Synthesis of Tetrazolo[5,1-a]isoquinolines via a Suzuki-Miyaura Coupling Reaction/[3 + 2] Cycloaddition Sequence.

ABSTRACT

An efficient copper-catalyzed method for the synthesis of tetrazolo[5,1-a]isoquinolines has been developed starting from alkenyl-1,2-bis(boronates). The domino reaction underwent a Suzuki-Miyaura cross-coupling reaction and an azidation followed by an in situ [3 + 2] cycloaddition. Regioselective synthesis has been demonstrated by inverting the Suzuki-Miyaura cross-coupling reaction and the azidation.