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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Employing TosMIC as a C1N1 "Two-Atom Synthon" in Imidazole Synthesis by Neighboring Group Assistance Strategy
Xiao Geng1, Can Wang1, Chun Huang1
1Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry , Central China Normal University , Wuhan 430079 , P. R. China.
Abstract:
We report an I2/FeCl3-co-promoted formal [2 + 2+1] annulation of aryl methyl ketones, 2-aminobenzyl alcohols, and p-toluenesulfonylmethyl isocyanide (TosMIC) by neighboring group (-CH2OH) assistance. This is a novel example of using the Van Leusen reagent as a unique C1N1 "two-atom synthon" in the synthesis of imidazoles. Preliminary mechanism studies showed that TsCH2NH2 might be the key intermediate in this reaction. Furthermore, this reaction not only unlocks a novel strategy for imidazole synthesis, but also exploits a new reactivity of TosMIC.
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