Jumina Jumina(1*)

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


1-Phenacyl-3-aryl-4,6-dimethoxyindoles 2b and 2c were obtained in good yields respectively through cyclization of N,N-diphenacylaniline 1b and 1c in trifluoroacetic acid. However, instead of giving pyrroloindole 3c, treatment of phenacylindole 2c with polyphosphoric acid afforded indolizine 5 in 42% yield. Phenacylindole 2c reacts with the Vilsmeier aroylation reagent consisted of a mixture of phosphoryl chloride and p-chloro-N,N-dimethylbenzamide to give 2-aroylindole 6 (32%) and pyrroloindole 7 (22%). When treated with sodium borohydride, phenacylindole 2c gave alcohol 8 in 83% yield. Nonetheless, treatment of alcohol 8 with either p-toluenesulfonic acid in glacial acetic acid or boron trifluoride etherate in benzene did not give the desired dihydropyrroloindole 12. Instead, the reactions afforded respectively acetyl ester 9 and indole 10 in 56% and 63% yield.


phenacylindole; aroylindole; pyrroloindole; indolizine

Full Text:

Full Text PDF


[1] Bartsch, H., 1976, Monatsh. Chem., 107, 663- 667

[2] Bartsch, H., 1981, Monatsh. Chem., 112, 1451-1457

[3] Keller, P.A., Ph.D Thesis, 1991, University of New South Wales, Sydney, Australia

[4] Black, D.StC., Gatehouse, B.M.K.C., Theobald, F., and Wong, L.C.H., 1980, Aust. J. Chem., 33, 343-350

[5] Still, W.C., Kahn, M., and Mitra, A., 1978, J. Org. Chem., 43, 2923-2925

[6] Crowther, A.F., Mann, F.G., and Purdie, D., 1943, J. Chem. Soc., 58-68

[7] Black, D.StC,, Bowyer, M.C., Bowyer, P.K., Ivory, A.J., Kim, M., Kumar, N., McConnell, D.B., and Popiolek, M., 1994, Aust. J. Chem., 47, 1741-1750


Article Metrics

Abstract views : 1021 | views : 1088

Copyright (c) 2010 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Analytics View The Statistics of Indones. J. Chem.