Tetrahedron p. 14675 - 14684 (1999)
Update date:2022-08-04
Topics:
Tahri
De Borggraeve
Buysens
Van Meervelt
Compernolle
Hoornaert
2(1H)-Pyrazinones bearing an X-(o-C6H4)-C≡C-R moiety (X=O or NH; R=H, Ph or TMS) at position 3 were subjected to intramolecular Diels-Alder reaction. For the ether compounds (X=O) cycloaddition-elimination occurred readily to produce either benzofuro[2,3-c]pyridin-1(2-H)-ones or benzofuro[2,3-b]pyridines. For the aniline derivatives (X=NH, R=H or TMS) thermolysis in acetic anhydride resulted in a similar product distribution of β-carbolinones and α-carbolines which, however, differed from that obtained previously in refluxing tetrahydronaphthalene. This result is explained by the cycloaddition proceeding from the aniline NH-acetylated precursor. However, the aniline derivatives with Ph as the acetylenic end group (X=NH, R=Ph) reacted via a divergent pathway to produce N-(2-oxopyrazin-3-yl)-2-Ph- substituted indoles.
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