SYNTHESIS OF QUINOLINE-2(1H)-ONE AND QUINOLIN-4-CARBOXILIC ACID DERIVATIVES

• Main Author: Dianhar, Hanhan
• Format: Dissertations
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/32874
• Institution: Institut Teknologi Bandung

Quinoline is one of organic compounds which has been studied over years. This type of compound was commonly found in natural resources and has been widely observed for their advantages in human life. Quinolin-2(1H)-ones is one of quinoline derivatives which has been oxygenated at C2. This compound was found analogous to quinolin-4(1H)-ones, building block of commercial antibiotic class fluoroquinolones like cyprofloxacin (18) and levofloxacin (20). Some of quinolin2(1H)-one compounds which have been synthesized were 4-hydroxyquinolin2(1H)-one derivatives. The compounds were reported to show important activities e. g. antifungal, antibacterial, antiplatelet, and antitumor. Besides biological activities, 4-hydroxyquinolin-2(1H)-one derivatives also known to be potential in application of electronic and optical devices, based on its novel optical properties. In contrast, 4-methylquinolin-2(1H)-one derivatives have not much studied. Therefore, this reseach ini was conducted to sinthesize 4-methyl-2(1H)-quinolone derivatives and study their antibacterial activities and dye performance in DSSCs. 7-amino-4-methyl-2(1H)-quinolone (6) has been obtained through thermal condensation between ethyl acetoacetate and m-phenylenediamine. Compound 6 then underwent further reactions: prenylation, acetylation, benzoylation, diazonium coupling with some simple aromatic compounds, and iodine substitution. Structure of isolated products were determined based on spectroscopic data, including UV, IR, NMR (1D and 2D), and MS. Diazonium coupling product of 6 was then determined for DSSCs performances, while other compounds were evaluated for their antibacterial activities. Synthesis of quinoline derivatives gave 14 compounds. Prenylation of 6 yielded 7((3-methylbut-2-en-1-yl)amino)quinolin2(1H)-one (7) and 4-methyl-7(bis-(3-methylbut-2-en-1-il)amino)quinolin-2(1H)-on (8). Acetyla- tion of 6 gave N-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)acetamide (9) while its benzoylation product was identified as N-(4-methyl-2-oxo-1,2dihydroquinolin-7-yl)benzamide (10). Moreover, diazonium coupling of 6 at C7 with phenol, resorcinol, aniline, and m-phenylenediammine yielded 7-((4hydroxyphenil) diazenyl)-4-methyl quinolin-2(1H)-one (11), 7-((2,5-di hydroxyphenil)diazenyl)-4-methylquinolin-2(1H)-one (12), 7-((4-aminophenyl) diazenyl)-4-methylquinolin -2(1H)-one (13), and 7-((2,5-diaminophenyl)diazenyl) 4-methylquinolin-2(1H)-one (14), respectively. Iodination of 6 through Sandmeyer reaction was performed to obtain 7-iodo-4-methylquinolin-2(1H)-one (15) and cerium amonium nitrate (CAN) catalyzed iodination to afford 7-amino-2-hydroxy8-iodo-4-methylquinolin (16). Later on, two quinolin-4-carboxilic acid synthesis was also succesfully conducted to give 2-methylquinolin-4-carboxilic acid (17) dan 2-phenyquinolin-4-carboxilic acid (18) through Pfitzinger reaction of isatin (83). Esterification of both quinolin-4-carboxilic acid derivatives has been performed but only (2-methoxyethyl) 2-phenylquinolin-4-carboxilate (19) can be yielded from 18. DSSCs performance of dye 11-14 showed poor conversion of light energy. But the overall cell eficiencies showing consistent phenomenon related to its structural relationship to DSSCs properties. Furthermore, antibacterial activity of 6-10 and 15-19 gave no inhibition zone. This result showed that those compounds were impotential to be candidate of antibacterial agent.