An efficient, one-pot
method for the preparation of 5-(1-hydroxyalkyl)tetrazoles
is reported. N-Morpholinomethyl-5-lithiotetrazole,
generated by the deprotonation of 4-(N-tetrazolylmethyl)morpholine
with LiHMDS, undergoes addition to ketones and aldehydes (both aromatic
and aliphatic) to form 5-(1-hydroxyalkyl)tetrazoles in a high yield,
after acidic workup. The reported protocol displays a broad substrate
scope and functional group tolerance, avoids the use of cyanide- or
azide-based reagents, and provides access to sterically congested
and unsaturated tetrazoles, which are difficult to access by other
means.
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