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One-Pot Synthesis of Spiro-2H-pyrroles fromN-Propargylic beta-Enaminones

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2019-06-01
KARADENİZ, EDA
Zora, Metin
A simple and general one-pot method for the synthesis of spiro-2 H -pyrroles has been developed. Initially, cyclohexane-embedded -enaminones with internal alkyne functionality were synthesized by conjugate addition of 1-ethynylcyclohexylamine to ,-alkynic ketones, followed by palladium-catalyzed coupling of the resulting N -propargylic -enaminones with aryl iodides. When subjected to basic conditions, the cyclohexane-embedded -enaminones with internal alkyne functionality underwent tandem nucleophilic cyclization and benzylic C-H oxidation to furnish 3,4-diaryloyl-1-azaspiro[4.5]deca-1,3-diene derivatives in good yields.