175468-52-7Relevant academic research and scientific papers
Sulfolene pyridinones as precursors for pyridinone ortho-quinodimethanes and their Diels-Alder adducts
Govaerts, Tom C,Vogels, Ilse,Compernolle, Frans,Hoornaert, Georges
, p. 799 - 802 (2007/10/03)
2(1H)-Pyrazinones were converted into [3,4-b] and [3,4-c] sulfolene pyridinones 4 and 5, serving as precursors for the corresponding 3,4- and 5,6-dimethylene 2(1H)-pyridinone ortho-quinodimethanes. These were trapped by in situ reaction with dienophiles. Tethering of 4 also enabled intramolecular cycloaddition.
Synthesis of new pyrrolo[3,4-b]- and [3,4-c]pyridin(on)es and related 1,7-naphthyridinones and 2,7-naphthyridines via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones
Buysens, Kris J.,Vandenberghe, Didier M.,Hoornaert, Georges J.
, p. 9161 - 9178 (2007/10/03)
2(1H)-pyrazinones 7, 10 or 12 with in 6-position a 2-propynylaminomethyl or 3-butynylaminomethyl side chain undergo intramolecular Diels-Alder reactions providing cycloadducts which can be isolated or functionalised in some cases. By further thermolysis of these compounds either pyrrolo-[3,4-b]pyridinones 15/16 and/or pyrrolo[3,4-c]pyridines 17/18 or 1,7-naphthyridinones 25 and/or 2,7-naphthyridines 26 can be generated. Loss of either cyanide or isocyanate from the respective adducts is shown to be dependent on their substitution pattern.
