Kalkonoid benzeri maddelerin sentezi ve 4π fotosiklizasyon reaksiyonları
Synthesis of chalconoid like compounds and 4π photocyclization reactions
Yazar: SERPİL ÖZKURT SİVRİKAYA
Danışman: PROF. DR. NURETTİN YAYLI
Karadeniz Teknik Üniversitesi / Fen Bilimleri Enstitüsü / Fen Bilgisi Eğitimi Ana Bilim Dalı
Derece: Doktora, 2004
Konu: Eğitim ve Öğretim = Education and Training

Özet:
Bu çalışmanın birinci bölümünde kalkonoid benzeri 10 adet madde (1-10); (2E,4E)- l,5-difenilpenta-2,4-dien-l-on (1), (2£,4£)-l-(2-nitro)fenil-5-fenilpenta-2,4-dien-l-on (2), (2£:,4£)-l-(3-nitro)fenil-5-fenilpenta-2,4-dien-l-on (3), (2£,4^-l-(4-nitro)fenil-5- fenilpenta-2,4-dien-l-on (4), (2£'54JE)-l-(2-metoksi)fenil-5-fenilpenta-2,4-dien-l-on (5), (2£,4£)-l-(3-metoksi)fenil-5-fenilpenta-2,4-dien-l-on (6), (2£,4£)-l-(4-metoksi)fenil-5- fenilpenta-2,4-dien-l-on (7), (2£,4£)-l-(2-metil)fenil-5-fenilpenta-2,4-dien-l-on, 8, (2£,4JE)-l-(3-metil)fenil-5-fenilpenta-2,4-dien-l-on (9), (2£,4^)-l-(4-metil)fenil-5- fenilpenta-2,4-dien-l-on (10), Claisen-Schmidt reaksiyonuna göre sentezlendi. Yapılan literatür araştırması sonucuna göre 2, 8 ve 9 nolu maddelerin yeni ve 1, 3, 4, 5, 6, 7 ve 10 nolu maddelerin ise bilinen maddeler olduğu tespit edildi. Çalışmanın ikinci bölümünde sentezlenen Kalkon benzeri (2E,4E)-l,5~diaril-2,4- pentadien-1-on bileşiği ve türevlerinden fotokimyasal elektrosiklik reaksiyonları sonucu kiral siklobüten yapısında yeni 10 adet madde (11-20) sentezlendi. Bu maddeler; rel-cis- 3-benzoil-4-fenil-l-siklobüten (11), rel-cis-3-(2-nitro)benzoil-4-fenil-l -siklobüten (12), rel-cis-3-(3-nitro)benzoil-4-fenil- 1 -siklobüten (13), rel-cis-3-(4-nitro)benzoil-4-fenil- 1 - siklobüten (14), rel-cis-3-(2-metoksi)benzoil-4-fenil-l -siklobüten (15), rel-cis-3-(3- metoksi)benzoil-4-fenil- 1 -siklobüten (16), rel-cis-3-(4-metoksi)benzoil-4-fenil- 1 - siklobüten (17), rel-cis-3-(2-metil)benzoil-4-fenil-l -siklobüten (18), rel-cis-3-(3-metil) benzoil-4-fenil-l -siklobüten (19), rel-cis-3-(4-metil)benzoil-4-fenil-l -siklobüten (20), olarak adlandırıldı. Sentezlenen maddelerin yapılan spektroskopik olarak NMR, FT-IR, UV ve LC-MS/MS teknikleri kullanılarak aydmlatıldı. Anahtar Kelimeler: Kalkonoidler, Dihidrokalkon, Kiral, Siklobüten, NMR, LC-MS/MS. IV

Abstract:
Synthesis of Chalconoid Like Compounds and 4% Photocyclization Reactions In the first part of this work, 10 chalconoid like compounds (1-10); (2E,4E)-1,5- diphenylpenta-2,4-dien- 1 -one (1), (2E,4E)- 1 -(2-nitro)phenyl-5-phenylpenta-2,4-dien- 1 -one (2), (2E,4E)-l-(3-nitro)phenyl-5-phenylpenta-2,4-dien-l-one (3), (2E,4E)-l-(4-nitro) phenyl-5-phenylpenta-2,4-dien- 1 -one (4), (2E,4E)- 1 -(2-methoxy)phenyl-5-phenylpenta- 2,4-dien-l-one (5), (2E,4E)-l-(3-methoxy)phenyl-5-phenylpenta-2,4-dien-l-one (6), (2E,4E)- 1 -(4-methoxy)phenyl-5-phenylpenta-2,4-dien- 1 -one (7), (2E,4E)- 1 -(2-methyl) phenyl-5-phenylpenta-2,4-dien-l-one (8), (2E,4E)-l-(3-metfiyl)phenyl-5-phenylpenta-2,4- dien-1-one (9) and (2E,4E)-l-(4-methyl)phenyl-5-phenylpenta-2,4-dien-l-one (10), were synthesized according to Claisen-Schmidt reaction. In the literature research, compounds 2, 8 and 9 were found to be new and compounds 1, 3, 4, 5, 7 and 10 were determined to be known. In the second part of the study, synthesized chalconoid like compound ((2E,4E)-1,5- diaril-2,4-pentadien-l-one) and its derivatives (1-10) were reacted by photochemical elecrrocyclic reaction to give cyclobutene containing 10 new chiral compounds (11-20). These compounds were named as; rel-cis-3-benzoil-4-phenyl-l -cyclobutene (11), rel-cis-3- (2-nitro)benzoil-4-phenyl- 1 -cyclobutene (12), rel-cis-3-(3 -nitro)benzoil-4-phenyl- 1 - cyclobutene (13), rel-cis-3-(4-nitro)benzoil-4-phenyl-l -cyclobutene (14), rel-cis-3-(2- methoxy)benzoil-4-phenyl- 1 -cyclobutene (15), rel-cis-3-(3 -methoxy)benzoil-4-phenyl- 1 - cyclobutene (16), rel-cis-3-(4-methoxy)benzoil-4-phenyl-l -cyclobutene (17), rel-cis-3-(2- methyl)benzoil-4-phenyl- 1 -cyclobutene (18), rel-cis-3-(3-methy)benzoil-4-phenyl- 1 - cyclobutene (19) and rel-cis-3-(4-methyl)benzoil-4-phenyl-l -cyclobutene (20). The structures of the synthesized compounds were identified by NMR, FT-IR, UV and LC- MS/MS techniques. Keywords: Chalconoids, Dihydrochalcone, Chiral, Cyclobutene, NMR, LC-MS/MS.