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N-Morpholinomethyl-5-lithiotetrazole: A Reagent for the One-Pot Synthesis of 5‑(1-Hydroxyalkyl)tetrazoles

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journal contribution
posted on 16.09.2019, 20:44 by Panagiotis D. Alexakos, Duncan J. Wardrop
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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