SYNTHESIS OF NOVEL INDOLO[3,2-c]QUINOLINES; ETHYL 3-CHLORO-9,11-DIMETHOXY INDOLO[3,2-c]QUINOLINE-6-CARBOXYLATE

https://doi.org/10.22146/ijc.21786

Tutik Dwi Wahyuningsih(1*)

(1) Chemistry Department, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Yogyakarta 55281
(*) Corresponding Author

Abstract


β-Carboline and its derivatives are significant due to their pharmacological importance. The synthesis of indolo[3,2-c]quinolines as a benzo analog of β-carboline has been carried out via an oxime ether intermediate. Reaction of 2'-glyoxylic ester with hydroxylamine hydrochloride in the presence of sodium acetate afforded the oxime acetate in 82%. It was then treated with natrium and fluoro-2,4-dinitrobenzene in ethanol to give an orange solid of oxime ether acetate which is in subsequent treatment with a base yielded a pale yellow solid of indolo[3,2-c]carboline in 43%.


Keywords


β-carboline; oxime; indolo[3,2-c]quinoline

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References

[1] Ishida, J., Wang, H.K., Oyama, M., Cosentino, M.L., Hu, C.Q. and Lee, H.H., 2001, J. Nat. Prod., 64, 958-960.

[2] Fryer, R.I., Ning, R.Y.F., Sternbach, L.H. and Walser, A. U.S.patent 1977, 4014883.

[3] Jeevanandam, A. and Srinivasan, P.C., 1995, Synth. Commun., 25, 3427-3434.

[4] Jones, A.W., 2000, Investigation into indole synthesis, manipulation and macrocyclisation, Ph.D Thesis, University of New South Wales.

[5] Uchiyama, K., Hayashi, Y. and Narasaka, K., 1997, Synlett, 445-446.

[6] Uchiyama, K., Ono, A., Hayashi, Y. and Narasaka, K., 1998, Bull. Chem. Soc. Jpn., 71, 2945-2955.

[7] Ono, A. and Narasaka, K., 2001, Chem. Lett., 146-147.

[8] Cho, B.R., Park, C.W. and Je, J.T., 1995, J. Chem. Res. Synop., 200-201.



DOI: https://doi.org/10.22146/ijc.21786

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