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1. Lithium Hexamethyldisilazane Transformation of Transiently Protected 4-Aza/Benzimidazole Nitriles to Amidines and their Dimethyl Sulfoxide Mediated Imidazole Ring Formation.

Author

Abou-Elkhair RA, Hassan AE, Boykin DW, and Wilson WD

Subjects
Amidines chemistry, Aza Compounds chemical synthesis, Benzimidazoles chemical synthesis, Dimethyl Sulfoxide chemistry, Imidazoles chemistry, Molecular Structure, Nitriles chemical synthesis, Amidines chemical synthesis, Aza Compounds chemistry, Benzimidazoles chemistry, Imidazoles chemical synthesis, Lithium Compounds chemistry, Nitriles chemistry, Silanes chemistry
Abstract

Trimethylsilyl-transient protection successfully allowed the use of lithium hexamethyldisilazane to prepare benzimidazole (BI) and 4-azabenzimidazole (azaBI) amidines from nitriles in 58-88% yields. This strategy offers a much better choice to prepare BI/azaBI amidines than the lengthy, low-yielding Pinner reaction. Synthesis of aza/benzimidazole rings from aromatic diamines and aldehydes was affected in dimethyl sulfoxide in 10-15 min, while known procedures require long time and purification. These methods are important for the BI/azaBI-based drug industry and for developing specific DNA binders for expanded therapeutic applications.

Published
2016
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