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Paper | Special issue | Vol 90, No. 1, 2015, pp.540-562
Published online, 22nd July, 2014
DOI: 10.3987/COM-14-S(K)57
Mn(III)-Based Oxidative Cyclization of N-Aryl-3-oxobutanamides. Facile Synthesis and Transformation of Substituted Oxindoles

Nobutaka Kikue, Tetsuya Takahashi, 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

The oxidation of 3-oxo-N-phenylbutanamides 1 with manganese(III) acetate in ethanol afforded dimeric 3,3'-biindoline-2,2'-dione derivatives 3–5. A similar reaction of N,2-disubstituted N-aryl-3-oxobutanamides 6 in acetic acid produced 3-acetylindolin-2-ones 7 bearing various substituents in good to excellent yields. The acetylindolinones 7 were easily deacetylated by treatment using neutral alumina in diethyl ether. Both the acetylindolinones 7 and deacetylated indolinones 8 were transformed by reduction into the substituted 1H-indoles.