Catalysis Science and Technology.
Royal Society of Chemistry.
Vol. 8.
2018.
P. 3073-3080
A simple one-pot method for the synthesis of isomeric pyrrolo[1,2-x][1,4]diazepinones in reasonable yields was developed. The method is based on the condensation of readily available N-Boc amino acids with biomass-derived furans containing aminoalkyl groups followed by deprotection, furan ring opening, and Paal-Knorr cyclization. Using this approach, we synthesized pyrrolo[1,2-a][1,4]diazepin-3(2H)-ones from furfurylamines and β-amino acids and pyrrolo[1,2-d][1,4]diazepin-4(5H)-ones from 2-(2-furyl)ethylamines and α-amino acids. The cytotoxicity of the synthesized pyrrolodiazepinones was studied. © 2018 American Chemical Society.