The synthesis of medium-ring heterocycles remains a challenge largely due to unfavorable energetic factors. In fact, a recent feature article in Chemical Communications (Sharma, A.; Appukkuttan, P.; Van der Eycken, E., Microwave-assisted synthesis of medium-sized heterocycles. Chem. Commun. 2012  , 48, 1623-1637) was dedicated specifically to this topic. We are reporting a synthetic methodology that leads to the quantitative formation of a variety of heterocycles. The reactions are typically complete in 5 min, require no solvent, and the only byproducts are acetone and water. The reaction products can be isolated in pure form by simply placing the mixture under vacuum. The reactions led to higher yields than those detailed in the feature article mentioned above, and demonstrated a wider applicability in terms of ring sizes accessible by a single reaction methodology. This reaction sequence possesses many of the hallmarks of a click reaction. A variety of privileged structures should be accessible via this methodology by simply changing the bi-nucleophilic species. Details of the scope of the reaction will be discussed.

Synthesis of medium ring heterocycles via reaction of diketene acetone adduct with binucleophilic species under green reaction conditions

247th National Meeting (2014)

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