Synthesis and characterization of novel 2,3 Dı (Subtituted) naphthoquinone compounds

Abstract

Bu çalışmada, yeni sübstitüe naftakinon bileşikleri, N-, S- nükleofilleri ile dört başlangıç maddeleri olan naftakinon bileşiklerinin reaksiyonları ile sentezlenmiştir.2-(1-(2-siyanofenil)piperazinil)-3-kloro-1,4-naftakinon bileşiği (2), 2,3-diklor-1,4-NQ bileşiği (1)' nin 1-(2-siyanofenil)piperazin bileşiğinin reaksiyonu ile sentezlendi. Bu bileşik yeni bir bileşiktir ve başlangıç maddesi olarak kullanılmıştır.Yeni 2-(1-(2-siyanofenil)piperazinil)-3-(2-hidroksietiltiyo)-1,4-NQ (3), 2-(1-(2-siyano-fenil)piperazinil)-3-(4-hidroksibütiltiyo)-1,4-NQ (4), 2-(1-(2-siyanofenil)piperazinil)-3-(2-hidroksi-1-propiltiyo)-1,4-NQ (5) ve 2-(1-(2-siyanofenil)piperazinil)-3-(6-hidroksiheksiltiyo)-1,4-NQ (6) bileşikleri (2) bileşiğinin EtOH/Na2CO3' da bazı S-nükleofiller (2-merkaptoetanol, 4-merkapto-1-bütanol, 1-merkapto-2-propanol, 6-merkaptoheksanol) ile reaksiyonundan sentezlendi.2,3-Diklor-1,4-NQ (1) ile 6-amino-1-heksanol'un reaksiyonundan bilinen 2-(6-aminoheksil-1-ol)-3-kloro-1,4-NQ bileşiği (7) sentezlenmiştir. Yeni 2-(6-aminoheksil-1-ol)-3-(2-hidroksietiltiyo)-1,4-NQ (8), 2-(6-aminoheksil-1-ol)-3-(4-hidroksibutiltyio)-1,4-NQ(9), 2-(6-aminoheksil-1-ol)-3-(6-hidroheksiltiyo)-1,4-NQ (10), 2-(6-aminoheksil-1-ol)-3-(11-hidroksiundesiltiyo)-1,4-NQ (11), 2-(6-aminoheksil-1-ol)-3-(2-klorobenzenmetiltiyo)-1,4-NQ (12) ve 2-(6-aminoheksil-1-ol)-3-(2-feniletiltiyo)-1,4-NQ (13) bileşikleri (7) bileşiğinin sırasıyla 2-merkaptoetanol, 4-merkapto-1-bütanol, 6-merkaptoheksanol, 11-merkapto-1-undekanol, 2-klorobenzilmerkaptan ve 2-fenil-etantiyol reaksiyonundan elde edildi.Bilinen 2-(1-piperonilpiperazin-1-ol)-3-kloro-1,4-NQ bileşiği (14), 2,3-diklor-1,4-naftakinon(NQ) (1) bileşiğinin 1-piperonilpiperazin ile kloroformda oda sıcaklığında reaksiyondan sentezlendi. Yeni 2-(1-piperonilpiperazin-1-ol)-3-(2-hydroksietiltiyo)-1,4-NQ (15),2-(1-piperonilpiperazin-1-ol)-3-(4-hidroksibütiltiyo)-1,4-NQ (16), 2-(1-piperonilpip-erazin-1-ol)-3-(6-hidroksi-heksiltiyo)-1,4-NQ (17),2-(1-piperonilpipe-razin-1-ol)-3-(2-hidroksi-1-propiltiyo)-1,4-NQ (18) ve 2-(1-piperonilpiperazin-1-ol)-3-(11-hidroksiundesiltiyo)-1,4-NQ (19) bileşikleri (14) bileşiğinin S-nükleofiller ( 2-merkaptoetanol, 4-merkapto-1-bütanol, 6-merkaptoheksanol, 1-merkapto-2-propanol, 11-merkapto-1-undekanol ) ile reaksiyonundan kazanıldı.Sentezlenen yeni onaltı bileşik kromatografik yöntemlerle saflaştırılmıştır. Bileşiklerin yapısı MS, IR, 1H NMR ve 13C NMR vb. spektroskopik yöntemler ile incelendi. Aralık 2018, 142 sayfa.Anahtar kelimeler: Naftakinon türevleri, N-nükleofiller, S-nükleofiller, 2,3-Disübstitüe-1,4-naftakinon bileşikleri.

