Tetrahedron p. 13211 - 13226 (1998)
Update date:2022-08-05
Topics:
Tahri, Abdellah
Buysens, Kris J.
Van Der Eycken, Erik V.
Vandenberghe, Didier M.
Hoornaert, Georges J.
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.
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