Synthesis of N-Substituted Aryl Amidines by Strong Base Activation of Amines
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This project describes an efficient method for the direct preparation of N-substituted aryl amidines from nitriles and primary amines. The method employs activation of amines by a strong base and provides greater access to a pharmaceutically relevant functional group. The creation of functionalized amidines and salient amidine-containing moieties via the newly described route was explored. This synthetic approach tolerates deactivated nitriles, nitriles with competing nucleophilic aromatic substitution sites, and aryl amines. Serial amidine formation is also possible, leading to new routes for the creation of tetrahydropyrimidines, benzimidazoles, and bis-amidines. The method described herein features superior yields, improved material and time economy, and greater starting material compatibility compared to other established routes of amidine synthesis. Additionally, this project led to the creation and characterization of six compounds hitherto undescribed in the literature.