Research ArticleOpen AccessGoogle Scholar indexed
A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-<i>b</i>]quinolin-13(6<i>H</i>)-one and Its Derivatives
Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, China
Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, China
Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, China
Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, China
- 1 Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, China
- 2 Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, China
- 3 Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, China
- 4 Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, China
International Journal of Organic Chemistry·Volume 03 (2013)·Pages 119–124·Published 13 June 2013·DOI10.4236/ijoc.2013.32013
Copy link · social · email
Abstract
A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4- b ]quinolin13(6 H )-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.
KeywordsThe Intramolecular Friedel-Crafts Acylation Reaction: 910-Dimethoxybenzo[67]oxepino[34-<i>b</i>]quinolin-13(6<i>H</i>)-one and Its Derivatives67-Dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic Acid: Ethyl67-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylate: PPA
- R. D. Larsen, E. G. Corley, A. O. King, J. D. Carrol, P. Davis, T. R.Verhoeven, P. J. Reider, M. Labelle, J. Y. Gauthier, Y. B. Xiang and R. J. Zamboni, “Practical Route to a New Class of LTD4 Receptor Antagonists,” Journal of Organic Chemistry, Vol. 61, No. 10, 1996, pp. 3398-3405. doi:10.1021/jo952103j
- Y. L. Chen, K. C. Fang, J. Y. Sheu, S. L. Hsu and C. C. Tzeng, “Synthesis and Antibacterial Evaluation of Certain Quinolone Derivatives,” Journal of Medicinal Chemistry, Vol. 44, No. 14, 2001, pp. 2374-2377. doi:10.1021/jm0100335
- J. P. Michael, “Quinoline, quinazoline and acridone alkaloids,” Natural Product Reports, Vol. 15, No. 6, 1998, pp. 595-606. doi:10.1039/a815595y
- M. E. Zwaagstra, H. Timmerman, A. C. Van De Stolpe, F. J. De Kanter, M. Tamura, Y. Wada and M. Q. Zhang, “Synthesis and Structure-Activity relatIonships of Carboxyflavones as Structurally Rigid CysLT1 (LTD4) Receptor Antagonists,” Journal of Medicinal Chemistry, Vol. 41, No. 9, 1998, pp. 1428-1438. doi:10.1021/jm970179x
- A. Von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Wiestner, G. P. Anderson, U. Niederhauser, N. Subramanian and M. A. Bray, “Synthesis and SAR of a Novel, Potent and Structurally Simple LTD4 Antagonist of the Quinoline Class,” Bioorganic & Medicinal Chemistry Letters, Vol. 8, No. 8, 1998, pp. 965-970. doi:10.1016/S0960-894X(98)00137-1
- D. Doub`e, M. Blouin, C. Brideau. C. Chan, S. Desmarais, D. Ethier, J. P. Falgueyret, R. W. Friesen, M. Girard, Y. Girard, J. Guay, P. Tagari and R. N. Young, “Quinolines as Potent 5-Lipoxygenase Inhibitors: Synthesis and Biological Profile of L-746,530,” Bioorganic & Medicinal Chemistry Letters, Vol. 8, No. 10, 1998, pp. 1255-1260. doi:10.1016/S0960-894X(98)00201-7
- B. Vaitilingam, A. Nayyar, P. B. Palde, V. Monga, R. Jain, S. Kaur and P. P. Singh, “Synthesis and Antimyco-bacterial Activities of Ring-Substituted Quinolinecarboxylic Acid/Ester Analogues. Part 1,” Bioorganic & Medicinal Chemistry, Vol. 12, No. 15, 2004, pp. 4179-4188. doi:10.1016/j.bmc.2004.05.018
- Y. L. Chen, K. C. Fang, J. Y. Sheu, S. L. Hsu and C. C. Tzeng, “Synthesis and Antibacterial Evaluation of Certain Quinolone Derivatives,” Journal of Medicinal Chemistry, Vol. 44, No. 14, 2001, pp. 2374-2377. doi:10.1021/jm0100335
- G. Roma, M. D. Braccio, G. Grossi, F. Mattioli and M. Ghia, “1,8-Naphthyridines IV. 9-Substituted N, N-Dialkyl -5-(Alkylamino or Cycloalkylamino) [1,2,4]Triazolo[4,3-a][1,8]naphthyridine-6-carboxamides, New Compounds with Anti-Aggressive and Potent Anti-Inflammatory Activities,” European Journal of Medicinal Chemistry, Vol. 35, No. 11, 2000, pp. 1021-1035. doi:10.1016/S0223-5234(00)01175-2