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The use of Smiles rearrangement in Ugi-type couplings with tropolone allows very straightforward multicomponent formation of 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives. The Ugi four-component reaction of isocyanides with tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one), primary amines and aldehydes proceeds smoothly and cleanly under mild conditions to afford 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives in fairly good yields.

bulletin of the korean chemical society

Four-Component Synthesis of 2-(N,N-Dialkylamino)-2,4,6-Cycloheptatrien-1-One Derivatives from Tropolone, an Isocyanide, a Primary Amine and an Aldehyde via Ugi-Smiles Coupling Reaction