Cu(I)-Catalyzed Ligand-Free Tandem One-Pot or Sequential Annulation via Knoevenagel Intermediates: An Entry into Multifunctional Naphthalenes, Phenanthrenes, Quinolines, and Benzo[ b]carbazoles

Abstract

A simple but efficient one-pot or sequential copper-catalyzed protocol using 2-bromoaldehydes and active methylene group containing substrates that affords multifunctional naphthalenes, phenanthrenes, quinolines, and benzo[b]carbazoles via Knoevenagel condensation, C-arylation, and decarboxylation, followed by aromatization, is developed. The reaction utilizes the potential of Knoevenagel intermediates and does not require any ancillary ligand. The phenanthrene products thus obtained show moderate fluorescence activity. Structural elaboration of the products to obtain dihydrobenzoquinazolines is also highlighted.