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

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.

• Author: Fredrik Ek; Sophie Manner; Lars-Göran Wistrand; Torbjörn Frejd
• 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
• Links: http://dx.doi.org/10.1021/jo035498c
• 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