İnvestigation of reaction conjugate cyclic diones with some (N-,S,and O-) nuchleopiles

In this study, the reactions of DCNQ (1) compound with aliphatic/aromatic/heterocyclic amine and mercaptan compounds at room temperature were examined, and N-, N,N-, N,S-, S- and S,S-(substituted)-NQ compounds were obtained. DCNQ (1) compound (1-(3-hydroxyphenyl)piperazine (2), 3,4-dichlorophenylpiperazine (4), 1-(2-ethoxyethyl)piperazine (6), 1-(4-trifluoromethylphenyl)piperazine (8) , 1-(2-pyridinyl)-piperazine (10), 1-phenylpiperazine (12), 1-(4-amino-phenyl)-piperazine (14) and 4-benzyl-piperidine (16), 2-thiophenmethylamine (30), 3-hidrokxypropylamine (18), 4-hidroxybutylamine (20) ve 6-hidroxyhexylamine (22)and triethylenetetramine (23) 2-(1-(3-hydroxy-phenyl)piperazine)-3-chloro-NQ (3), 2-[1-(3,4-dichlorophenyl)piperazin-1-yl]-3-chloro-NQ (5), 2-chloro-3-(4-(2-ethoxyethyl)piperazin-1-yl)-NQ (7), 2-chloro-3-(4-(4-(trifluoromethyl-phenyl)piperazin-1-yl)-NQ (9), 2-chloro-3-(4-(pyridin-2-yl)piperazin-1-yl)-NQ (11), 2-chloro-3-(4-phenylpiperazin-1-yl)-NQ (13), 2-chloro-3-(4-phenylpiperazin-1-yl)-NQ (15), (2-(4-benzylpiperidin-1-yl)-3-chloro-NQ (17), 2,3-bis ((thiophene-2-ylmethyl)amino)-NQ (31), 2-chloro-3-((3-aminohidroxypropyl)amino)-NQ (19), 2-chloro-3- ((4-hidroxybuthyl)amino-NQ (21), 2-chloro-3-(6-hydroxyhexylamino)-NQ (23), 3,3'-(((ethane-1,2-diylbis(azandiyl))bis(ethane-2,1-diyl))bis-(azandiyl))bis(2-chloro-NQ) (25) N-, N,N-(substituted)-NQ compounds; mercapto-2-propanol (26), 4-mercapto-1-butanol (28), 4-t-butyl-benzylmercaptan (32), 2-ethylhexylmercaptan (34) and 2-phenylethylmercaptan (36) as well as 2-[1-(6-amino-hexyl-1-ol]-3-(2-hydroxy-propylthio)-NQ (27), 2-(1-(3,4-dichlorophenyl)-piperazinyl)-3-(4-hydroxybutyl-thio)-NQ (29), 2-(1-(4-t-butyl-benzylthio)-3-chloro-NQ (33), 2,3-bis((2-ethylhexylthio)-NQ (35) and 2,3-bis-(phenylthio)-NQ (37) N,S-, S-S,S-(substituted)-NQ compounds were synthesized. Different synthesis methods were applied in the synthesis steps based on the type of nucleophile. In the reaction with N-nucleophiles, DCNK (1), (5), and (8) compounds were reacted with aliphatic/aromatic/heterocyclic amine compounds in a 1:1 molar ratio. The reactions were carried out at room temperature in 30 mL CHCl3 for 12 hours to 1 day, and the reaction completion was monitored by Thin-layer chromatography (TLC). In the reaction with S-nucleophiles, DCNK (1), (5), and (8) compounds were reacted with mercaptan compounds in a 1:1 molar ratio. The reactions were carried out at room temperature in 30 mL Na2CO3/EtOH for 12 hours to 1 day, and the reaction completion was monitored by Thin-layer chromatography (TLC). The synthesized compounds were purified by chromatographic and spectroscopic analysis techniques (IR, MS, 1H NMR, 13C NMR) were used in structure determination.