An efficient and elegant assembly of pyrene/aryl fused pyrrolo[2,3-b]quinolinone and pyrrolizino[3,2-b]quinolinone hybrid heterocycles was achieved via a domino multicomponent reaction strategy using a solid state melt reaction (SSMR) condition.
Structurally diverse fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrids were synthesized to get excellent yields via a tandem multi-component reaction sequence employing an environmentally benign solid state melt reaction involving [3+2]-cycloaddition process followed by two consecutive annulation steps. Baylis–Hillman products, used as dipolarophiles, were synthesized from various substituted aryl/heteroaryl aldehydes in the presence of DABCO and methyl acrylate, while the 1,3-dipole component was derived in situ from indoline-2,3-dione and acyclic/cyclic amino acid viz N-methylgylcine/l-proline. The structure of the unusual tandem products was unambiguously assigned by spectroscopic and XRD analysis. The products arose through the formation of three new rings, five new bonds, and three adjoining stereocenters with complete diastereomeric control.
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.
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