Biyolojik aktif substitüe dion bileşiklerinin sentezi
Synthesis of biologically active substituted dione
Yazar: DİLAN GEZER
Danışman: PROF. DR. ZELİHA GÖKMEN
İstanbul Üniversitesi-Cerrahpaşa / Lisansüstü Eğitim Enstitüsü / Kimya Ana Bilim Dalı / Organik Kimya Bilim Dalı
Derece: Yüksek Lisans, 2022
Konu: Kimya = Chemistry
Dizin: Naftalin = Naphthalene ; Organik sentez = Organic synthesis ; Pirolidinler = Pyrrolidines

Özet:
Çalışmamızda çeşitli pirol-2,5-dion ve naftalen-1,4-dion bileşiklerinin azotlu heterosiklik  amin bileşikleri ile belirli şartlar ortamında tepkimeleri gözlemlenmiştir.
Deneysel çalışmalarımızda başlangıç maddesi olarak kullanılan 1-fenilpirol-2,5-dion (1), 3,4-dikloro-1-fenil-pirol-2,5-dion (2), 2,3-dibromo-naftalen-1,4-dion (3) bileşikleri ile azotlu heterosiklik amin bileşiklerden aza-sübstitüe dion bileşikleri elde edilmiştir.
1-fenilpirol-2,5-dion (1)'in; 1-piperonilpiperazin, 1-(2-furoil) piperazin ile tepkimelerinden  sırasıyla; 3-(4-benzo[d][1,3]dioxol-5-ilmetil)piperazin-1-il)-1-fenilpirolidin-2,5-dion (4) 3-(4-(furan-2-karbonill)piperazin-1-il)-1-fenil-1H-pirolidin-2,5-dion (5).
 3,4-dikloro-1-fenil-pirol-2,5-dion (2)'in; 1-(3-hidroksifenil)piperazin,1-[Bis(4-florofenil)-metilpiperazine, 1-(2-piridinil)piperazin, 1-(4-triflorometilfenil)-piperazin,1-(3-florofenil)-piperazin, 2-tiyofen metilamin, 4,4'-Bis(3-aminofenoksi)difenil sulfon, 4-aminotetrahidropiran ile tepkimelerinden sırasıyla; 3-kloro-4-(4-(3-hidroksifenil)piperazin-1-il)-1-fenil-1H-pirol-2,5-dion(6), 3-(4(bis(4-florofenil)metil)piperazin-1-il)-4-kloro-1-fenil-1H-pirol-2,5-dion (7), 3-kloro-1-feni-l-4-(4-(piridin-4-il)piperazin-1-il)-1H-pirol-2,5-dion (8), 3-kloro-1-fenil-4-(4-(4-triflorometil)-fenil)-piperazin-1-il)-1H-pirol-2,5-dion (9), 3-kloro-4-(4-(3-florofenil)piperazin-1-il)-1-fenil-1H-pirol-2,5-dion (10) 3-kloro-4-((3-(4-((4-(3-diazenil-fenoksi)fenil)sulfonil)-fenoksi)fenil)-amino)-1-fenil-1H-pirol-2,5-dion (11), 3-kloro-1-fenil-4-((tiyofen-2-ilmetil)amino)-1H-pirol-2,5-dion (12), 3-kloro-1-fenil-4-((tetrahidro-2H-piran-4-il)amino)1H-pirol-2,5-dion (13). 
2,3-dibromo-naftalen-1,4-dion (3)'ün 4-aminotetrahidropiran ile tepkimesinden 2-bromo-3-(((tetrahidro-2H-piran-4-il)amino)-naftalen-1,4-dion (14) bileşiği sentezlenmiştir.
Tepkime sonucu sentezlenen onbir (11) adet yeni bileşik kromatografik yöntemleriyle saflaştırıldı.Yapıları spektroskopik (IR, MS, NMR (1H ve 13C))  analiz yöntemleriyle ortaya çıkarılmıştır.

Abstract:
in our study, it was observed that various pyrrole-2,5-dione and naphthalene-1,4-dione growers reacted with nitrogenous heterocyclic amines under sensitive conditions.
1-phenylpyrrole-2,5-dione (1), 3,4-dichloro-1-phenyl-pyrrole-2,5-dione (2), 2,3-dibromo-naphthalene-1, Aza-substituted dione compounds were obtained from 4-dione (3) compounds and nitrogenous heterocyclic amine compounds.
3-(4-benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-1phenylpyrrolidine-2,5-dione (4) 3-(4-(furan-2-carbonyl)piperazin-1-yl)-1-phenyl-1H-pyrrolidine-2,5-dion (5) were synthesized by the reaction of compounds 1-phenyl pyrrole-2,5-dione (1); 1-piperonylpiperazine, 1-(2-furoyl) piperazine in order of.
3-chloro-4-(4-(3-hydroxyphenyl)piperazin-1-yl)-1-phenyl-1H-pyrrole-2,5-dione (6) 3(4(bis(4fluorophenyl)methyl)piperazin-1-yl)-4-chloro-1-phenyl-1H-pyrrole-2,5-dione (7) 3-chloro-1-phenyl-4-(4-(pyridin-4-yl)piperazin-1-yl)-1H-pyrrole-2,5-dione (8) 3-chloro-1-phenyl-4-(4-(4-trifluoromethyl)phenyl)piperazin-1-yl)-1H-pyrrole-2,5-dione (9) 3-chloro-4-(4-(3-fluorophenyl)piperazin-1-yl)-1-phenyl-1H-pyrrole-2,5-dione (10)  3-chloro-4-((3-(4-((4-(3-diazenyl-phenoxy)phenyl)sulfonyl)-phenoxy)phenyl)-amino)-1-phenyl-1H-pyrrole-2,5-dione (11) 3-chloro-1-phenyl-4-((thiophen-2-ylmethyl)amino)-1H-pyrrole-2,5-dione (12) 3-chloro-1-phenyl-4-((tetrahydro-2H-pyran-4-yl)amino)1H-pyrrole-2,5-dione (13) were synthesized by the reaction of compounds 3,4-dichloro-1-phenyl-pyrrole-2,5-dione (2) and  1(3-hydroxyphenyl)piperazine, 1-[Bis(4-fluorophenyl)methylpiperazine, 1-(2-pyridinyl)pipe-razine, 1-(4-trifluoromethylphenyl)-piperazine, 1-(3-fluorophenyl))piperazine, 2-thiophene methylamine,  4,4'-Bis(3-aminophenoxy)diphenylsulfone, 4-Aminotetrahydropyran in order of.
Eleven(11) new compounds synthesized as a result of the reaction were purified by chromatographic process. Their structures were revealed by spectroscopic (IR, MS, NMR (1H and 13C)) analysis process.