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Synthesis of 2-alkoxy(aroxy)-3-substituted quinolines by DABCO-promoted cyclization of o-alkynylaryl isocyanides.

Diversified 2-alkoxy- and 2-aroxy-3-substituted quinolines were synthesized from o-alkynylaryl isocyanides and alcohols and phenols promoted by DABCO, respectively. The reaction was initiated by nucleophilic addition of DABCO to isocyanide and subsequent cycliztion, leading to a DABCO-quinoline-based adduct as the reactive intermediate, followed by substitution of the DABCO moiety with oxygenated nucleophiles.