ALDOL CONDENSATION OF N-ALKYLATED-3-ARYL-4,6-DIMETHOXY-7-FORMYLINDOLES AS A GOOD METHOD FOR THE SYNTHESIS OF 1-ARYL-6,8-DIMETHOXYPYRROLO[3,2,1-hi]INDOLE-4-CARBOXYLATES
Jumina Jumina(1*)
(1) Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281
(*) Corresponding Author
Abstract
Alkylation of 3-aryl-4,6-dimethoxyindole 3a and 3b with methyl and ethyl a-bromoacetates afforded good yields of indol-1-ylacetates 4. Treatment of these indoles 4 with the Vilsmeier formylation reagent gave formylindoles 5 in 54-81 % yield. These formylindole 5 underwent intramolecular aldol condensation when treated with sodium hydride in tetrahydrofuran to give pyrroloindole-4-carboxylates 6 in 30-60 % yield. Structural assignment based on spectroscopic data confirmed the structure of the synthesized pyrroloindoles. In the case of pyrroloindole 6c, the structure of this molecule was also proven by X-ray crystallography data.
Keywords
Full Text:
Full Text PdfReferences
[1] Pomeroy, A.R., and Raper, C., 1971, Eur. J. Pharmacol., 14, 374-383.
[2] Lathbury, D.C., Parsons, P.J., and Pinto, I., 1988, J. Chem. Soc., Chem. Commun., 81-82.
[3] Anet, F.A.L., Muchowski, J.M., and Nishizawa, E., 1961, Chem. & Ind. (London), 1117.
[4] Robinson, B., 1963, Chem. Rev., 63, 373-401.
[5] Robinson, B., 1968, Chem. Rev., 68, 227-250.
[6] Van Order, R.B., and Lindwall, H.G., 1941, Chem. Rev., 41, 69-96.
[7] Paudler, W.W., and Shin, H.G., 1969, J. Heterocycl. Chem., 6, 415-417.
[8] Ishii, H., Takeda, H., Hagiwara, T., Sakamoto, M., and Kogusuri, K., 1989, J. Chem. Soc. Perkin Trans. 1, 2407-2414.
[9] Brown, D.W., Mahon, M.F., Ninan, A., Sainsbury, M., and Shertzer, H.G., 1993, Tetrahedron, 49, 8919-8932.
[10] Bartsch, H., 1976, Monatsh. Chem., 107, 663-667.
[11] Bartsch, H., 1981, Monatsh. Chem., 112, 1451-1457.
[12] Keller, P.A., 1991, Ph.D Thesis, University of New South Wales,.
[13] Still, W.C., Kahn, M., and Mitra, A., 1978, J. Org. Chem., 43, 2923-2925.
[14] 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.
[15] Black, D.StC., Keller, P.A., and Kumar, N., 1993, Aust. J. Chem., 46, 843-862.
[16] Heaney, H., and Ley, S.V., 1973, J. Chem. Soc. Perkin Trans. I, 499-500.
[17] Seshadri, S., 1973, J. Scient. Ind. Res., 32, 128-149.
[18] Marson, C.M., 1992, Tetrahedron, 48, 3659-3726.
[19] Meth-Cohn, O., and Stanforth, S.P, 1991, Comprehensive Organic Chemistry, Vol. 2, Trost, B.M. Fleming, I., Chief Ed. Heathcock, C.H., Vol. Ed., Pergamon Press, Oxford, p.777-794.
[20] Meth-Cohn, O., and Tarnowski, B., 1982, Adv. Heterocycl. Chem., 31, 207-236.
[21] Joule, J.A., and Smith, G.F., 1978, Heterocyclic Chemistry, Van Nostrand Reinhold (International), Second edition, Great Britain, p. 279-283.
[22] Brown, V.H., Skinner, W.A., and De Graw, J.I. 1969, J. Heterocycl. Chem., 6, 539-543.
[23] Carlsson, A., Carrodi, H., and Magnusson, T., 1963, Helv. Chim. Acta, 46, 1231-1235.
[24] Black, D.StC., Kumar, N., and Wong, L.C.H., 1986, Synthesis, 474-476.
[25] Black, D.StC. Bowyer, M.C., Kumar, N., and Mitchell, P.S.R., 1993, J. Chem. Soc., Chem. Commun., 819-821.
DOI: https://doi.org/10.22146/ijc.21735
Article Metrics
Abstract views : 1646 | views : 1561Copyright (c) 2010 Indonesian Journal of Chemistry
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.
View The Statistics of Indones. J. Chem.