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

TY - JOUR

T1 - Synthesis, structure and reactivity of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole

AU - Sparke, Amanda E.

AU - Fisher, Christopher M.

AU - Mewis, Ryan E.

AU - Archibald, Stephen J.

PY - 2010/9/8

Y1 - 2010/9/8

N2 - 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.

AB - 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.

KW - Antagonist

KW - Anti-viral

KW - Benzimidazole

KW - Chelators synthesis

UR - http://www.scopus.com/inward/record.url?scp=77955468071&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.07.010

DO - 10.1016/j.tetlet.2010.07.010

M3 - Article

AN - SCOPUS:77955468071

SN - 0040-4039

VL - 51

SP - 4723

EP - 4726

JO - TETRAHEDRON LETTERS

JF - TETRAHEDRON LETTERS

IS - 36

ER -