Synthesis of Some Novel 1,2-Disubstituted Benzimidazole-5-carboxylates via One-Pot Method Using Sodium Dithionite and Its Effect on N-Debenzylation

Abstract

A series a novel of 1,2-disubstituted benzimidazole-5-carboxylates were prepared by the one-pot nitroreductive cyclization route using sodium dithionite, and its effect on N-debenzylation has been described. Different ethyl 4-(alkyl/arylamino)-3-nitrobenzoates were reacted with various aromatic/heteroaromatic aldehydes in dimethyl sulfoxide to yield the target benzimidazoles in good yield and purity. Wide varieties of aldehydes used for the cyclization were found to be susceptible under the reaction conditions. This method afforded the products within a very short reaction time and isolation was an easy workup procedure. Debenzylation resulting in the cleavage of the N-benzyl group was observed under experimental conditions with sodium dithionite without the aid of any cocatalyst and the presence of ethanol increased the extent of debenzylation.

GRAPHICAL ABSTRACT

Keywords:

• N-Debenzylation
• 1,2-disubstituted benzimidazoles
• one-pot method
• reductive cyclization
• sodium dithionite

Notes

^a Isolated yield.

^b Incomplete reaction.

^a Isolated yield.

^a Isolated yield.

^b Incomplete reaction detected by TLC.