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

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Abstract

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.

Detaljer

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Forskningsområden

Ämnesklassifikation (UKÄ) – OBLIGATORISK

  • Organisk kemi
Originalspråkengelska
Sidor (från-till)1346-1352
TidskriftJournal of Organic Chemistry
Volym69
Utgivningsnummer4
StatusPublished - 2004
PublikationskategoriForskning
Peer review utfördJa