Synthesis of 4-alkoxy-8-hydroxyquinolines

Journal of Organic Chemistry

Volumn 72, Issue 3, 2007, Pages 920-922

  Heiskanen, Juha P ^a   Omar, Walaa A E ^a   Ylikunnari, Mari K ^a   Haavisto, Kirsi M ^a   Juan, Maria J ^a   Hormi, Osmo E O ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CARBON; HYDROLYSIS; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

4-ALKOXY-8-HYDROXYQUINOLINES; SODIUM HYDRIDE; TOSYL GROUP;

NITROGEN COMPOUNDS;

8 QUINOLINOL DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33846937838     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062175i     Document Type: Article

References (17)

1. Novak, I.; Kovac, B. J. Org. Chem. 2004, 69, 5005.
2. Sawada, Y.; Kayakiri, H.; Abe, Y.; Mizutani, T.; Inamura, N.; Asano, M.; Hatori, C.; Aramori, I.; Oku, T.; Tanaka, H. J. Med. Chem. 2004, 47, 2853.
3. (a) Pierre, J.; Baret, P.; Serratrice, G. Curr. Med. Chem. 2003, 10, 1077.
4. (b) Mossialos, D.; Meyer, J. M.; Budzikiewicz, H.; Wolff, U.; Koedam, N.; Baysse, C.; Anjaiah, V.; Cornelis, P. Appl. Environ. Microbiol. 2000, 66, 487.
5. Tang, C. W.; Van Slyke, S. A. Appl. Phys. Lett. 1987, 51, 913.
6. Curioni, A.; Andreoni, W. IBM J. Res. Dev. 2001, 45, 101.
7. Dempcy, R. O.; Kutyavin, I. V.; Mills, A. G.; Lukhtanov, E. A.; Meyer, R. B. Nucleic Acids Res. 1999, 27, 2931.
8. Synthetic procedure to produce other 4-position-substituted 8-tosyl-oxyquinoline, and its derivatives will be published during our future work.
9. Our initial route to prepare 2 involved the use of the Gould-Jacobs reaction of substituted anilines with diethyl ethoxymethylenemalonate. Unfortunately, cyclization led to less than 30% yield, and all attempts to improve the yield were unsuccesful. For a review of Gould-Jacobs reaction, see: Gould, R. G.; Jacobs, W. A. J. Am. Chem. Soc. 1939, 61, 2890.
10. (a) Morita, J.-I.; Nakatsuji, H.; Misaki, T.; Tanabe, Y. Green Chem. 2005, 7, 711.
11. (b) Ouchi, M.; Inoue, Y.; Liu, Y.; Nagamune, S.; Nakamura, S.; Wada, K.; Hakushi, T. Bull. Chem. Soc. Jpn. 1990, 63, 1260.
12. Our initial effort to alkylate tosylated quinoline 3 involved the use of potassium carbonate, potassium iodide, and alkyl halide according to the general method of the Claisen O-alkylation. With that method, alkylation products 4b,d were obtained in moderate yields.
13. An opposite effect of solvents is seen in alkylation of 2-pyridone: Hopkins, G. C.; Jonak, J. P.; Minnemeyer, H. J.; Tieckelmann, H. J. Org. Chem. 1967, 32, 4040.
14. Grandjean, D.; Dhimane, H.; Pommelet, J.-C.; Chuche, J. Bull. Soc. Chim. Fr. 1989, 5, 657 reports a melting point of 197°C;
15. however, the melting point differs strongly from our melting point, 320°C, which is much closer to the melting point of 2,4-dihydroxyquinoline, 355°C: CRC Handbook of Chemistry and Physics, 62nd ed.; Weast, R. C., Ed.; CRC Press Inc.: Boca Raton, FL, 1982.
16. Silica gel with 0.040-0.063 mm particle size was used as a support in every flash chromatography purification procedures.
17. In other hydrolysis reactions ethanol was used instead of methanol to help dissolution.