2011 YÜksek lisans tez özetleri

The Synthesıs Of Naphthoquınone Derıvatıves From Some Hıgh-Carbon Alıphatıc Thıols And Amınes

That we have done in this study, reactions of aliphatic thiol and amine compounds with 2,3-dichloro-1,4-naphthoquinone as a starting compound, were investigated.

The known and unknown new substituted-naphthoquinone compounds were synthesized by reactions of S-, N-, S,N- nucleophiles with naphthoquinones. 2,3-Dichloro-1,4-naphthoquinone was used as starting material to synthesis of new naphthoquinone compounds.

In the first step of this study, firstly 2,3-dichloro-1,4-naphthoquinone (1) compound was reacted with hexadecanethiol and unknown novel 2-chloro-3-(hexadecylthio)naphthalene-1,4-dione (2) and 2,3-bis(hexadecylthio)naphthalene-1,4-dione (3) and 2-ethoxy-3-(hexadecylthio)naphthalene-1,4-dione (4) compounds that known in the literature, was obtained. 2,3-Dichloro-1,4-naphthoquinone (1) compound was reacted with octadecanethiol and 2-chloro-3-(octadecylthio)naphthalene-1,4-dione (5), 2,3-bis(octadecylthio)naphthalene-1,4-dione (6) and 2-ethoxy-3-(octadecylthio)naphthalene-1,4-dione (7) compounds that known in the literature, were obtained. The novel compounds 2-(hexadecylthio)-3-((2-morpholinoethyl)amino)naphthalene-1,4-dione (8) and 2-(octadecylthio)-3-((2-morpholinoethyl)amino)naphthalene-1,4-dione (9) were synthesized from the reactions of compounds 2-chloro-3-(hexadecylthio)naphthalene-1,4-dione (2) and 2-chloro-3-(octadecylthio)naphthalene-1,4-dione (5) with 4-(2-aminoethyl)-morpholin respectively.

In the second step of this study, mono amine naphthoquinone compounds were synthesized and high-carbon thiols were added to this compounds.

2,3-Dichloro-1,4-naphthoquinone (1) compound was reacted with aniline and 2-chloro-3-(phenylamino)naphthalene-1,4-dione (10) that known in the literature, was synthesized. The novel compounds 2-(hexzadecylthio)-3-(phenilamino)naphthalene-1,4-dione (11) and 2-(octadecylthio)-3-(phenilamino)naphthalene-1,4-dione (12) were synthesized from the reactions of compound 2-chloro-3-(phenylamino)naphthalene-1,4-dione (10) with hexadecanethiol and octadecanethiol respectively. 2,3-Dichloro-1,4-naphthoquinone (1) compound was reacted with 4-fluoroaniline and 2-(chloro)-3-((4-fluorophenyl)amino)naphthalene-1,4-dione (13) that known in the literature, was synthesized. The novel compounds 2-((4-fluorophenyl)amino)-3-(hexzadecylthio)naphthalene-1,4-dione (14) and 2-((4-fluorophenyl)amino)-3-(octadecylthio)naphthalene-1,4-dione (15) were synthesized from the reactions of compound 2-(chloro)-3-((4-fluorophenyl)amino)naphthalene-1,4-dione (13) with hexadecanethiol and octadecanethiol respectively. 2,3-Dichloro-1,4-naphthoquinone (1) compound was reacted with 4-fluorobenzylamine and 2-chloro-3-((4-fluorobenzyl)amino)naphthalene-1,4-dione (16) that known in the literature, was synthesized. The novel compounds 2-((4-fluorobenzyl)amino)-3-(hexadecylthio)naphthalene-1,4-dione (17) and 2-((4-fluorobenzyl)amino)-3-(octadecylthio)naphthalene-1,4-dione (18) were synthesized from the reactions of compound 2-chloro-3-((4-fluorobenzyl)amino)naphthalene-1,4-dione (16) with hexadecanethiol and octadecanethiol respectively. 2,3-Dichloro-1,4-naphthoquinone (1) compound was reacted with β-naphthylamine and 2-chloro-3-(naphthalen-2-ylamino)naphthalene-1,4-dione (19) that known in the literature, was synthesized. The novel compounds 2-(hexadecylthio)-3-(naphthalen-2-ylamino)naphthalene-1,4-dione (20) and 2-(naphthalen-2-ylamino)-3-(octadecylthio)naphthalene-1,4-dione (21) were synthesized from the reactions of compound 2-chloro-3-(naphthalen-2-ylamino)naphthalene-1,4-dione (19) with hexadecanethiol and octadecanethiol respectively. 2,3-Dichloro-1,4-naphthoquinone (1) compound was reacted with o-toluidine and 2-chloro-3-(o-tolylamino)naphthalene-1,4-dione (22) that known in the literature, was synthesized. The novel compounds 2-(hexadecylthio)-3-(o-tolylamino)naphthalene-1,4-dione (23) and 2-(octadecylthio)-3-(o-tolylamino)naphthalene-1,4-dione (24) were synthesized from the reactions of compound 2-chloro-3-(o-tolylamino)naphthalene-1,4-dione (22) with hexadecanethiol and octadecanethiol respectively. 2,3-Dichloro-1,4-naphthoquinone (1) compound was reacted with m-toluidine and 2-chloro-3-(m-tolylamino)naphthalene-1,4-dione (25) that known in the literature, was synthesized. The novel compounds 2-(hexadecylthio)-3-(m-tolylamino)naphthalene-1,4-dione (26) and 2-(octadecylthio)-3-(m-tolylamino)naphthalene-1,4-dione (27) were synthesized from the reactions of compound 2-chloro-3-(m-tolylamino)naphthalene-1,4-dione (25) with hexadecanethiol and octadecanethiol respectively.

The novel synthesized naphthoquinone compounds were purified by chromatographic methods. The structures of compounds were determined by using micro analysis and spectroscopic methods (IR, ¹H-NMR, ¹³C-NMR, MS).