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Structure and Reactivity of Highly Twisted N-Acylimidazoles

Author:
Stone, Elizabeth A., Mercado, Brandon Q., Miller, Scott J.
Source:
Organic letters 2019 v.21 no.7 pp. 2346-2351
ISSN:
1523-7052
Subject:
X-ray diffraction, amides, chemical reactions, chemical structure, infrared spectroscopy, nuclear magnetic resonance spectroscopy
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.
Agid:
6363109