Koji Yamada, T. Izumi, F. Yamada
Dec 31, 2005
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Journal
Heterocycles
Abstract
l-Methoxy-3-(2-nitrovinyl)indole (la) 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 la, 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 la at the 2-position predominantly with concomitant liberation of the 1-methoxy group giving 2-substituted indoles.