Base-Mediated Self-Organization of Acetylene Gas, Nitriles, and Ketones.

An efficient approach to access diversely substituted pyridines via a three-component reaction of industrially available acetylene gas, nitriles, and ketones under basic conditions has been developed. This multimolecular self-organization is triggered by the addition of acetylenic carbanions to the C≡N bond of nitrile followed by the involvement of the ketone molecule to build up the pyridine ring. The broad range of simple substrates, one-pot operation, transition-metal-free conditions, and wide variety of synthesized pyridine-tailored heterocyclic systems make the approach of high practical value alone theoretically significant.