Unexpected Formation of Quinolone Derivatives in Reissert Indole Synthesis

Hideharu Suzuki; Hiroshi Gyoutoku; Hiroe Yokoo; Mika Shinba; Yuka Sato; Hiroshi Yamada; Yasuoki Murakami

doi:10.1055/s-2000-6758

Synlett 2000; 2000(8): 1196-1198
DOI: 10.1055/s-2000-6758

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Unexpected Formation of Quinolone Derivatives in Reissert Indole Synthesis

Hideharu Suzuki^* , Hiroshi Gyoutoku, Hiroe Yokoo, Mika Shinba, Yuka Sato, Hiroshi Yamada, Yasuoki Murakami

^*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan; Fax + 81 4 74 72 15 95; E-mail: murakami@phar.toho-u.ac.jp

Abstract

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The Reissert indole synthesis was found to unexpectedly give 3-hydroxy-1,2,3,4-tetrahydro-2-quinolone derivative 4, sometimes in a high ratio with the expected ethyl indole-2-carboxylate derivatives 3 in a low ratio, depending on the conditions of the catalytic reduction of the intermediate 2-nitrophenylpyruvate 2. This reactivity is characteristic in the preparation of 7-substituted indoles.

Reissert indole synthesis - catalytic hydrogenation - substitution effect - indoles - quinolones

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