Dual Roles of Methyl Ketones in Radziszewski-Type Reaction: Formal [2 + 1 + 1 + 1] Synthesis of 1,2,5-Trisubstituted Imidazoles

Org Lett. 2016 Apr 1;18(7):1686-9. doi: 10.1021/acs.orglett.6b00607. Epub 2016 Mar 17.

Abstract

A highly efficient molecular iodine mediated Radziszewski-type reaction of methyl ketones, anilines, and tosylmethyl isocyanide has been developed. This protocol represents an elegant molecular fragment assembly of imidazoles via a formal [2 + 1 + 1 + 1] annulation. It is the first example where methyl ketones serve as the α-dicarbonyl compounds and aldehydes in Radziszewski-type reactions.

Publication types

  • Research Support, Non-U.S. Gov't