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Efficient and “Green” Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)–Ascorbate-Catalyzed A3-Coupling in Aqueous Micellar Media

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An efficient and environmentally sustainable method for the synthesis of imidazo[1,2-a]pyridine derivatives by domino A3-coupling reaction catalyzed by Cu(II)–ascorbate was developed in aqueous micellar media in the presence of sodium… Click to show full abstract

An efficient and environmentally sustainable method for the synthesis of imidazo[1,2-a]pyridine derivatives by domino A3-coupling reaction catalyzed by Cu(II)–ascorbate was developed in aqueous micellar media in the presence of sodium dodecyl sulfate (SDS). The catalyst, a dynamic combination of Cu(II)/Cu(I), was generated in situ in the reaction mixture by mixing CuSO4 with sodium ascorbate and aided a facile 5-exo-dig cycloisomerization of alkynes with the condensation products of 2-aminopyridines and aldehydes to afford a variety of imidazo[1,2-a]pyridines in good overall yields. A simple experimental setup, water as the “green” medium, and inexpensive catalyst and auxiliary are some of the merits of this protocol.

Keywords: ascorbate; imidazo pyridine; aqueous micellar; imidazo; micellar media

Journal Title: ACS Omega
Year Published: 2019

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