaction constitutes a formal [4 + 2] cycloaddition across the two nitrogen atoms (N1/N4) of the 1,2,4,5-tetrazine followed by a formal retro [4 + 2] cycloaddition loss of a nitrile and aromatization to generate a 1,2,4-triazine derivative. The factors that impact the remarkable change in the reaction mode, optimization of reaction parameters, the scope and simplification of its implementation through in situ enamine generation from aldehydes and ketones, the reaction scope for 3,6-bis(thiomethyl)-1,2,4,5-tetrazine, a survey of participating 1,2,4,5-tetrazines, and key mechanistic insights into this reaction are detailed. Given its simplicity and breath, the study establishes a novel method for the simple and efficient one-step synthesis of 1,2,4-triazines under mild conditions from readily accessible starting materials. Whereas alternative protic solvents (e.g., MeOH vs HFIP) provide products of the conventional 3,6-cycoladdition, the enhanced hydrogen bonding capability of HFIP uniquely results in promotion of the unprecedented formal 1,4-cycloaddition. As such, the studies represent an example of not just an enhancement in the rate or efficiency of a heterocyclic azadiene cycloaddition by hydrogen bonding catalysis but also the first to alter the mode (N1/N4 vs C3/C6) of cycloaddition.

New heteroaromatic aminations on 5-aryl-1,2,4-triazines and 1,2,4,5-tetrazines by palladium catalysis

The efficient and original palladium-catalyzed amination of 5-Aryl-1,2,4-triazines and 1,2,4,5-tetrazines is reported. This Buchwald-Hartwig type reaction leads to the formation of aminated heterocycles via methylsulfur release. The reaction is optimized and a wide range of amines is used to determine the scope and limitations of this methodology.

A general approach to selective functionalization of 1,2,4-triazines using organometallics in palladium-catalyzed cross-coupling and addition reactions

A selective way to obtain disubstituted 1,2,4-triazines in good yields by combining addition reactions and palladium-catalyzed cross-coupling reactions of organometallics with 3-methylsulfanyl-1,2,4-triazine is described.

HETERODIENOPHILIC INTRAMOLECULAR DIELS-ALDER REACTIONS OF 1,2,4-TRIAZINES. SYNTHESIS OF NOVEL POLYCYCLIC CONDENSED PYRAZINES AND LUMAZINES

3-(2'-Cyanophenoxy)-1,2,4-triazines and 7-(2'-cyanophenoxy)-6-azalumazines undergo intramolecular Diels-Aledr reactions to yield novel polycyclic pyrazines and lumazines.However, the analogous 5-(2'-cyanophenoxy)-1,2,4-triazines fail to undergo cycloaddit

Pharmacologically active substituted 1,2,4-triazines

Substituted 1,2,4-triazines, compositions thereof and methods of using same are described. The compounds of the invention exhibit a wide range of pharmacological activity including anti-inflammatory, analgesic, anti-pyretic, hypotensive and central nervous system effects.