De Novo Synthesis of 2,2'-Bipyridines and Related Bis-azines via Cascade Coupling and Double Pyridannulation of Isocyanides.

ABSTRACT

Herein, we present a new and general protocol for the assembly of 2,2'-bipyridyls from nonpyridine substrates without using any metal catalysts or organometallic reagents. The process starts from the coupling of two 1,3-dienyl isocyanides followed by a 6π-electrocyclization/aromatization cascade featuring the simultaneous formation of two pyridine rings in a single operation. Notably, this strategy is also applicable to the construction of nonsymmetrical 2-(2-pyridyl)-quinolines/-quinoxalines. Furthermore, the aggregation-induced emission (AIE) characteristics endow our approach with great potential in biorelevant fields.