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Paper | Special issue | Vol 97, No. 1, 2018, pp.431-450
Published online, 31st May, 2018
DOI: 10.3987/COM-18-S(T)31
Facile Synthesis of Indolelactones Using Mn(III)-Based Oxidative Substitution-Cyclization Reaction

Takeshi Inoue and Hiroshi Nishino*

*Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami 2-39-1, Chûou-Ku, Kumamoto 860-8555, Japan

Abstract

Based on the oxidation of indole with Mn(OAc)3 in the presence of 1,1-diarylethenes affording 3-vinyl-substituted indoles, a similar oxidation using indole-2-carboxylic acids was evaluated in order to effectively introduce the substituent group to the C-3 position of the indolecarboxylic acids. The coupling reaction followed by oxidative cyclization smoothly proceeded at room temperature in an AcOH-HCO2H mixed solvent to give the desired indolelactones in high yields. The reaction details, the structure determination of the products and a brief reaction mechanism are described.