One pot synthesis of fused [1,2-a]pyrrole from 1,6-dioxo-2,4-diene and haloalkyl primary amine

The one pot synthesis of fused 2,3-dihydropyrrolizine and 6,7-dihydro-5H-indolizine involving the intermolecular dehydrative condensation of 1-phenyl-1,6-dioxo-hepta-2,4-diene with 2-chloroethylamine and 3-chloropropylamine followed by the intramolecular cyclization of the intermediary products 2-(1-chloroalkyl-5-methylpyrrol-2-yl)-1-phenylethanones in the presence of a base such as Na2CO3 and NaHCO3 is described. These also led to the concurrent formation of the oxidatively dimerized product 2,3-bis-[1,5-(2-chloroalkyl)-1-H-pyrrol-2-yl]-1,4-diphenylbutane-1,4-dione whereby the structure was further confirmed by X-ray analysis.