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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.

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.

SUBMITTER: Bhutia ZT

PROVIDER: S-EPMC6647986 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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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.

Bhutia Zigmee T ZT Das Dharmendra D Chatterjee Amrita A Banerjee Mainak M

ACS omega 20190301 3

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 c ...[more]

PMID: 31459643

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