Synthesis, structure and reactivity of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole

Sparke, Amanda E.; Fisher, Christopher M.; Mewis, Ryan E.; Archibald, Stephen J.

Abstract

The synthesis of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole, which undergoes a nucleophilic substitution with pyridine in the absence of additional base, is reported. The key steps are the reaction of 1,2-phenylenediamine to give exclusively the mono-substituted product and the avoidance of minor by-products via the use of glycolic acid for the cyclisation step. The X-ray structures of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazolium chloride and 1-[1-(4-nitrobenzyl)benzimidazol-2-ylmethyl]pyridinium chloride are presented. © 2010 Elsevier Ltd. All rights reserved.

Citation

Sparke, A. E., Fisher, C. M., Mewis, R. E., & Archibald, S. J. (2010). Synthesis, structure and reactivity of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 51(36), 4723-4726. https://doi.org/10.1016/j.tetlet.2010.07.010

• Journal Article Type: Article
• Acceptance Date: Jul 2, 2010
• Online Publication Date: Jul 7, 2010
• Publication Date: Sep 8, 2010
• Journal: TETRAHEDRON LETTERS
• Print ISSN: 0040-4039
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 51
• Issue: 36
• Pages: 4723-4726
• DOI: https://doi.org/10.1016/j.tetlet.2010.07.010
• Keywords: Benzimidazole; Antagonist; Anti-viral; Chelators synthesis
• Public URL: https://hull-repository.worktribe.com/output/400147