Synthesis of CF3‑Containing 2‑Imidazolines and Imidazoles via a Iodide-Promoted [3 + 2] Cyclization Reaction
The Journal of organic chemistry(2023)
摘要
We report herein a general and effective system achieving cyclization of beta-trifluoromethyl enones with amidines in the presence of 1,3-diiodo-5,5-dimethylhydantoin (DIH), which affords a range of trifluoromethylated 2-imidazolines in synthetically useful yields with good diastereoselectivities (up to 95% yield, up to 98:2 dr) and good functional group tolerance. Furthermore, the one-pot synthesis of trifluoromethylated imidazoles via sequential cyclization and oxidation is demonstrated. More significantly, the reaction mechanism was verified by ESI-MS studies of possible intermediates, and a reasonable reaction mechanism was proposed.
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关键词
imidazoles,synthesis,iodide-promoted
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