Pyrroles from 3-Alkoxyacroleins and CH-acidic α-Aminoacetic Acid Derivatives

Article abstract of DOI:10.1055/s-1989-27249

2-Alkoxycarbonylpyrroles and 2-cyanopyrroles 4 are prepared in a one-step synthesis by vinylogous amidation of 3-alkoxyacroleins 1 with glycine esters 2a-c and aminoacetonitrile (2d), followed by base-catalyzed cyclodehydration of the intermediate 3-aminoacroleins 3.The 3-hydroxypropyl function can be introduced into the pyrrole ring by using 3,4-dihydro-2H-pyran-5-carbaldehyde (5) as a cyclic 3-alkoxyacrolein.