Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 4, Pages 1162-1167Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo902394y
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Funding
- National Natural Science Foundation of China [20672079]
- Natural Science Foundation of Jiangsu Province [BK2006048]
- Nature Science Key Basic Research of Jiangsu Province for Higher Education [06KJA15007]
- Doctoral Program of Higher Education [20060285001]
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An efficient one-pot synthesis of 4,5,6-triaryl-3,4-dihydropyrimidin-2(1H)-ones via a three-component Biginelli-type condensation of aldehyde, 2-phenylacetophenone, and urea/thiourea in the presence of a catalytic amount of t-BuOK (20 mol %) is described. The reactions proceeded efficiently at 70 degrees C to afford the desired products in moderate to good yields. Detailed mechanistic study shows that the Biginelli-type reaction using urea and thiourea proceeds through two totally different pathways. Enone 5 and bis-urea 8 were highly suggested as respective reaction intermediates for reactions involving thiourea and urea as substrates.
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