Selective Protection of Secondary Amines as the <i>N</i>‑Phenyltriazenes. Application to Aminoglycoside
Antibiotics
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Abstract
Selective
protection of secondary amines as triazenes in the presence
of multiple primary amines is demonstrated, with subsequent protection
of the primary amines as either azides or carbamates in the same pot.
Aminoglycoside antibiotic examples reveal broad functional group compatibility.
The triazene group is removed with trifluoroacetic acid and, because
of the low barrier to rotation, affords sharp <sup>1</sup>H NMR spectra
at room temperature