Heterocyclic compounds are of crucial importance to medicinal chemists as the majority of active pharmaceutical ingredients contain at least one heterocycle in their scaffold. Likewise, many agrochemicals contain heterocycles. While nitrogen and oxygen heterocycles make up the majority of these compounds, sulfur containing heterocycles are becoming increasingly important.<br/><br/>The Bolliger group has developed a new strategy to prepare both charged and neutral tricyclic sulfur and nitrogen containing heterocycles. The target compounds are conveniently obtained from air stable precursor via selective deprotection of a thiol followed by on oxidative cyclization. Using this procedure, it is possible to obtain a variety of thiazolium salts (Figure 1a) which contain both electron-withdrawing and electron donating aromatic substituents as well as aliphatic substituents. Our research group was able to expand this C-H activation and oxidative cyclization to uncharged heterocycles (Figure 1b). In both cases, this method has proven to be tolerant towards many functional groups, thus allowing biologically relevant groups to be introduced either before or after the heterocycle formation.<br/>Additional experiments to elucidate the mechanism of this oxidative cyclization will be presented during the meeting.

New oxidative strategies for the synthesis of sulfur containing heterocycles

ACS Fall 2021

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