Synthesis of Novel 3,4-Dihydroquinolin-2(1H)-one Guanidines as Potential Antihypertensive Agents

Abstract

Hydroxy-3,4-dihydroquinolin-2(1H)-ones (4a-c) were synthesized by intramolecular Friedel Craft alkylation of N-(methoxyphenyl)-3-chloropropionamides (3a-c), obtained by acylation of anisidine with chloropropionyl chloride. The hydroxy-3,4-dihydro quinolin-2(1H)-ones (4a-c) were treated with various dibromo alkanes under phase transfer catalyst conditions at room temperature to give bromoalkyloxy-3,4-dihydroquinolin-2(1H)-ones (5a-l) which on further reaction with guanidine hydrochloride in dimethyl formamide afforded N-{4-[(2-oxo-1,2,3,4- tetrahydroquinolin-5-yl)oxy]alkyl}guanidines (6a-l). These compounds were synthesized as potential antihypertensive agents.