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Communication | Special issue | Vol 86, No. 2, 2012, pp.1031-1038
Published online, 22nd November, 2012
DOI: 10.3987/COM-12-S(N)126
DIRECT OXIDATION OF 4-METHYLPYRROLE-2-CARBOXYLATES WITH DDQ IN THE PRESENCE OF A GLYCOL

Kana Takahashi, Ryoji Iwamoto, Ryo Sakata, Takahiro Soeta, Katsuhiko Inomata, and Yutaka Ukaji*

*Chemistry Course, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

Oxidation of 4-methylpyrrole-2-carboxylates with DDQ in the presence of a glycol proceeded smoothly on the methyl group at the C4 position regioselectively to afford the corresponding pyrrole-2,4-dicarboxylates directly. Direct oxidation of a methyl group of 2,4,6-trimethylphenol and 3-methyl-9H-carbazole into carboxylates was also demonstrated.