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Paper | Regular issue | Vol 71, No. 11, 2007, pp.2457-2463
Published online, 3rd August, 2007
DOI: 10.3987/COM-07-11145
Nitration of Dimethyl 1-Substituted Indole-2,3-dicarboxylates: Synthesis of Nitro- and Aminoindole Derivatives

Yasuyoshi Miki,* Misako Umemoto, Hiroko Maruyama, Makoto Kuromatsu, and Hiromi Hamamoto

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan

Abstract

The treatment of dimethyl indole-2,3-dicarboxylate with nitronium tetrafluoroborate in the presence of tin (IV) chloride produced dimethyl 5 nitroindole-2,3-dicarboxylate as the major product. In a similar manner, the dimethyl 1 benzyl- and 1-benzenesulfonylindole-2,3-dicarboxylates provided a mixture of the corresponding 4-nitro-, 5 nitro-, 6-nitro- and 7-nitroindole derivatives. However, dimethyl 5-bromoindole-2,3- dicarboxylate gave dimethyl 5-bromo-4-nitroindole-2,3-dicarboxylate as the sole product, which was converted to dimethyl 4-aminoindole-2,3-dicarboxylate.