A highly
efficient synthetic route to new quinone–indolizine
hybrids was accomplished from quinones and N-substituted
pyrrole-2-carboxaldehydes via a domino Michael addition-aldol condensation-aromatization
sequence through which the central pyridine ring was constructed in
atom-economical and environment-friendly manner. Post modification
of the resulting products was also demonstrated, enabling further
expansion of this heterocyclic chemical space. Biological evaluation
of the quinone–indolizine hybrids revealed potent anticancer
effects in human prostate adenocarcinoma cells (PC-3) and oral adenosquamous
carcinoma cells (CAL-27).