Structure and Reactivity of Highly Twisted N-Acylimidazoles.

ABSTRACT: A modular and efficient synthesis of highly twisted N-acylimidazoles is reported. These twist amides were characterized via X-ray crystallography, NMR spectroscopy, IR spectroscopy, and DFT calculations. Modification of the substituent proximal to the amide revealed a maximum torsional angle of 88.6° in the solid state, which may be the most twisted amide reported for a nonbicyclic system to date. Reactivity and stability studies indicate that these twisted N-acylimidazoles may be valuable, namely as acyl transfer reagents.

SUBMITTER: Stone EA 

PROVIDER: S-EPMC6461376 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature