Azabenzocycloheptenones. Part XV. Synthesis of benzazatropones and a quinoline aldehyde by the dehydrogenation of certain tetrahydro-1-benzazepine derivatives
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2012-2017
- https://doi.org/10.1039/p19720002012
Abstract
4,4,7,9-Tetrabromo-1,2,3,4-tetrahydro-1-benzazepin-5-one (IV) reacts with lithium chloride in dimethylformamide to give 6,8-dibromoquinoline-4-carbaldehyde (VII) and with active manganese dioxide to give 4,7,9-tribromo-1-benzazepin-5-one (I; R1= R4= H, R2= R3= R5= Br) and 4,7,9-tribromo-1-benzazepine-2,5-dione (VI; R1= Br, R2= H). The latter has been converted into 4,7,9-tribromo-2-chloro-1-benzazepin-5-one (I; R1= Cl, R4= H, R2= R3= R5= Br). 1,2,3,4-Tetrahydro-2-methyl-1-p-tolylsulphonyl-1-benzazepin-5-one (XIII; R = tosyl), the N-acetyl derivative (XIII; R = Ac) and several related compounds are reported. Treatment of ethyl γ-[N-(o-methoxycarbonylphenyl)acetamido]butyrate (XVI; R1= Ac, R2= H) with potassium t-butoxide gave ethyl γ-(1,2-dihydro-4-hydroxy-2-oxoquinolin-1-yl)butyrate (XVII).Keywords
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