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Org Lett. 2019 Apr 5;21(7):2346-2351. doi: 10.1021/acs.orglett.9b00624. Epub 2019 Mar 12.

Structure and Reactivity of Highly Twisted N-Acylimidazoles.

Author information

1
Department of Chemistry , Yale University , 225 Prospect Street , New Haven , Connecticut 06520-8107 , United States.

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.

PMID:
30860852
PMCID:
PMC6461376
[Available on 2020-04-05]
DOI:
10.1021/acs.orglett.9b00624

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