Synthesis of 1-Azaspiro[4.5]deca-1,3-dienes from N-Propargylic β-Enaminones in Basic Medium

Dedicated to Prof. Dr. İlker Özkan on the occasion of his 70^th birthday

Abstract

A facile, efficient and unprecedented method for the synthesis of spiro-2H-pyrroles is reported. When reacted with 1-ethynylcyclohexylamine, α,β-alkynic ketones produced cyclohexane-embedded N-propargylic β-enaminones, which in the presence of cesium carbonate underwent nucleophilic cyclization to afford 1-azaspiro[4.5]deca-1,3-diene derivatives in good to excellent yields. This cyclization was found to be general for a variety of cyclohexane-embedded N-propargylic β-enaminones and demonstrated good tolerance to a broad range of aliphatic, aromatic and heteroaromatic groups with electron-withdrawing and electron-donating substituents. The decoration of pyrrole compounds with a spiro framework may exhibit potential for the synthesis of molecules of pharmacological interest.

Key words

pyrroles - 2H-pyrroles - N-propargylic β-enaminones - spiro compounds - nucleophilic cyclization

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