Iodination of 4,6-Dimethoxyindole Derivatives
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Abstract
In this research, the iodination of 4,6-dimethoxyindole derivatives with N-iodosuccinimide in dichloromethane at 0 oC and room temperature were studies. The iodination of 4,6-dimethoxy-2,3-diphenylindole without substituents at C5 and C7 position and 3-(4-bromophenyl)-4,6-dimethoxyindole without substituents at C2, C5 and C7 position gave 7-iodoindole derivatives which is substited product with iodine atom at C7 position. In the case of iodination of 7-formyl-4,6-dimethoxy-2,3-diphenylindole without substituents at C5 was not found 5-iodoindole product. Moreover, the iodination of 4,6-dimethoxyindole without substituents at C2, C3, C5 and C7 was not found iodoindole product. Finally, the results of selective substitution products of iodination are similar to chlorinations and brominations but the chemical yield of iodination products are less than those of chlorination and bromination products.
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References
Adams, S.E., Parr, C., Miller D.J., Allemann, R.K. and Hallett, M.B. (2012). Potent inhibition of Ca2+-dependent activation of Calpain-1 by Novel Mercaptoacrylate. Medicinal Chemistry Communications, 3, 566-570.
Black, D.St.C. (1993). New dimensions in indole chemistry: From ligand design to natural product. Synlett, 4, 246-252.
Black, D.St.C., Bowyer, M.C., Kumar, N. and Mitchell, P.S.R. (1993). Calix[3]indoles, new macrocyclic Tris(indolylmethylene) compounds with 2,7-linkages. Journal of Chemical Society, Chemical Communication, 10, 819-821.
Black, D.St.C., Bowyer, M.C., Catalano, M.M., Ivory, A.J., Keller, P.A., Kumar, N. and Nugent, S.J. (1994). Substitution, oxidation and addition reactions at C-7 of activated Indoles. Tetrahedron, 50, 10497-10508.
Black, D.St.C., Kumar, N. and Mitchell, P.S.R. (2002). Synthesis of pyrroloquinolines as indole analogues of flavonols. Journal of Organic Chemistry, 67, 2464-2473.
Hamri, S., Rodriguez, J., Basset, J., Guillaumet, G. and Pujol, M.D. (2012). A convenient iodination of indoles and derivatives. Tetrahedron, 68, 6269-6275.
Hesse, M. (2002). Alkaloids nature’s curse or blessing?. Zürich: Wiley-VCH.
Keawin, T. (2005). Synthesis of endoperoxide of anthracene derivatives and their biological activities and chemistry of 4,6-dimethoxyindole derivatives photooxidation and nitration. Doctoral Dissertation. Bangkok: Mahidol University.
Keawin, T., Kotchapradist, P., Promarak, V., Saengsuwan, S., Sudyoadsuk, T. and Jungsuttiwong, S. (2011). Selective bromination of 4,6-dimethoxyindole derivatives. Journal of Science and Technology, Ubon Ratchathani University, 13, 24-32.
Keawin, T. and Sirithip, K. (2016). Chlorination of 4,6-dimethoxyindole derivatives. Journal of Science and Technology, Ubon Ratchathani University, 18, 39-49.
Marsch, N., Jones, P.G. and Lindel, T. (2015). SmI2-mediated dimerization of indolylbutenones and synthesis of the myxobacterial natural product indiacen B. Beilstein Journal of Organic Chemistry, 11, 1700–1706.
Rajasekharan, S.K., Kim, S., Kim, J.C. and Lee, J. (2020). Nematicidal Activity of 5-iodoindole against root-knot nematodes. Pesticide Biochemistry and Physiology, 163, 76-83.
Tidwell, J.H., Peat, A.J. and Buchwald, S.L. (1994). Synthesis and reactions of 3-(bromomethyl)-1-carbethoxy-4-iodoindole: The preparation of 3,4-differentially substituted indoles. Journal of Organic Chemistry, 59, 7164-7168.
Wu, Y.S., Coumar, M.S., Chang, J.Y., Sun, H.Y., Kuo, F.M., Kuo, C.C., Chen, Y.J., Chang, C.Y., Hsiao, C.L., Liou, J.P., Chen, C.P., Yao, H.T., Chiang, Y.K., Tan, U.K., Chen, C.T., Chu, C.Y., Wu, S.Y., Yeh, T.K., Lin, C.Y. and Hsieh, H.P. (2009). Synthesis and evaluation of 3-aroylindoles as anticancer agents: metabolite approach. Journal of Medicinal Chemistry, 52, 4941-4945.
Zhang, Q., Peng, Y., Wang, X.I., Keenan, S.M., Arora, S. and Welsh, W.J. (2007). Highly potent triazole-based tubulin polymerization inhibitors. Journal of Medicinal Chemistry, 50, 749-754.
