Literature DB >> 30860852

Structure and Reactivity of Highly Twisted N-Acylimidazoles.

Elizabeth A Stone1, Brandon Q Mercado1, Scott J Miller1.   

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.

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Year:  2019        PMID： 30860852      PMCID： PMC6461376          DOI： 10.1021/acs.orglett.9b00624

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  41 in total

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