Direct synthesis of N-aryl/alkyl 3-carbonylpyrroles from the Morita–Baylis–Hillman acetate of 2,2-dimethoxyacetaldehyde and a primary amine

Abstract

A kalinite catalyzed direct synthesis of N-substituted 3-carbonylpyrroles from the Morita–Baylis–Hillman acetate of 2,2-dimethoxyacetaldehyde and a primary amine in ethanol was developed.

Montmorillonite K10 catalyzed facile synthesis of N-substituted indoles from primary amines and Morita–Baylis–Hillman acetate of cyclohexenone

“…12 Recently we disclosed that the MBH acetate of acrylate and 2,2-dimethoxyacetaldehyde reacted readily with aniline under acidic conditions to afford 3-carbonylpyrrole via a tandem S N 2′ substitution–intramolecular condensation–deprotonative aromatization process. 13 When the corresponding MBH acetate of cyclohexenone was employed as a substrate, cyclohexenone fused pyrrole was proposed to be formed, which might further undergo oxidation to provide 4-hydroxyindole derivatives. However, to our surprise, a simple N -arylindole was generated (Scheme 1c).…”