jo035498c_si_002.pdf (4.77 MB)
Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and N-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines
journal contribution
posted on 2004-02-20, 00:00 authored by Fredrik Ek, Sophie Manner, Lars-Göran Wistrand, Torbjörn FrejdA 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)N3 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.
History
Usage metrics
Categories
Keywords
allylic bromidesseriesallylationParallel SynthesisderivatizationTMSpuritycycloadditionFused Tetrazole Derivativestricyclic tetrazolessynthesisStructural resemblanceaminescompoundmethylene groupAllylation ReactionvariationfunctionalitieTandem CycloadditionnitrileDiazAll reactionFused Tetrazole Aminesbenzene moietyexomethodtandem reactionketoneintramolecular N
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC