Synthetic studies directed toward dideoxy lomaiviticinone lead to unexpected 1,2-oxazepine and isoxazole formation.
In the course of studies directed toward the synthesis of dideoxy lomaiviticinone, 3-(nitromethyl)cyclohexenones 2a (X = H) and 2b (X = I) were prepared. The corresponding enolates were reacted with naphthazarin (1) and unexpectedly afforded 1,2-oxazepine 3 and isoxazole 4, respectively. Rationale for their formation is proposed.
Department of Chemistry, Vanderbilt University, Vanderbilt Institute of Chemical Biology, Nashville, Tennessee 37235, USA.
Aleksandra
A
Baranczak
Gary A
GA
Sulikowski
D016227:Benzoquinones / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis*; D007555:Isoxazoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D010077:Oxazepines / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000138:chemical synthesis*
D016227:Benzoquinones; D003512:Cyclohexanones; D007555:Isoxazoles; D010077:Oxazepines; D011083:Polycyclic Compounds; C572035:dideoxy lomaiviticinone; C004532:quinone