Synthesis of indole annulated benzazepine derivative of medicinal interest

Abstract

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.