Abstract
A series of polyfunctional N H-1,2,3-triazoles were prepared directly from propargyl halides and nucleophiles using a powerful, albeit little appreciated, synthetic sequence we call the Banert cascade. Propargyl azides, prepared in situ from propargyl halides or sulfonates, underwent a thermal rearrangement sequence to triazafulvene intermediates, potent electrophiles, which were readily captured by diverse nucleophiles. Using this cascade, a series of racemic azidomethyl(hydroxymethyl)-N H-1,2,3-triazoles were prepared by a two-step protocol that commences with the addition of propargyl chloride to aldehydes and ketones.
Key words
triazoles - heterocycles - azides - rearrangements - alkynes - cyclizations - Banert cascade
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