Synthesis of 2,3-Dimethoxy-7-methyl-7,12-dihydro-6H-[1]-benzofuro-[2,3-c]-[1]-benzazepin-6,12-dione

Treatment of 5,6-dimethoxy-2-(methylphenylcarbamoyl)-benzofuran-3-carboxylic acid with PPA yielded 2,3-dimethoxy-7-methyl-7,12-dihydro-6H-[1]-benzofuro-[2,3-c]-[1]-benzazepin-6,12-dione. The analogous 2-[(5,6-dimethoxybenzofuran-2-carbonyl)methylamino]benzoic acid was resistant to cyclization, where...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2002-03, Vol.7 (3), p.353-362
Main Authors: Jackson, Yvette A., Marriott, Karla-Sue C.
Format: Article
Language:English
Subjects:
12-dione
3-c] > benzazepin-6
Acids
benzofuro-
benzoxazinone
cyclization
Oxidation
PPA
Reagents
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Summary:Treatment of 5,6-dimethoxy-2-(methylphenylcarbamoyl)-benzofuran-3-carboxylic acid with PPA yielded 2,3-dimethoxy-7-methyl-7,12-dihydro-6H-[1]-benzofuro-[2,3-c]-[1]-benzazepin-6,12-dione. The analogous 2-[(5,6-dimethoxybenzofuran-2-carbonyl)methylamino]benzoic acid was resistant to cyclization, whereas 2-[(6-methoxybenzofuran-2-carbonyl)-amino]benzoic acid underwent cyclization to the corresponding 3,1-benzoxazin-4-one.
ISSN:1420-3049
1420-3049
DOI:10.3390/70300353