Hetero-Tetradehydro-Diels–Alder Cycloaddition of Enynamides and Cyanamides: Gold-Catalyzed Generation of Diversely Substituted 2,6-Diaminopyridines
Nikolay V. Shcherbakov, Dmitry Dar’in, Vadim Yu. Kukushkin, Alexey Yu. Dubovtsev
Abstract
Gold(I)-catalyzed hetero-tetradehydro-Diels–Alder cycloaddition of enynamides and cyanamides comprises an efficient route to diversely substituted 2,6-diaminopyridines (28 examples; yields up to 99%). The reaction proceeds under very mild conditions (DCM, rt) with high functional group tolerance. The obtained 2,6-diaminopyridines represent a useful synthetic platform with an easily modulated substitution pattern for subsequent functionalizations of both the pyridine core and the N-substituents.
Topics & Concepts
CycloadditionCatalysisPyridineChemistryDiels–Alder reactionCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalytic Alkyne ReactionsSynthetic Organic Chemistry MethodsCatalytic C–H Functionalization Methods