RETRACTED ARTICLE: Synthesis and characterization of new compounds derived from 1H-indol-5-ylamine

Abstract

Recently, indoles are considered interesting heterocyclic compounds due to their wide range of biological activities such as antimicrobial activity. Herein, some new indole derivatives containing heterocyclic moieties were synthesized using 1H-indol-5-ylamine as a starting material, then allowed to convert to diazonium salt (1) which used for synthesis of new azo dyes (2, 3 and 4) by coupling with salicylaldehyde, o-cresol and phenol. The reaction of diazonium salt (1) with acetyl acetone afforded hydrazine (5) which was reacting with active methylene compounds (malononitrile, ethyl cyanoacetate) to give pyridazine derivatives (8, 9). The reaction of parent compound with thioisocyanate was produced Compound (10) which cyclized with phenacyl bromide to form thiazole derivative (11). Treatment of parent compound with hydrazine was gave compound (12) which consider as a key for many Schiff bases (13, 14, 15 and 16) and its derivatives such as oxazepine, thiazolidinone, β-lactam and pyrazol derivatives (17, 18, 19 and 20), respectively.Compound (14) under went to react with active methylene compounds (malononitrile, ethyl acetoacetate) to afford derivatives (21, 22) while when (14) was treated with hydroxyl amine in presence of sodium acetate gave (23). The latter was produced derivatives (24, 25) when treated with benzoyl chloride, benzyl chloride, respectively, while was afforded (26) when allowed to react with acetic anhydride. At last treatment of (26) with hydrazine formed derivative (27). The structures, of all synthesized compounds were confirmed using spectroscopic analysis such as UV, FTIR, ¹HNMR and ¹³C–NMR.