A domino reaction for the synthesis of 2H-pyrano-[4aEuro(3),3aEuro(3),2aEuro(3):4',5']chromeno[2',3':4,5]thieno-[2,3-b]pyridin-2-ones

摘要

2-{[(5-Hydroxy-2-oxo-2H-chromen-4-yl)methyl]sulfanyl}pyridine-3-carbonitrile derivatives were synthesized in a reaction of 4-chloromethyl-5-hydroxycoumarin with substituted 2-thioxopyridine-3-carbonitriles. The presence in the molecule of spatially adjacent active methylene, nitrile, and hydroxyl groups under the action of a base leads to consecutive intramolecular cyclization reactions with the formation of a novel heterocyclic system pyrano[4aEuro(3),3aEuro(3),2aEuro(3):4',5']chromeno[2',3':4,5]thieno[2,3-b]pyridine.