Download PDF
Synthesis 1992; 1992(5): 473-476
DOI: 10.1055/s-1992-26140
paper
© 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.

Reaction of 3H-Pyrano[3,4-b]indol-3-ones and 3H-2-Benzopyran-3-ones with Heterodienophiles: A Two Step Synthesis for Some 9H-Pyrido[3,4-b]indoles and Isoquinolines

P. Van Broeck* , P. Van Doren, G. Hoornaert
  • *Laboratorium voor Organische Synthese, K. U. Leuven, Celestijnenlaan 200 F, B-3001 Heverlee Belgium
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

A short synthetic method for 3-substituted 9H-pyrido[3,4-b] indoles 3 and isoquinolines 7 is proposed using cycloaddition-elimination reactions between 3H-pyrano[3,4-b]indol-3-ones 1 or 3H-2-benzopyran-3-ones 6 and electron-poor nitriles as ethyl cyanoformate and p-toluenesulfonyl cyanide. Extension of the method is possible neither with benzoyl cyanide nor with imines. The diene system undergoes cycloaddition with the carbonyl function of the former compound; subsequent elimination of carbon dioxide followed by an electrocyclic reaction involving the C-O bond gives ring opened ketonic compounds. Imines attack the lactone function of the pyranone system yielding ultimately a ß-lactam in some cases.

      >