Heterocyclic compounds are widely distributed in nature and have much biological and medicinal importance. Most of the drugs available in the market are heterocyclic structures. Among the heterocyclic structures, molecules containing pyridine motif are very important. The pyridine ring systems have emerged as integral backbones of over 7000 existing drugs [1]. Cyanopyridines are one of the most important derivatives of pyridine, which they have represent a wide variety of biological applications [2]. Ionic liquids (ILs) are persuasive areas of chemistry in the past decade. They have many advantages including negligible vapor pressure, designable properties, simplified separation of products and potential reuse [3] In this study, we synthesized and applied an imidazolium-based IL for the preparation of new indole linked pyridine systems via a cooperative vinylogous anomeric based oxidation (Figure 1).