Unexpected Reduction of C-Cl Bond to C-H Bond by Hydrazine-Mediated Reaction During the Synthesis of Alkylbenzimidazoles Derivatives
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Keywords

Reduction; Hydrazine; Diimide; o-Phenylenediamines; 2-alkylbenzimidazoles

How to Cite

Mahdavi , B. (2013). Unexpected Reduction of C-Cl Bond to C-H Bond by Hydrazine-Mediated Reaction During the Synthesis of Alkylbenzimidazoles Derivatives. Jordan Journal of Chemistry (JJC), 8(1), 63-69. Retrieved from http://jjc.yu.edu.jo/index.php/jjc/article/view/193

Abstract

Acid-catalyzed cyclocondensation of 2-chloroacetic acid and 2-chloropropionic acid with some substituted o-phenylenediamines afforded the corresponding 2-(1-chloroalkyl)benzimidazoles. Upon treatment with hydrazine hydrate, in order to obtain hydrazine-containing compounds as suitable precursors for construction of new heterocyclic systems, the latter compounds underwent an overall unexpected reduction of the C‑Cl bond to C-H bond in a sequence of SN2 followed by bonds (atom) rearrangment to furnish 2-alkylbenzimidazoles.

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