Synthesis of Some Novel 1,2-Disubstituted Benzimidazole-5-carboxylates via One-Pot Method Using Sodium Dithionite and Its Effect on <i>N</i>-Debenzylation
Vasantha Kumar
Boja Poojary
A. Prathibha
N. Shruthi
10.6084/m9.figshare.1132639.v3
https://tandf.figshare.com/articles/journal_contribution/Synthesis_of_Some_Novel_1_2_Disubstituted_Benzimidazole_5_carboxylates_via_One_Pot_Method_Using_Sodium_Dithionite_and_Its_Effect_on_i_N_i_Debenzylation/1132639
<div><p></p><p>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 <i>N</i>-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 <i>N</i>-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.</p>
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2014-10-15 20:09:40
debenzylation
different
ethanol
sodium
dimethyl
series
purity
method
benzimidazole
ethyl
aid
presence
cyclization
aldehyde
sulfoxide
extent
wide
dithionite
disubstituted
cleavage
workup
cocatalyst
sodium dithionite
alkyl
isolation
variety
nitroreductive
procedure
Synthesi