(Z)-N'-(1H-Benzo[d]imidazol-2-Yl)-Arylimidamide Adducts of 2-Aminobenzimidazole and Aromatic Nitriles: Structural and Spectroscopic Proof of Regiochemical and Stereochemical Outcomes

28 February 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The selection of a core scaffold or template is of enormous importance in medicinal chemistry. Benzimidazoles are a recurring fragment in medicinal chemistry, and the 2-amino derivative is a versatile example in lead generation. Alkylated and acylated examples abound, however, alternative linkage chemistries leading do more diverse structures are needed.
Here we discuss the regiochemistry of nucleophilic addition of 2-aminobenzimidazole to nitriles, leading to imidamide (amidine) adducts. Additionally, we use extensive NMR analysis and ultimately X-ray crystallography to demonstrate both the regiochemistry and stereochemistry of the addition products, arising from derivatisation of the exocylic 2-amino group.

Keywords

aminobenzimidazole
nucleophilic addition
X-ray crystallography
regiochemistry
imidamide

Supplementary materials

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k66-99expanded
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k66-99
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K66 99 sub
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Stoermer Amidines SI ChemRxiv sub
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