289-96-3

Usage

Structure

Six-membered ring with three nitrogen atoms and three carbon atoms

Aromatic compound

Yes

Stability

Highly stable

Industrial applications

a. Precursor for herbicides
b. Precursor for dyes
c. Precursor for pharmaceuticals

Use in organic synthesis

Building block

Use in chemical reactions

Reagent

Derivatives

Shown potential as anti-cancer and anti-viral agents in pharmaceutical research

Importance

Valuable chemical compound in various industries due to versatile properties and wide range of applications

InChI:InChI=1/C3H3N3/c1-2-4-6-5-3-1/h1-3H

Upstream product

• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 111729-13-6 N,N'-bis-(2,2,6,6-tetramethyl-4-piperidinyl)-formamidine 
• 109-76-2 Trimethylenediamine 
• 288-13-1 NH-pyrazole 
• 3994-46-5 N-aminopyrazole 

Downstream Products

• 533-37-9 2,3-cyclopentenopyridine 
• 123-73-9 trans-Crotonaldehyde 
• 101219-10-7 5-methyl-2,5-dihydro-1,2,3-triazine 
• 14371-10-9 (E)-3-phenylpropenal 
• 101219-11-8 5-phenyl-2,5-dihydro-1,2,3-triazine 
• 106636-96-8 5-phenyl-1,2,3-triazine 
• 539-32-2 3-butylpyridine 
• 71591-87-2 3-(aminomethylene)pentane-2,4-dione 
• 34671-83-5 2,2'-Bipyrimidine 
• 10500-57-9 5,6,7,8-tetrahydroquinoline 
• 58173-74-3 2-cyclopropyl pyrimidine 
• 210354-17-9 2-(4-bromophenyl)pyrimidine 
• 68049-17-2 2-(4-fluorophenyl)-pyrimidine 
• 69491-52-7 2-(3-nitrophenyl)pyrimidine 

Relevant academic research and scientific papers

1,2,3-Triazine

1,2,3-Triazine was obtained by nickel peroxide oxidation of N-aminopyrazole.

Access to pyridines via cascade nucleophilic addition reaction of 1,2,3-triazines with activated ketones or acetonitriles

We studied the cascade nucleophilic addition reactions of 1,2,3-triazines with activated acetonitriles or ketones, which were used to construct highly substituted pyridines that are not easily accessed by conventional methods. The strategy addressed some structural diversity issues currently facing medicinal chemistry, and the resulting pyridines could be used as convenient precursors for the synthesis of related pharmaceuticals. In particular, our method was applied to the syntheses of the marketed drug etoricoxib and several biologically important molecules in a few steps.

Scope of the inverse electron demand Diels-Alder reactions of 1,2,3-triazine

Chemical equations presented. An examination of the scope of the inverse electron demand Diels-Alder reactions of the parent unsubstituted 1,2,3-triazine is described including the first report of its unique capabilities for participating in previously unexplored [4 + 2] cycloaddition reactions with heterodienophiles.

Inverse electron demand diels-alder reactions of 1,2,3-triazines: Pronounced substituent effects on reactivity and cycloaddition scope

A systematic study of the inverse electron demand Diels-Alder reactions of 1,2,3-triazines is disclosed, including an examination of the impact of a C5 substituent. Such substituents were found to exhibit a remarkable impact on the cycloaddition reactivity of the 1,2,3-triazine without altering, and perhaps even enhancing, the intrinsic cycloaddition regioselectivity. The study revealed not only that the reactivity may be predictably modulated by a C5 substituent (R = CO2Me > Ph > H) but also that the impact is of a magnitude to convert 1,2,3-triazine (1) and its modest cycloaddition scope into a heterocyclic azadiene system with a reaction scope that portends extensive synthetic utility, expanding the range of participating dienophiles. Significantly, the studies define a now powerful additional heterocyclic azadiene, complementary to the isomeric 1,2,4-triazines and 1,3,5-triazines, capable of dependable participation in inverse electron demand Diels-Alder reactions, extending the number of complementary heterocyclic ring systems accessible with implementation of the methodology.

Trisubstituted heterocyclic compounds and their use as fungicides

Compounds of general formula (I): in which:Het represents a five or six membered saturated, partially unsaturated or aromatic ring containing between one and six heteroatoms of the group N, O, S, in which the heterocycle is substituted in an adjacent manner with -P-Q1-T-Q2, -GZ and Y, such that the substituant -GZ is adjacent to both. the other substituants being as defined in the description,process for preparing these compounds,fungicidal compositions comprising these compounds,processes for treating plants by applying these compounds or compositions.

Polytriazine compounds containing recurring piperidylamidinotriazine structural units and their use as stabilizers for organic materials

Polytriazine compounds having a number average molecular weight from 1000 to 20,000 and containing recurring piperidylamidinotriazine structural units of the formula (IA) STR1 or a combination of said structural units of the formula (IA) with recurring structural units of the formula (IB) with molar proportions of (IA) and (IB) from 30% to 100% for (IA) and 0 to 70% for (IB), wherein A is a group of the formula (II) STR2 and L1, L2, L3, R1 and R2 are as defined in claim 1, can be used as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.

Reactions of N-Aminopyrazoles with Halogenating Reagents and Synthesis of 1,2,3-Triazines

Reactions of N-aminopyrazoles with halogenating reagents (Cl2, Br2, I2, BrCl, ICl, IBr, N-chlorosuccinimide, and N-bromosuccinimide) were examined.Some of these reagents preferentially lead to oxidation of the amino group to give the corresponding 1,2,3-triazines as major products, while others mainly gave either or both of 1-amino-4-halopyrazoles and 5-halo-1,2,3-triazines as the result of halogenation of the 4-position of the pyrazole ring prior to the oxidation of the amino group.In some cases, the oxidation of the amino group and the halogenation of the pyrazole ring proceeded concurrently to form not only the unhalogenated triazines but also the 1-amino-4-halopyrazoles and the 5-halotriazines.Various reagents and reaction conditions were explored to utilize the reaction for the synthesis of halogenated and unhalogenated 1,2,3-triazines.Keywords - 1,2,3-triazine; halo-1,2,3-triazine; pyrazole; 1-aminopyrazole; 1-aminohalopyrazole; synthesis; oxidation; halogenation; ring expansion

1,2,3-Triazines,III. - Synthesis of N-Aminopyrazoles and their Oxidation to 1,2,3-Triazines. Molecular Structure of 1,2,3-Triazine

Oxidation of the N-aminopyrazoles 4a-i affords the 1,2,3-triazines 5a-i.Spectra and reactions - such as oxidation, reduction, and cycloaddition reactions - of some 1,2,3-triazines 5 are described.The X-ray analysis of 5a is presented.

Oxidation of 1-Aminopyrazoles and Synthesis of 1,2,3-Triazines

Unsubstituted and various substituted monocyclic 1,2,3-triazines were synthesized from 1-aminopyrazoles by oxidation with lead tetraacetate, lead dioxide-CF3CO2H, and/or nickel peroxide-AcOH.