95884-08-5

Upstream product

• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 95884-03-0 2,3,5,8-tetrahydro-6,7-bis(iodomethyl)-2-phenyl-1H-<1,2,4>-triazolo<1,2-a>pyridazine-1,3-dione 
• 80356-22-5 2,3-bis(iodomethyl)buta-1,3-diene 
• 941-69-5 N-phenyl-maleimide 
• 95884-04-1 2,3,5,6,7,8-hexahydro-6,7-dimethylene-2-phenyl-1H-<1,2,4>-triazolo<1,2-a>pyridazine-1,3-dione 

Relevant academic research and scientific papers

AZO DIENOPHILES. DIELS-ALDER REACTIONS OF 4-PHENYL-1,2,4-TRIAZOLE-3,5-DIONE AND 5-PHENYLPYRAZOL-3-ONE WITH FUNCTIONALISED DIENES

4-Phenyl-1,2,4-triazole-3,5-dione (PTAD) undergoes a Diels-Alder reaction with a variety of functionalised dienes.The adduct (9) from 2,3-bis(iodomethyl)butadiene gives, on treatment with zinc-copper couple, the diene 2,3,5,6,7,8-hexahydro-6,7-dimethylene-2-phenyl-1H-triazolo-pyridazine-1,3-dione (10) which then reacts with dienophiles in a tandem Diels-Alder reaction.The unsymmetrical azo dienophile, 5-phenylpyrazol-3-one (3), reacts regioselectively with 1-acetoxy-butadiene to give, after hydrolysis, the alcohol 5,8-dihydro-8-hydroxy-3-phenyl-1H-pyrazolo-pyridazin-1-one (19).