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Communication | Special issue | Vol 82, No. 2, 2010, pp.1157-1162
Published online, 22nd October, 2010
DOI: 10.3987/COM-10-S(E)110
Oxidation of Pyrrole-2-carboxylates with o-Chloranil and Its Synthetic Application

Ryo Sakata, Ryoji Iwamoto, Shuhei Fujinami, Yutaka Ukaji,* and Katsuhiko Inomata*

*Chemistry Course, College of Science and Engineering, School of Chemistry, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

t-Butyl 3,4-dialkyl-1H-pyrrole-2-carboxylates were oxidized with o-chloranil in the presence of MeOH to afford the corresponding 5-methoxypyrrolin-2-one derivatives. The resulting 5-methoxypyrrolin-2-one was reacted with various nucleophiles under acidic conditions to afford the functionalized pyrrolinone derivatives in good yields.