97130-12-6

Upstream product

• 97130-11-5 5,5-dimethyl-3,6-diphenyl-6-pyrrolidino-5,6-dihydro-2-pyranone 
• 63617-45-8 2,5-diphenyl-6H-1,3,4-oxadiazin-6-one 
• 2403-57-8 1-(2-methylprop-1-en-1-yl)pyrrolidine 

Downstream Products

• 97130-13-7 6-Hydroxy-5,5-dimethyl-3,6-diphenyl-5,6-dihydro-pyran-2-one 
• 97130-14-8 methyl Z-4,4-dimethyl-2,5-diphenyl-5-oxo-2-pentenoate 

Relevant academic research and scientific papers

Diels-alder cycloadditions of 1,3,4,-oxadiazin-6-ones with electron rich pi systems

A study of the cycloaddition behavior of several 2,5-disubstituted 1,3,4-oxadiazin-6-ones with electron rich pi bonds has been carried out. trans-1-Propenylpyrrolidine was found to react with the oxadiazinone ring system to give rise to a ring opened diazatrienyl substituted carboxylic acid. Further heating of the acid results in decarboxylation, hydrolysis, cyclization and pyrrolidine elimination to produce a disubstituted pyrazole. Reaction with the trisubstituted enamine 1 - ( 2 - methyl-propenyl) pyrrolidine, was also studied in some detail. The cycloadditions encountered can be rationalized as proceeding by an initial Diels-Alder reaction followed by cheletropic extrusion of nitrogen to produce a ketoketene intermediate. The fate of the ketene is markedly dependent upon the overall pattern of substitution. Some of the products formed can be explained in terms of a competitive migration of the pyrrolidino group to the ketene and benzoyl groups. With one system the major cycloadduct is derived from the Diels-Alder reaction of a transient azaketene tautomer formed by an electrocyclic opening of the oxadiazinone ring.