SYNTHESIS AND CHARACTERIZATION OF NOVEL 2,3- DI(SUBSTITUTED)NAPHTHOQUINONE COMPOUNDSIn this study, new substituted naphthoquinone compounds were synthesized by the reactions of N- , S- nucleophiles with 2,3-dichloro-1,4-naphthoquinone and other naphthoquinone compounds which were used as starting materials.The new 2-(1-(2-cyanophenyl)piperazinyl)-3-chloro-1,4-naphthoquinone compound (2) was synthesized by the reaction of 2,3-dichloro-1,4-naphthoquinone compound (1) with 1-(2-cyanophenyl)piperazine. The new compound (2) was used as starting material to prepare the following new compounds: 2-(1-(2-cyanophenyl)piperazinyl)-3-(2-hydroxyethylthio)-1,4-naphthoquinpne (3), 2-(1-(2-cyanophenyl)piperazinyl)-3-(4-hydroxybutylthio)-1,4-naphthoquinpne (4), 2-(1-(2-cyanophenyl)piperazinyl)-3-(2-hydroxy-1-propylthio)-1,4-naphthoquinpne (5), 2-(1-(2-cyanophenyl)piperazinyl)-3-(6-hydroxyhexylthio)-1,4-naphthoquinpne (6), by carrying out reactions with the following nucleophiles respectively: 2-mercaptoethanol, 4-mercapto-1-butanol, 1-mercapto-2-propanol, 6-mercapto-1-hexanol.2,3-Dichlori-1,4-naphthoquinone (1) was reacted with 6-aminohexane-1-ol, and known 2-(6-aminohexyl-1-ol)-3-chloro-1,4-naphthoquinone compound (7) was synthesized. This known compound was used as starting material to prepare the following new compounds: 2-(6-aminohexyl-1-ol)-3-(2-hydroxyethylthio)-1,4-naphthoquinone (8), 2-(6-aminohexyl-1-ol)-3-(4-hydroxybutylthio)-1,4-naphthoquinone (9), 2-(6-aminohexyl-1-ol)-3-(6-hydroxyhexylthio)-1,4-naphthoquinone (10), 2-(6-aminohexyl-1-ol)-3-(11-hydroxyundecylthio)-1,4-naphthoquinone (11), 2-(6-aminohexyl-1-ol)-3-(2-chlorobenzenemethylthio)-1,4-naphthoquinone (12), 2-(6-aminohexyl-1-ol)-3-(2-phenylethylthio)-1,4-naphthoquinone (13), by carrying out reactions with the following nucleophiles respectively: 2-mercaptoethanol, 4-mercapto-1-butanol, 6-mercapto-1-hexanol, 11-mercapto-1-undecanol, 2-chlorobenzylmercaptan, 2-phenyl-ethanthiol.2,3-Dichloro-1,4-naphthoquinone (1) was reacted with 1-piperonyl piperazine, and known 2-(1-piperonylpiperazin-1-yl)-3-chloro-1,4-naphthoquinone compound (14) was synthesized. This known compound was used as starting material to prepare the following new compounds: 2-(1-piperonylpiperazin-1-yl)-3-(2-hydroxyethylthio)-1,4-naphthoquinone (15), 2-(1-piperonylpiperazin-1-yl)-3-(4-hydroxybutylthio)-1,4-naphthoquinone (16), 2-(1-piperonylpiperazin-1-yl)-3-(6-hydroxyhexylthio)-1,4-naphthoquinon (17), 2-(1-piperonylpiperazin-1-yl)-3-(2-hydroxy-1-propylthio)-1,4-naphthoquinon (18), 2-(1-piperonylpiperazin-1-yl)-3-(11-hydroxyundecylthio)-1,4-naphthoquinon (19), by carrying out reactions with the following nucleophiles respectively: 2-mercaptoethanol, 4-mercapto-1-butanol, 6-mercapto-1-hexanol, 1-mercapto-2-propanol, 11-mercapto-1-undecanol.The new compounds which were synthesized were purified by chromatographic methods and the structure of these compounds were determined by using spectroscopic methods (MS, IR, 1H-NMR, 13C-NMR).October 2018, 118 pages.Keywords: Naphthoquinone, N-nucleophile, S-nucleophile, 2,3-Dichloro-1,4- naphthoquinone.