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Note | Special issue | Vol 66, No. 1, 2005, pp.583-594
Published online, 18th October, 2005
DOI: 10.3987/COM-05-S(K)33
Solvent Effect on the Reaction of 1-Methoxy-3-(2-nitrovinyl)indole with Nucleophiles

Koji Yamada, Tomoyuki Izumi, Fumio Yamada, and Masanori Somei*

*Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

1-Methoxy-3-(2-nitrovinyl)indole (1a) functions as an electrophile and reacts with various nucleophiles. In THF, nucleophiles undergo conjugate addition to the β-carbon of the nitrovinyl side chain of 1a, regioselectively. The resultant Michael addition products (4d and 8) cyclize to novel 3-substituted 1-methoxyindoles (5 and 7) depending on reaction conditions and a plausible mechanism is discussed. In dipolar aprotic solvent (DMF), nucleophiles react with 1a at the 2-position predominantly with concomitant liberation of the 1-methoxy group giving 2-substituted indoles.