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Communication | Regular issue | Vol 29, No. 4, 1989, pp.643-648
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4863
New Reactions of Thallium Compounds: A Simple Synthesis of 4- and 7-Substituted Indoles Bearing a Nitro or an Azido Group

Masanori Somei,* Fumio Yamada, Hirokazu Hamada, and Toshio Kawasaki

*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

New reactions for converting thallium compounds to nitro and azido compounds are elaborated. Applying these reactions, 4-nitroindole-3-carboxaldehyde and 1-acetyl-2,3-dihydro-7-nitroindole are now readily available in one pot reaction from indole-3-carboxaldehyde and 1-acetyl-2,3-dihydroindole, respectively. 4-Azidoindole-3-carboxaldehyde and 1-acetyl-7-azido-2,3-dihydroindole are similarly produced. Preparation of methyl 4-nitroindole-3-carboxylate is also reported.