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Note | Regular issue | Vol 60, No. 1, 2003, pp.167-175
Published online, 25th November, 2002
DOI: 10.3987/COM-02-9637
An Easy Method for the N-Alkylation of Amides, Carbamates, Ureas and Azoles. Reactivity of 4-Chloromethylpyrazoles with Weak Nucleophiles under Neutral Conditions

Mayoral Elena Pérez and Ballesteros Paloma

*Departamento de Química Orgánica y Biologiá, Faclutade de Ciencias, UNED, Senda del Rey 9, E-28040 Madrid, Spain


4-Chloromethylpyrazoles are shown to react readily with amides, carbamates, ureas and azoles under neutral conditions giving the corresponding N-monoalkylated derivatives with moderate yields. Alkylation of alcohols and thiols occurs under the same conditions. The procedure described may provide a convenient and easy method for the introduction of a 4-pyrazolylmethyl group into molecules containing functional groups with weak nucleophilic character.