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Sophie Manner

Director of studies

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Synthesis of fused tetrazole derivatives via a tandem cycloaddition and N-allylation reaction and parallel synthesis of fused tetrazole amines

Author

  • Fredrik Ek
  • Sophie Manner
  • Lars-Göran Wistrand
  • Torbjörn Frejd

Summary, in English

A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddition between a nitrile and (TMS)N-3 followed by an intramolecular N-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An exo-methylene group in these new compounds permitted further derivatization. Structural resemblance with substances which possess important pharmacological properties motivated the synthesis of a series of ketones and a small library of amines.

Department/s

  • Chemical Biology and Therapeutics
  • Centre for Analysis and Synthesis

Publishing year

2004

Language

English

Pages

1346-1352

Publication/Series

Journal of Organic Chemistry

Volume

69

Issue

4

Document type

Journal article

Publisher

The American Chemical Society (ACS)

Topic

  • Organic Chemistry

Status

Published

Research group

  • Chemical Biology and Therapeutics

ISBN/ISSN/Other

  • ISSN: 1520-6904