448957-76-4

Upstream product

• 62-53-3 aniline 
• 525-06-4 diphenyl ketene 
• 126404-75-9 N-((1E,4E)-1,5-diphenylpenta-1,4-dien-3-ylidene)aniline 
• 35225-79-7 dibenzylideneacetone 
• 448957-69-5 1,3,3-Triphenyl-4,4-bis-((E)-styryl)-azetidin-2-one 

Relevant academic research and scientific papers

Diene-transmissive hetero Diels-Alder reaction of cross-conjugated azatrienes with ketenes: A novel and efficient, stereo-controlled synthetic method for hexahydroquinolinones

The cross-conjugated azatrienes, N-aryl-, N-alkyl- or N-dimethylamino-diβ-styrylmethanimines, reacted with diphenylketene and dimethylketene at room temperature to afford [2+2] cycloadducts, while the reaction with dichloroketene produced [4+2] cycloadducts. Upon heating, the [2+2] cycloadducts underwent a [1,3] sigmatropic rearrangement giving the formal [4+2] cycloadducts. The second Diels-Alder reaction of the [4+2] mono-adducts with electron-deficient dienophiles such as tetracyanoethylene, N-phenylmaleimide and methyl vinyl ketone gave hexahydroquinolinone derivatives stereoselectively. The cross-conjugated azatriene bearing different substituents at β- and β′-positions also underwent the diene-transmissive hetero Diels-Alder reaction in a highly site-, regio- and stereo-selective manner.