223647-73-2

Upstream product

• 5292-53-5 diethyl benzalmalonate 
• 68-12-2 N,N-dimethyl-formamide 
• 61-82-5 4H-1,2,4-triazol-3-amine 
• 61-82-5 3⁽⁵⁾-amino-1,2,4-triazole 
• 103-26-4 methyl cinnamate 
• 61-82-5 3-amino-1,2,4-triazole 
• 1214-54-6 5-benzylidene Meldrum's acid 
• 103-26-4 Methyl cinnamate 

Downstream Products

• 1312928-30-5 4-hexyl-7-phenyl-6,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one 
• 1312928-29-2 4-methyl-7-phenyl-6,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one 
• 1312928-31-6 4-benzyl-7-phenyl-6,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one 
• 352279-95-9 3-(5-amino-1,2,4-triazol-1-yl)-3-phenylpropionic acid hydrazide 

Relevant academic research and scientific papers

Reactions of α-aminoazoles with diethyl benzylidenemalonate

Cyclocondensations of diethyl benzylidenemalonate with 3-amino-5- methylpyrazole, 3,5-diamino-1,2,4-triazole, 3,4,5-triamino-1,2,4-triazole, and 2-amino-benzimidazole in alcohols take a single route and lead to the formation of functionally substituted partially hydrogenated pyrazolo-, triazolo[1,5-a]-pyrimidin-5-ones and pyrimido[1,2-a]benzimidazol-2-one respectively. From reaction mixtures involving 3-amino-1,2,4-triazole and its 5-methylsulfanyl analog in methanol the intermediate products of heterocyclization were isolated forming as a result of alkylation with the β-carbon of the unsaturated ester the endocyclic nucleophilic sites of aminoazoles. The structure of one among the products obtained, diethyl(3-amino-5-methylsulfanyl-1,2,4-triazol-2-yl)benzylmalonate was proved by X-ray crystallography. In DMF the same reagents yielded mixtures of partially hydrogenated triazolo[1,5-a]pyrimidin-5-ones.

Cyclocondensation of 3-amino-1,2,4-triazole with substituted methyl cinnamates

The reaction of 3-amino-1,2,4-triazole (1) with substituted methyl cinnamates 2a-h leads selectively to the formation of 7-aryl-6,7- dihydro[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-ones 3a-h. The structure elucidation of the products is based on it, 1H and 13C mr measurements and X-ray diffraction.

Synthesis and anticonvulsant activity of 7-phenyl-6,7-dihydro-[1,2,4] triazolo[1,5-a]pyrimidin-5(4H)-ones and their derivatives

Herein, we described the syntheses and anticonvulsant activities of 7-(substituted-phenyl)-6,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-ones (1a-1o) and their derivatives. Most of the synthesized compounds exhibited potent anticonvulsant activities in the maximal electroshock test (MES). The most promising compound 1i showed significant anticonvulsant activity in MES test with ED50 value of 19.7 mg/kg. It displayed a wide margin of safety with protective index much higher than the standard drugs. In addition, the potence of compound 1i against seizures induced by Pentylenetetrazole, Isoniazid, Thiosemicarbazide, 3-Mercaptopropionic acid, and Bicuculline in the chemical-induced seizure tests suggested that compound 1i displayed broad spectrum activity in several models, and it is likely to have several mechanisms of action including inhibiting voltage-gated ion channels and modulating GABAergic activity.

Cyclocondensation of 3-amino-1,2,4-triazoles with esters of substituted cinnamic acids and aromatic unsaturated ketones

We have studied the reactions of 3-amino, 3,5-diamino-, and 3-amino-5-trifluoromethyl-1,2,4-triazole with esters of substituted cinnamic acids and aromatic unsaturated ketones; we have established the directionality of formation of the tetrahydrooxopyrimi

Reaction of arylidene derivatives of Meldrum's acid with 3-amino-1,2,4-triazole

The condensation of arylidene derivatives of Meldrum's acid with 3-amino-1,2,4-triazole in nitrobenzene leads to 4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidin-5-ones. In DMF the reaction proceeds with the formation of arylsubstituted N-(2H-1,2,4-triazol-3-yl)-3-(2H-1,2,4-triazol-3-ylamino)propionamides. 1999 KluwerAcademic/Plenum Publishers.