Abstract

Triple‐purpose protic ionic liquids were employed as a solvent, a Brønsted acid catalyst, and a source of the nucleophile (thiocyanate‐ion) for the chemodivergent transformation of dihydroimidazolones into 2‐thioxohexahydro‐5H‐imidazo[4,5‐d]oxazol‐5‐ones and tetrahydro‐2H‐imidazo[4,5‐d]thiazole‐2,5(3H)‐diones. An important feature of this process is the switching of its chemoselectivity by simple variation of the reaction temperature, other conditions being the same; this allowed both types of products to be obtained selectively. Straightforward aqueous work‐up of reaction mixture provided crystalline bicyclic products in pure form in an environmentally friendly manner.

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