Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Diazepines. XIX. Photochemical Synthesis of 2, 3-Benzodiazepines from Isoquinoline N-Imides
JYOJI KURITAMICHIKO ENKAKUTAKASHI TSUCHIYA
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1982 Volume 30 Issue 10 Pages 3764-3769

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Abstract
The photolysis of the isoquinoline N-imides (12a-g) under basic conditions gave the corresponding 5H-2, 3-benzodiazepines (13), presumably via the 1H-2, 3-benzodiazepines (17), together with the parent isoquinolines (14), whereas irradiation of these N-imides (12) under neutral conditions gave no diazepines. Treatment of the 1-methyl-5H-diazepines (13b, f) with acetic anhydride gave the 3-acetyl-3H-2, 3-benzodiazepines (18), which reverted back to the 5H-diazepines (13) on hydrolysis. However, the 1-unsubstituted 5H-diazepines showed no such conversion. Some reactions of the 5H-diazepines (13) thus obtained were also examined.
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