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Environmentally friendly domino multicomponent strategy for the synthesis of pyrroloquinolinone hybrid heterocycles

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. The 1,3-dipole component was generated in situ from N-...

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Detalles Bibliográficos
Autores principales: Mani, Suresh, Raju, Rajesh, Raghunathan, Raghavacharry, Arumugam, Natarajan, Almansour, Abdulrahman I., Kumar, Raju Suresh, Perumal, Karthikeyan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9131013/
https://www.ncbi.nlm.nih.gov/pubmed/35685174
http://dx.doi.org/10.1039/d2ra02851d
Descripción
Sumario: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. The 1,3-dipole component was generated in situ from N-methylgylcine/l-proline and isatin, while the Baylis–Hillman adduct prepared from pyrene-1-carbaldehyde and various benzaldehydes is used as the dipolarophile. The domino protocol comprises 1,3-dipolar cycloaddition and a consequent double annulation reaction process. The advantages of this cascade protocol include environmentally friendly conditions, the avoidance of toxic organic solvents, simple work-up and good to excellent product yields.