SYNTHESIS OF QUINOLINONE AND ITS DERIVATIVES

• Main Author: MARCO RUMENGAN ( NIM : 20514048 ), STEFAN
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/24373
• Institution: Institut Teknologi Bandung

Quinolinone is a quinoline derivative of heterocyclic compounds which have structural similarities with coumarin. In this research, synthesis of quinolinone structures have been done. Reaction products obtained were characterized by NMR spectroscopy and Mass spectrometry. Compound 1 (7-amino-4-methyl-2- quinolinone) is the quinolinone basic structure in this study is shown by &#948;H 11.22 ppm as quinolinone spesific signal. Compound 2 (7-amino-8-iodo-4-methyl-2- quinolinone) is the result of iodonation that shown at m/z 300.9839 and there is no longer a multiplicity of double doublet. Compound 2 can be used as precursor in C- C coupling reaction. Compound 1 can be transformed into various diazo quinolinone derivates, one of them is coupling with resorcinol. Compound 3 is 7- [(2,4-dihidroxylphenyl)diazenyl]-4-methyl-2-quinolinone. Compound 3 is the result of diazo coupling with resorcinol. Compound 3 is characterized by UV-Vis and FTIR and shown that there is diazo coupling (&#955;max = 434 nm; &#957; =1421 cm-1 and <br /> <br /> <br /> <br /> 1473 cm-1) with N=N bond. The addition of various metal ions gave hypsochromic shift toward &#955;max value of diazo. The alkaline earth and transition metal ion complexes gave hypsochromic shift more than alkaline ion complexes.(rums) (gambar)Reagent : a. AcAcOEt (1 eq), 120oC, 18 h (40%); b. ICl (1 eq), AcOH, RT, 2 h, (37%); c. (1) NaNO2 (1 eq), HCl-AcOH-H2O, 0-5 oC, 1 h (2) Resorcinol (1 eq), MeOH-Xylene, NaOAc-NaOH, -5 oC, 12 h (29%). <br />