4.8 Article

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

Journal

ORGANIC LETTERS
Volume 18, Issue 7, Pages 1686-1689

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00607

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Funding

  1. National Natural Science Foundation of China [21272085, 21472056]
  2. excellent doctorial dissertation cultivation grant from Central China Normal University [2015YBYB019]

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A highly efficient molecular iodine mediated Radziszewski-type reaction of methyl ketones, anilines, and tosylinethyl 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 alpha-dicarbonyl compounds and aldehydes in Radziszewski-type reactions.

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