Reaction of dimethylaminomethylenemalonaldehyde bis-N,O-acetal with ketones. A novel route to N-methylpyrroles

Article abstract of DOI:10.1007/BF01164785

Condensation of the bis-N,O-acetal of dimethylaminomethylenemalonaldehyde with ketones, β-dimethylaminovinylketones, and δ-dimethylaminodienones is accompanied by an unusual intramolecular cyclization to give cross conjugated cyclic or acylic ketones containing an N-methyl-pyrrole ring in the β- or β- and β′-positions. This is a novel route to substituted pyrroles. Treatment of the bis-N,O-acetal of dimethylaminomethylenemalonaldehyde with 2-(3′-dimethylaminopropen-2′-ylidene)cyclopentanone gave a polyenyl tris-dimethylaminodiketone. 1996 Plenum Publishing Corporation.