Tez özetleri Astronomi ve Uzay Bilimleri Anabilim Dalı

The Synthesıs of Some Novel N-, S-, O- Substıtuted Naphthaquınone Compounds

In this study, the unknown new substituted quinone compounds were synthesized by reaction of (N-,S-,O-) nucleophiles with 2,3-dichloro-1,4-naphthaqunone was used as starting materials to synthesis of new quinone compounds.
The known 2-chloro-3-(4-(diethylamino) phenylamino)-1,4-naphthoquinone (2) was synthesized by reaction of 2,3-Dichloro-1,4-naphthoquinone (1) with N.N-dimethyl phenylene diamine. Unknown new 2-Ethanthio-3-(4-(diethyl amino) phenyl amino)-1,4-naphthoquinone (3) was synthesized by reaction of 2-chloro-3-(4-(diethylamino) phenylamino)-1,4-naphthoquinone (2) with Ethantiol. The unknown new 2-(7-sulphonyl-4-methyl coumarinyl)-3-(4-(diethylamino)phenylamino)-1,4-naphthoquinone (4) was synthesized by reaction of 2-chloro-3-(4-(diethylamino) phenylamino)-1,4-naphthoquinone (2) with 7-mercapto-4-methyl coumarin. Unknown new 2-(1-propanthio)-3-(4-(diethylamino)phenylamino)1,4-naphthoquinone (5) was synthesized by reaction of 2-chloro-3-(4-(diethylamino) phenylamino)-1,4-naphthoquinone (2) with propanthiyol. Unknown new 2-(1-butanthio)-3-(4-(diethylamino)phenylamino)-1,4-naphthoquinone (6) was synthesized by reaction of 2-chloro-3-(4-(diethylamino) phenylamino)-1,4-naphthoquinone (2) with Butanthiol. Unknowen new 2-(1-octanthio)-3-(4-(diethylamino)phenylamino)-1,4-naphthoquinone (7) was synthesized by reaction of 2-chloro-3-(4-(diethylamino) phenylamino)-1,4-naphthoquinone (2) with octanthiol. Unknowen new 2-(2-(aminopiperidenyl)-3-chloro-1,4-naphthoquinone (8), 2-chloro-3-((1-(1,4-dioxi-3-piperiden-2-ylmethylamino)-1,4-dihydrophthalin-2-yl)methylamino)-1,4- naphthoquinone (9) and 2-(2-(aminopiperidenyl)-3-ethoxy-1,4-naphthoquinone (10) were synthesized by reaction of 2,3-dichloro-1,4-naphthoquinone (2) with 2-(aminomethyl) piperiden. Unknowen new 2-(2-methyl indol)-3-chloro-1,4-naphthoquinone (11) and 2-(2-methyl indol)-3-methoxy-1,4-naphthoquinone (12) were synthesized by reaction of 2,3-dichloro-1,4-naphthoquinone (1) with 2-methyl indol. Unknowen new 2-(2,2’-(ethylenedioxy) bis (ethyleneamine)-3-chloro-1,4-naphthoquinone (13) and 2,2’-(2,2’(Ethylenedioxy) bis (Ethyleneamine)-3,3’-Dichloro-bis(1,4-naphthoquinone) (14) were synthesized of 2,3-dichloro-1,4-naphthoquinone (1) with 2,2’-(ethylenedioxy)bis(ethyleneamine). Unknown new 2,2’-(2,2’(ethylenedioxy) bis (Ethylene amine)-3,3’-bis(butanthio) bis (1,4-naphthoquinone) (15) was synthesized by reaction of 2,2’-(2,2’(Ethylenedioxy) bis (Ethyleneamine)-3,3’-Dichloro-bis (1,4 naphthoquinone) (14) with butanthiol. Unknown new 2,2’-(2,2’(Ethylenedioxy) bis (Ethyleneamine)-3,3’-bis(octanthio) bis (1,4-naphthoquinone) (16) was synthesized by reaction of 2,2’-(2,2’(Ethylenedioxy) bis (Ethyleneamine)-3,3’-Dichloro-bis(1,4 naphthoquinone) (14) with Octanthiol. Known 2-chloro-3-(1-methyl piperazinyl)-1,4-naphthoquinone (17) was synthesized by reaction of 2,3-dichloro-1,4-naphthoquinone (1) with 1-methyl piperazine. Unknown new 2-(4-methylphenyl thio)-3-(1-methyl piperazinyl)-1,4-naphthoquinone (18) was synthesized by reaction of 2-chloro-3-(1-methyl piperazinyl)-1,4-naphthoquinone (17) with 4-methyl benzene thiol. Unknown new 2-(1-Butanthio)-3-(1-methyl piperazinyl)-1,4-naphthoquinone (19) was synthesized by reaction of 2-chloro-3-(1-methyl piperazinyl)-1,4-naphthoquinone (17) with 1-Butanthiol. Unknown new 3-N-(3-(Dimethylaminomethyl) indol)-2-chloro-1,4-naphthoquinone (20) was synthesized by reaction of 2,3-dichloro-1,4-naphthoquinone (1) with 3-((Dimethyl amino) methyl) indol. Unknown new 3-N-(3-(Dimethylaminomethyl) indol)-2-Butan-1,4-naphthoquinone (21) was synthesized by reaction of 3-N-(3-(Dimethylaminomethyl) indol)-2-chloro-1,4-naphthoquinone (20) with Butanthiol. Unknown new 2-(2-Amino benzyl alchol)-3-chloro-1,4-naphthoquinone (22) was synthesized by reaction of 2,3-dichloro-1,4-naphthoquinone (1) with 2-amino benzyl alchol. Unknown new 2-(2-amino benzyl alchol)-3-butan thio-1,4-naphthoquinone (23) was synthesized by reaction of 2-(2-Amino benzyl alchol)-3-chloro-1,4-naphthoquinone (22) with 1-Butanthiol. Unknown new 2-(2-amino benzyl alchol)-3-propanthio-1,4-naphthoquinone (24) was synthesized by reaction of 2-(2-Amino benzyl alchol)-3-chloro-1,4-naphthoquinone (22) with 1-Propanthiol. Unknown new 2-(2-(2-Hydroxy ethyl) phenylamino)-3-chloro-1,4-naphthoquinone (25) 2,3-Dichloro-1,4-naphthoquinone (1) N-(2-hydroxy ethyl)aniline. Known 2-(2-(Diethyl amino)ethylamino)-3-chloro-1,4-naphthoquinone (26) was synthesized by reaction of 2,3-Dichloro-1,4-naphthoquinone (1) with N,N-Diethylethylene amine. Unkown new 2-(2-(Diethylamino) ethylamino)-3-(1-octanthio)-1,4-naphthoquinone (27) was synthesized by reaction of 2-(2-(Diethyl amino) ethylamino)-3-chloro-1,4 naphthoquinone (26) with 1-Octanthiol. Unkown new 2-(2-(Diethylamino) ethylamino)-3-(1-butanthio)-1,4-naphthoquinone (28) was synthesized by reaction of 2-(2-(Diethyl amino) ethylamino)-3-chloro-1,4 naphthoquinone (26) with 1-Butanthiol.
The structure of novel synthesized quinone compounds was determined by using micro analysis, ¹H-NMR, ¹³C-NMR, FT-IR and MS techniques.