The synthesis of various heterocycles through dehydrative cyclization is of great importance to medicinal and natural product chemistry. Heterocycles such as oxazolines and thiazolines are prominent in biologically active natural products and compounds with medicinal properties. Previously reported methods used to prepare these heterocycles require stoichiometric use of a dehydrating reagent or suffer from a limited scope. This poster describes a mild catalytic method for dehydrative cyclization reactions using allylic alcohols as electrophilic surrogates and Re2O7 as the catalyst. This method enables the synthesis of 5-membered heterocycles including oxazolines, isoxazolines, and thiazolines, as well as a 6-membered dihydro-1,3-oxazines and dihydro-1,3-thiazines. A wide range of hydroxylamides and α-hydroxyl oximes were converted to the corresponding heterocycles in good to excellent yields.

Re2O7 –Catalyzed dehydrative cyclization reactions in the synthesis of nitrogen containing heterocycles

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.