216104-72-2Relevant articles and documents
Synthesis of α-carbolines and β-carbolinones via intramolecular Diels- Alder reactions of 2(1H)-pyrazinones
Tahri, Abdellah,Buysens, Kris J.,Van Der Eycken, Erik V.,Vandenberghe, Didier M.,Hoornaert, Georges J.
, p. 13211 - 13226 (2007/10/03)
2(1H)-Pyrazinones bearing a X-(o-C6H4)-C≡C-R moiety (X=NH, NAc) are shown to undergo an intramolecular cycloaddition-elimination reaction on thermolysis in refluxing bromobenzene yielding α-carbolines or β- carbolinones. The product distribution depends strongly on the substitution pattern of the pyrazinone precursors and the solvent used for thermolysis. A high yield and selective formation of β-carbolinones is possible when heating in tetrahydronaphthalene at reflux. Use of acetic anhydride as solvent facilitated the reaction and made it possible to realise a carbolin(on)e unaccessible by thermolysis in the previously mentioned solvents.