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 explai...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-10, Vol.74 (19), p.7315-7321
Main Authors: Malamidou-Xenikaki, Elizabeth, Spyroudis, Spyros, Tsanakopoulou, Maria, Hadjipavlou-Litina, Dimitra
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Amides - chemical synthesis
Amides - chemistry
Amines - chemistry
Azepines - chemistry
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Indenes - chemistry
Iodobenzenes - chemistry
Kinetics and mechanisms
Molecular Structure
Organic chemistry
Oxidation-Reduction
Preparations and properties
Reactivity and mechanisms
Stereoisomerism
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9013063