Synthesis, reactions, and nuclear magnetic resonance spectroscopy of 4-methyl-6H-pyrazolo(3,4-b)azepin-7-ones
作者:
Suresh Chandra Sharma,
Brian Maurice Lynch,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1979)
卷期:
Volume 57,
issue 23
页码: 3034-3040
ISSN:0008-4042
年代: 1979
DOI:10.1139/v79-494
出版商: NRC Research Press
数据来源: NRC
摘要:
Reactions of various 5-aminopyrazoles with ethyl levulinate in acetic acid have been shown to furnish moderate to good yields of the correspondingly substituted 4-methyl-6H-pyrazolo-(3,4-b)azepin-7-ones, accompanied by the acetamidopyrazoles. The courses of methylation and of bromination reactions of some of the pyrazoloazepinones have been explored and defined, and conversion of one pyrazoloazepinone into 7-chloropyrazoloazepine and thence by nucleophilic displacements into 7-(substituted amino)pyrazoloazepines has been effected. Structural assignments, tautomeric preferences, and through-space interactions between substituents were established through nuclear magnetic resonance spectroscopy (1H and13C). Some members of the pyrazoloazepinone series exhibit significant anti-inflammatory and analgesic effects in mice.
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