Multicomponent Domino Synthesis of Highly Functionalized Aryl and Heteroaryl Fused Pyrroloquinolinone Ring Systems via Environmentally Benign Solid-state Melt Reaction

Abstract

A solid-state melt reaction has been demonstrated via a domino multicomponent process for the synthesis of highly functionalized aryl/heteroaryl fused polycyclic pyrroloquinolinone frameworks in good to excellent yields. The multicomponent domino reaction sequence involves 1,3-dipolar cycloaddition and concomitant double annulation reaction process. Baylis-Hillman adducts derived from various aryl/heteroaryl aldehyde were used as dipolarophiles, while the 1,3-dipole components were azomethine ylides generated in situ from indoline-2,3-dione and N-methylglycine/L-proline/L-pipecolinic acid. The reaction is highly regio and stereoselective, atom economic and environmentally benign in nature. The structure of compounds was elucidated through spectroscopic techniques and unambiguously ascertained by single crystal X-diffraction analysis.