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Paper | Regular issue | Vol 65, No. 10, 2005, pp.2381-2394
Published online, 12th August, 2005
DOI: 10.3987/COM-05-10487
Manganese(III) Acetate Mediated Oxidative Free Radical Reactions between Indole Derivatives and 1,3-Dicarbonyl Compounds

An-I Tsai, Chia-Hui Lin, and Che-Ping Chuang*

*Department of Chemistry, National Cheng Kung University, 1, Ta-Shiueh Rd., Tainan, 70101, Taiwan, R.O.C.

Abstract

Manganese(III) mediated oxidative free radical reactions between indole derivatives and 1,3-dicarbonyl compounds are described. In the presence of dimethyl malonate, the oxidative free radical reaction of 3-unsubstituted indoles resulted in the formation of 2-(3-oxo-2-indolylidene)malonates and these malonates can be prepared in much better yields from corresponding 3-indolecarboxylic acids. On the contrary, the oxidative free radical reaction between 3-unsubstituted indoles and 2,4-pentanedione or ethyl acetoacetate gave furo[3,2-b]indoles.