643755-01-5

Upstream product

• 496867-75-5 5-amino-3-(benzylsulfanyl)-N-butyl-1H-[1,2,4]triazole-1-carboxamide 
• 100-39-0 benzyl bromide 
• 3922-47-2 5-(benzylsulfanyl)-1H-[1,2,4]-triazol-3-amine 
• 643754-98-7 2-(benzylsulfanyl)-6-butyl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-one 

Downstream Products

• 1974-80-7 4-(N-butylaminocarbonyl)-morpholine 
• 1461-78-5 N-butylpyrrolidine-1-carboxamide 

Relevant academic research and scientific papers

Synthesis of triazolo[1,5-a]triazin-7-one derivatives and highly functionalized [1,2,4]triazoles

The synthesis of novel triazolo[1,5-a]triazin-7-ones is presented. Starting from 3-amino-5-sulfanyl-1,2,4-triazole, the synthetic sequence involved alkylation with benzyl bromide, reaction with p-nitrophenyl chloroformate followed by treatment with a primary amine, and condensation with diethoxymethyl acetate. Final oxidation of the thioether moiety with 3-chloroperbenzoic acid provided 2-(benzylsulfonyl)[1,2,4]tri-azolo[1,5-a][1,3,5]triazin-7-ones 5a and 5b in good overall yields. Treatment of 5a and 5b with secondary amines provided highly functionalized [1,2,4]triazoles through an unexpected triazinone ring opening. A mechanism for this transformation is proposed.