title: Synthesis of fused bromofurans via Mg-mediated dibromocyclopropanation of cycloalkanone-derived chalcones and Cloke-Wilson rearrangement.
abstract: A convenient two-step sequence for the conversion of alkylidenecycloalkanones to bromofurans is reported. The steps involve Mg-mediated diastereoselective dibromocyclopropanation of alkylidenecycloalkanone followed by acidic alumina-mediated regioselective ring expansion of the cyclopropyl ketone. The scope of the reaction was investigated using alkylidenecycloalkanones derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans fused to various benzocycloalkanes. Representative examples of stereoconvergent dibromocyclopropanation and total aromatization of the furobenzocycloalkane are also reported.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Bombay, Mumbai 400 076, India.
authors.forename: Elumalai
authors.initials: E
authors.lastname: Gopi
authors.forename: Irishi N N
authors.initials: IN
authors.lastname: Namboothiri
mesh_terms: D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry*; D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D047188:Chalcones; D003516:Cycloparaffins; D005663:Furans; D007659:Ketones; D008274:Magnesium