Download PDF
Synlett 2000; 2000(8): 1196-1198
DOI: 10.1055/s-2000-6758
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >