Abstract
A number of N-aminomerhyl and N-alkoxy(aroxy)methylbenzimidazoles are prepared. These compounds are decomposed in acid solution, giving benzimidazole. Sodamide reacts with them to give N-aminomethylbenzimidazole, and not the corresponding 2-amino derivative. The facility with which the compounds investigated decompose decreases in the order N-aminomethyl > N-aroxymethyl > N-alkoxymethylbenzimidazole. The mechanism of splitting is considered.
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Pozharskii, A.F., Simonov, A.M., Zvezdina, E.A. et al. Imidazole derivatives with potentially labile groups at the N-atom. Chem Heterocycl Compd 3, 703–705 (1967). https://doi.org/10.1007/BF00468352
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DOI: https://doi.org/10.1007/BF00468352