Synthesis of 1-substituted benzo[c]isoxazol-3(1H)-imines via tandem nitroso-ene/intramolecular cyclizations of 2-nitrosobenzonitrile.
Instead of reacting via the expected coarctate cyclization pathway, 2-nitrosobenzonitrile undergoes a tandem nitroso-ene/intramolecular cyclization to form benzo[c]isoxazol-3(1H)-imines in very good yields under neutral conditions and at moderate temperatures. Treatment of three of the imines with HBF4 results in dimerization/condensation to furnish unusual, delocalized cationic systems.
Jeffrey
Jenna L
JL
Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA.
McClintock
Sean P
SP
Haley
Michael M
MM
D000475:Alkenes / Q000737:chemistry; D001554:Benzene / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D007555:Isoxazoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D009603:Nitroso Compounds / Q000737:chemistry*
D000475:Alkenes; D007097:Imines; D007555:Isoxazoles; D009570:Nitriles; D009603:Nitroso Compounds; C014356:benzonitrile; D001554:Benzene