An Efficient One-Pot Three-Component Synthesis of Novel Quinazoline-4-Carboxylic Acid and Its Ester and Amide Derivatives

Yıl 2022, Cilt: 50 Sayı: 4, 377 - 386, 09.10.2022

Derviş Gök

https://doi.org/10.15671/hjbc.1004758

Öz

A series of novel quinazoline derivatives, which may be drug candidates, were synthesized, and their structures were characterized by IR, 1H NMR, 13C NMR and Q-TOF LC/MS spectrometry. First, 2-(4-chloro-phenyl)-quinazoline-4-carboxylic acid (2) was synthesized from a one-pot three-component condensation reaction of (2-amino-phenyl)-oxo-acetic acid sodium salt obtained from alkaline hydrolysis of isatin (indole-2,3-dione) with 4-chlorobenzaldehyde and ammonium acetate. The carboxylic acid compound 2 allowed the synthesis of the ester, acid chloride and amide derivatives. New quinazoline ester derivatives (3-6, 8) were synthesized by the reactions of compound 2 and various alcohols. Quinazoline amide derivatives (9-13) were then obtained from the reaction of different aliphatic and aromatic amines and 2-(4-chloro-phenyl)-quinazoline-4-carbonyl chloride (7) formed from the reaction of SOCl2 and compound 2.

Anahtar Kelimeler

Isatin, quinazoline-4-carboxylic acid, amide, ester

Destekleyen Kurum

Kütahya Dumlupınar University Technology Research Fund

Proje Numarası

No, 2015/24

Teşekkür

The author thank the Kütahya Dumlupınar University Technology Research Fund for supporting this study with a scientific research project (No, 2015/24).

Bir Etkili Tek Ortamda Üç Bileşenli Yeni Kinazolin-4-Karboksilik Asit ve Onun Ester ve Amit Türevlerinin Sentezi

Öz

İlaç adayları olabilecek bir dizi yeni kinazolin türevleri sentezlendi ve yapıları IR, 1H NMR, 13C NMR ve Q-TOF LC/MS spektrometresi ile karakterize edildi. Önce amonyum asetat ve 4-klorobenzaldehit ile isatinin (indol-2,3-dion) hidrolizinden elde edilen (2-amino-fenil)-okso-asetik asit sodyum tuzunun aynı ortamda üç bileşenli kondenzasyon reaksiyonundan 2-(4-kloro-fenil)-kinazolin-4-karboksilik asit (2) sentezlendi. Karboksilik asit bileşiği 2, ester, asit klorür ve amit türevlerinin sentezine izin verdi. Yeni kinazolin ester türevleri (3-6, 8), 2 bileşiği ve çeşitli alkollerin reaksiyonlarından sentezlendi. Daha sonra kinazolin amit türevleri (9-13), çeşitli alifatik ve aromatik aminlerin 2 bileşiği ve SOCl2’ün reaksiyonundan oluşan 2-(4-kloro-fenil)-kinazolin-4-karbonil klorürün (7) reaksiyonundan elde edildi.

Anahtar Kelimeler

İsatin, kinazolin-4-karboksilik asit, amit, ester

Proje Numarası

No, 2015/24

Kaynakça

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