Facile regioselective synthesis of functionalized heterocycle-tethered spiro compounds via an intramolecular electrophilic Ipso - Iodocyclization process

Article abstract of DOI:10.1055/s-0031-1289526

A general, regioselective, and efficient intramolecular electrophilic ipso-iodocyclization of a series of N-alkyl-N-aryl phenylpropiolamides in the presence of I₂ (molecular iodine) and NaHCO₃ via 5-endo-dig mode of cyclization has been developed for the synthesis of hitherto unreported coumarin, quinolone, and pyrimidine-annelated heterocyclic compounds in excellent yields (84-92%). The development of this methodology provides efficient and mild reaction conditions that allow for easy isolation of products. The synthesized spiro derivatives offer an attractive and useful scope for further functionalization and to synthesize new bioactive heterocycles. Georg Thieme Verlag Stuttgart · New York.