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One-pot synthesis of 2-azolylimidazole derivatives through a domino addition/A3 coupling/cyclization process under copper catalysis

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Abstract

A novel one-pot approach for the synthesis of multi-substituted 2-imidazolylimidazoles, 2-pyrazolylimidazoles and 2-indazolylimidazoles was developed through a domino addition/A3 coupling/cyclization process under copper catalysis. A variety of aminoethyl- or hydroxylethyl-tethered 2-azolylimidazole derivatives were conveniently and efficiently assembled in one pot using N-propargylcarbodiimides, azoles, paraformaldehyde and secondary amines as starting materials. The products containing an o-iodoaryl group could be further converted to imidazo[1,2-c]imidazo[1,2-a]quinazoline derivatives through a copper-catalyzed intramolecular C–H arylation.

Graphical abstract: One-pot synthesis of 2-azolylimidazole derivatives through a domino addition/A3 coupling/cyclization process under copper catalysis

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Article information


Submitted
26 Nov 2019
Accepted
29 Jan 2020
First published
29 Jan 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

One-pot synthesis of 2-azolylimidazole derivatives through a domino addition/A3 coupling/cyclization process under copper catalysis

Y. Lin, E. Li, X. Wu, L. Wang, H. Wang, X. Li, H. Kang, L. Zhou, G. Shen and X. Lv, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02532D

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