Yeni kalkon bileşiklerinin sentezi ve açil hidrazin türevleriyle reaksiyonları
Synthesis of new chalcone compounds and reactions of open hydrazine derivatives
Yazar: FUNDA ÖZDEMİR
Danışman: PROF. DR. İLHAN ÖZER İLHAN
Erciyes Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı / Organik Kimya Bilim Dalı
Derece: Yüksek Lisans, 2018
Konu: Kimya = Chemistry

Özet:
Bu çalışmada, bazı yeni kalkon türevi bileşiklerin sentezi, kalkon türevi bileşiklerin hidrazitlerle reaksiyonu ve elde edilen bileşiklerin 2,4-dinitrofenilhidrazin ile reaksiyonlarının araştırılması amaçlanmıştır. 
Bu araştırma on üç yeni bileşiğin sentezi ile sonuçlanmıştır. Öncelikle bu çalışmada başlangıç maddesi olarak kullandığımız benzalasetofenon(BAF) türevleri (I). BAF, (II). BAF, (III). BAF, (IV). BAF, (V). BAF, (VI). BAF bileşikleri sentezlenmiştir. Daha sonra BAF türevi bileşiklerinin çeşitli hidrazitlerle reaksiyonları yapılarak sırasıyla; 1-(5-(4-metoksifenil)-3-fenil-4,5-dihidro-1H-pirazol-1-il)ethan-1-on (FÖ-2), 1-(3-fenil-5-(p-tolil)-4,5-dihidro-1H-pirazol-1-il)ethan-1-on (FÖ-3), 1-(5-(4-metoksifenil)-3-(p-tolil)-4,5-dihidro-1H-pirazol-1-il)ethan-1-on (FÖ-4), 1-(3-(4-metoksifenil)-5-(p-tolil)-4,5-dihidro-1H-pirazol-1-il)ethan-1-on (FÖ-5), 1-(5-(4-metoksifenil)-3-(p-tolil)-4,5-dihidro-1H-pirazol-1-il)-2-fenilethan-1-on (FÖ-6), 1-(3,5-di-p-tolil-4,5-dihidro-1H-pirazol-1-il)-2-fenilethan-1-on (FÖ-7), 1-(3-(4-metoksifenil)-5-(p-tolil)-4,5-dihidro-1H-pirazol-1-il)-2-fenilethan-1-on (FÖ-8), 2-fenil-1-(3-fenil-5-(p-tolil)-4,5-dihidro-1H-pirazol-1-il)ethan-1-on (FÖ-9), 1-(3-fenil-5-(p-tolil)-4,5-dihidro-1H-pirazol-1-il)ethan-1-on (FÖ-10) bileşikleri sentez edilmiştir. Elde edilen bu bileşiklerden bir kısmının 2,4-dinitrofenilhidrazin ile reaksiyonları yapılarak sırasıyla; (E)-1-(1-(2-(2,4-dinitrofenil) hidrazon)etil)-5-(4-metoksifenil)-3-fenil-4,5-dihidro-1H-pirazol (FÖ-11), (E)-1-(1-(2-(2,4-dinitrofenil)hidrazon)etil)-3-fenil-5-(p-tolil)-4,5-dihidro-1H-pirazol (FÖ-12), (E)-1-(1-(2-(2,4-dinitrofenil)hidrazon)etil)-5-(4-metoksifenil)-3-(p-tolil)-4,5-dihidro-1H-pirazol (FÖ-13), (E)-1-(1-(2-(2,4-dinitrofenil)hidrazon)-2-feniletil)-3,5-di-p-tolil-4,5-dihidro-1H-pirazol (FÖ-14) bileşikleri sentezlendi. 
Sentez edilen bileşiklerin yapıları Elementel Analiz, Nükleer Manyetik Rezonans Spektroskopisi (NMR) ve Infrared (IR) spektroskopisi yardımıyla aydınlatılmıştır.
Ayrıca FÖ-2 bileşiğinin X-ışını kristal analizleri yapılarak yapısı aydınlatılmıştır. 

Anahtar Kelimeler: Hidrazit, Kalkon, Pirazol, Nükleofilik Katılma Reaksiyonları

Abstract:
In this study, the synthesis of certain novel chalcone derivative compounds, hydrazides reaction of the chalcone derivative compounds and the resulting compounds was investigated on reaction with 2,4-dinitrophenylhydrazine.
This research has resulted in the synthesis of thirteen new compounds. Firstly, we used benzalacetophenone (BAF) derivatives as starting material in this study. (I). BAF, (II). BAF, (III). BAF, (IV). BAF, (V). BAF, (VI). BAF compounds were synthesized. Then, the BAF derivative compounds were reacted with various hydrazides to give, respectively, 1-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one (FÖ-2), 1-(3-phenyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one(FÖ-3), 1-(5-(4-methoxyphenyl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one (FÖ-4), 1-(3-(4-methoxyphenyl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one (FÖ-5), 1-(5-(4-methoxyphenyl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-phenylethan-1-one (FÖ-6), 1-(3,5-di-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)-2-phenylethan-1-one(FÖ-7), 1-(3-(4-methoxyphenyl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-phenylethan-1-one (FÖ-8), 2-phenyl-1-(3-phenyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one (FÖ-9), 1-(3-phenyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one (FÖ-10) compound synthesized. Some of these obtained compounds were reacted with 2,4-dinitrophenylhydrazine, respectively; (E)-1-(1-(2-(2,4-dinitrophenyl) hydrazineylidene)ethyl)-5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole (FÖ-11), (E)-1-(1-(2-(2,4-dinitrophenyl)hydrazono)ethyl)-3-phenyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazole (FÖ-12), (E)-1-(1-(2-(2,4-dinitrophenyl)hydrazono)ethyl)-5-(4-methoxyphenyl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazole (FÖ-13), (E)-1-(1-(2-(2,4-dinitrophenyl) hydrazono)-2-phenylethyl)-3,5-di-p-tolyl-4,5-dihydro-1H-pyrazole (FÖ-14) compound synthesized.
The structures of the synthesized compounds were elucidated by Elemental Analysis, Nuclear Magnetic Resonance Spectroscopy (NMR) and Infrared (IR) spectroscopy.
Also X-ray crystal analysis of the FÖ-2 compound made is illuminated structure.

Keywords: Hydrazide, Chalcone, Pyrazole, Nucleophilic Addition