66409-59-4

Upstream product

• 60769-85-9 rel-(1S,5R,7R)-5-ethoxycarbonyl-1,7-diphenyl-2-azabicyclo<3.2.0>heptane-3,4-dione 
• 100-42-5 styrene 
• 59046-34-3 3-ethoxycarbonyl-2-phenyldioxopyrroline 
• 60769-85-9 rel-(1S,5R,7S)-5-ethoxycarbonyl-1,7-diphenyl-2-azabicyclo<3.2.0>heptane-2,4-dione 
• 77800-62-5 dl-(1R*,5S*,7R*)-3-ethoxy-5-ethoxycarbonyl-1,7-diphenyl-2-azabicyclo<3.2.0>hept-2-en-4-one 
• 77800-62-5 dl-(1R*,5S*,7S*)-3-ethoxy-5-ethoxycarbonyl-1,7-diphenyl-2-azabicyclo<3.2.0>hept-2-en-4-one 

Downstream Products

• 66409-54-9 5-Ethoxycarbonyl-3,6-diphenyl-2-pyridone 
• 66409-56-1 5-Ethoxycarbonnyl-1-methyl-3,6-diphenyl-2-pyridone 

Relevant academic research and scientific papers

Dioxopyrrolines. XXXVI. Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Acyclic Olefins. Structural and Stereochemical Assigment of the Photocycloadducts

The photocycloaddition of the dioxopyrroline 1 to olefins with electron donating substituents proceeded with regio- and stereo-selectivity to give the 7-substituted 2-azabicycloheptane-3,4-diones 2 and 3, together with, in a few instances, the dihydropyridone 4.The stereochemistries of the adducts were dependent on the nature of the olefins.Olefins carrying phenyl, vinyl, and alkyl substituents afforded the exo-adducts 2, while olefins carrying an O-substituent afforded the endo-adducts 3, predominantly.The structures of these cycloadducts were established by X-ray crystallographic analyses, chemical correlations, and spectroscopic means.Keywords-photocycloaddition; 1H-pyrrole-2,3-dione; dioxopyrroline; 2-azabicyclo-heptane-3,4-dione; electron rich olefin; stereochemistry; cycloadduct; X-ray analysis

2-AZABICYCLOHEPTANE-3,4-DIONES (2): STEREOCHEMISTRY OF THE PHOTO-CYCLOADDUCTS OF 3-ETHOXYCARBONYL-2-PHENYL-Δ2-PYRROLINE-4,5-DIONE WITH SUBSTITUTED OLEFINS.

The stereochemistries of photo-cycloadducts of 3-ethoxycarbonyl-2-phenyl-Δ2-pyrroline-4,5-dione with substituted olefins were established by chemical and spectroscopic means.Styrene- and butadiene-major adducts were 7-exo-isomers, while ethyl vinyl ether- and vinyl acetate-major adducts were 7-endo-isomers.The 7,7'-disubstitutsd derivative, the isopropenyl acetate-adduct, was also established as an O-endo-isomer.

2-Azabicycloheptane-3,4-diones (4): thermal rearrangement of 3-ethoxy-2-azabicyclohept-2-en-4-ones leading to 2-ethoxy-3,4-dihydropyridines

Thermolysis of 3-ethoxy-2-azabicyclohept-2-en-4-ones yielded 2-ethoxy-3,4-dihydropyridines, which is explained by sigmatropic rearrangement followed by cheletropic elimination of CO

2-AZABICYCLOHEPTANE-3,4-DIONES (1). A NOVEL EPIMERIZATION REACTION OF C7-SUBSTITUENTS.

On treatment with bases, 7,7-disubstituted and 7-substituted 2-azabicycloheptane-3,4-diones rapidly epimerized at C7 to give a thermodynamically more stable isomer (7-endo isomer in the cases of monosubstituted compounds) predominantly,