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A sequential one-pot approach to 1,2,4,5-tetrasubstituted-2H-imidazole synthesis from disubstituted alkynes†
Siva Senthil Kumar Boominathan,Chung-Yu Chen,Po-Jui Huang,Ruei-Jhih Hou,Jeh-Jeng Wang
New Journal of Chemistry Pub Date : 06/29/2015 00:00:00 , DOI:10.1039/C5NJ00959F
Abstract

A sequential one-pot approach to the tetrasubstituted 2H-imidazole scaffolds has been developed from disubstituted alkynes and structurally diverse ketones. The reaction proceeds via a diketo intermediate generated from internal alkynes followed by the addition of ammonium acetate and a suitable ketone, affording a diverse range of 2H-imidazoles. Using air-moisture stable reaction conditions and inexpensive reagents, the transformation demonstrates a broad substrate scope and good functional group compatibility.

Graphical abstract: A sequential one-pot approach to 1,2,4,5-tetrasubstituted-2H-imidazole synthesis from disubstituted alkynes
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