Synthesis of Indole Annulated Benzazepine Derivative of Medicinal Interest

The ubiquity of benzazepines in medicinal chemistry is undoubtedly a consequence of the multifarious biological response which they elicit in combating a variety of body ailments.A benzazepine derivative-‘Fenoldopam mesylate’has emerged as avasodilator in peripheral arteries ansd as a diuretic in th...

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Bibliographic Details
Published in:Oriental journal of chemistry 2013, Vol.29 (4), p.1643-1646
Main Authors: Vandana, Aditi, Yadav, Yogita, Kishore, D
Format: Article
Language:English
Subjects:
Aromatic compounds
Arteries
Hydrocarbons
Kidneys
Organic chemistry
Synthesis
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Summary:The ubiquity of benzazepines in medicinal chemistry is undoubtedly a consequence of the multifarious biological response which they elicit in combating a variety of body ailments.A benzazepine derivative-‘Fenoldopam mesylate’has emerged as avasodilator in peripheral arteries ansd as a diuretic in the kidneys. This discovery provided an optimism for the search of other novel agents from benzazepine class of compounds which could show a higher level of medicinal efficacy.The proposed synthesis (scheme-1) , in its first step was propelled forward with the formation of compound 1.3(which resulted from the reaction of succinyl chloride and p-fluoroaniline).The reaction of 1.3 with ethyl formate in the presence of a base formed 1.4 which underwent Japp-Klingemann reaction with aryl diazonium chloride followed by cyclocondensation with acid under the conditions of Fischer indolization to give indole substituted derivative 1.5.
ISSN:0970-020X
2231-5039
DOI:10.13005/ojc/290451