Sübstitüe 2-oksazolidinon türevlerinin sentezi
Synthesis of substitute 2-oxazolidinone derivatives
Yazar: BAYHAN KARABULUT
Danışman: PROF. DR. AHMET METE ; DOÇ. DR. CUMHUR KIRILMIŞ
İnönü Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı
Derece: Doktora, 2017
Konu: Kimya = Chemistry

Özet:
Bu çalışmada, literatürde daha önce sentezlenmediği belirlenen 3-ariloksi-1,2-propandioller ve sübstitüe 2-oksazolidinonların sentezi amaçlandı. 3-Ariloksi-1,2-propandioller, çeşitli fenoller ile 3-klor-1,2-propandiolün etkileştirilmesiyle sentezlendi. Elde edilen 3-ariloksi-1,2-propandioller  üre ile polialkilen glikol içerisinde reaksiyona sokularak 2-oksazolidinonlar elde edildi. Elde edilen bileşikler saflaştırılıp IR, 1H NMR ve 13C NMR gibi spektroskopik yöntemlerle yapıları aydınlatıldı ve erime noktaları belirlendi.Bu çalışmada sentezlenen 3-ariloksi-1,2-propandiollerin yapıları aşağıda verilmiştir.
 
R1		R2		R3		R4		R5
1) 		H		CH3		H		CH3		H
2)		H		CH3		CH3		H		H
3)		Br		H		Cl		H		H
4)		Cl		H		Br		H		H
5)		Cl		H		H		H		H
6)		H		Cl		H		H		H
7)		H		H		Cl		H		H
8)		Cl		Cl		H		H		H
9)		Cl		H		Cl		H		H
10)		H		H		Br		H		H
11)		H		H		OCH3		H		H
12) 		H		H		CH(CH3)2	H		H
13)		H		CH3		Cl		H		H
14)		H		C2H5		Cl		H		H
15)		H		H		OC2H5		H		H
16)		H		H		OCH2Ph	        H		H
17)		H		H		C(CH3)3	        H		H
18)		OCH3		H		H		H		H

Sentezlenen 2-oksazolidinonlar  aşağıda verilmiştir.
R1		R2		R3		R4		R5
1) 		H		CH3		H		CH3		H
2)		H		CH3		CH3		H		H
3)		Br		H		Cl		H		H
4)		Cl		H		Br		H		H
5)		Cl		H		H		H		H
6)		H		Cl		H		H		H
7)		H		H		Cl		H		H
8)		Cl		Cl		H		H		H
9)		Cl		H		Cl		H		H
10)		H		H		Br		H		H
11)		H		H		OCH3		H		H
12) 		H		H		CH(CH3)2	H		H
13)		H		CH3		Cl		H		H
14)		H		C2H5		Cl		H		H
15)		H		H		OC2H5		H		H
16)		H		H		OCH2Ph	        H		H
17)		H		H		C(CH3)3	        H		H
18)		OCH3		H		H		H		H

Abstract:
In this work, we aimed to synthesize 3-aryloxy-1,2-propanediols and substituted 2-oxazolidinones which were not previously synthesized in the literature. 3-Aryloxy-1,2-propanediols were synthesized by the reaction of various phenols with 3-chloro-1,2-propanediol. The obtained 3-aryloxy-1,2-propanediols and urea were reacted in polyalkylene glycol to give 2-oxazolidinones. The obtained compounds were purified and their work was elucidated by spectroscopic methods such as IR,  1H NMR and 13C NMR, and melting points were determined.
The structures of 3-aryloxy-1,2-propanediols synthesized in this work are given below.
R1		R2		R3		R4		R5
1) 		H		CH3		H		CH3		H
2)		H		CH3		CH3		H		H
3)		Br		H		Cl		H		H
4)		Cl		H		Br		H		H
5)		Cl		H		H		H		H
6)		H		Cl		H		H		H
7)		H		H		Cl		H		H
8)		Cl		Cl		H		H		H
9)		Cl		H		Cl		H		H
10)		H		H		Br		H		H
11)		H		H		OCH3		H		H
12) 		H		H		CH(CH3)2	H		H
13)		H		CH3		Cl		H		H
14)		H		C2H5		Cl		H		H
15)		H		H		OC2H5		H		H
16)		H		H		OCH2Ph	        H		H
17)		H		H		C(CH3)3	        H		H
18)		OCH3		H		H		H		H
The synthesized 2-oxazolidinones are given below.
R1		R2		R3		R4		R5
1) 		H		CH3		H		CH3		H
2)		H		CH3		CH3		H		H
3)		Br		H		Cl		H		H
4)		Cl		H		Br		H		H
5)		Cl		H		H		H		H
6)		H		Cl		H		H		H
7)		H		H		Cl		H		H
8)		Cl		Cl		H		H		H
9)		Cl		H		Cl		H		H
10)		H		H		Br		H		H
11)		H		H		OCH3		H		H
12) 		H		H		CH(CH3)2	H		H
13)		H		CH3		Cl		H		H
14)		H		C2H5		Cl		H		H
15)		H		H		OC2H5		H		H
16)		H		H		OCH2Ph	        H		H
17)		H		H		C(CH3)3	        H		H
18)		OCH3		H		H		H		H