A convenient approach to fused indeno-1,4-diazepinones through hypervalent iodine chemistry.
Indenocarboxamides, resulting from the sequential addition of two arylamine equivalents to indanedione ketene dimer, are oxidized by [bis(trifluoroacetoxy)iodobenzene] to fused indeno-1,4-diazepinones in yields depending on the substituents on both aromatic rings. A plausible reaction pathway explaining the formation of the title compounds, as well as the formation of the two other minor products of the reaction, through a common intermediate, is suggested.
Malamidou-Xenikaki
Elizabeth
E
Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece. malamido@chem.auth.gr
Spyroudis
Spyros
S
Tsanakopoulou
Maria
M
Hadjipavlou-Litina
Dimitra
D
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001381:Azepines / Q000737:chemistry*; D003500:Cyclization; D007192:Indenes / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000577:Amides; D000588:Amines; D001381:Azepines; D007192:Indenes; D007462:Iodobenzenes; C545370:indeno-1,4-diazepinone