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Paper | Special issue | Vol 73, No. 1, 2007, pp.469-480
Published online, 27th July, 2007
DOI: 10.3987/COM-07-S(U)19
Multicomponent Cyclocondensations of β-Ketosulfones with Aldehydes and Aminoazole Building Blocks

Eugene S. Gladkov,* Valentin A. Chebanov, Sergey M. Desenko, Oleg V. Shishkin, Svetlana V. Shishkina, Doris Dallinger, and C. Oliver Kappe*

*Christian Doppler Laboratory for Microwave Chemistry (CDLMC) and Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz, Austria


The multicomponent reaction of methylsulfonylacetone (or α-methylsulfonylacetophenone) with aromatic aldehydes and aminoazoles (or urea) under microwave irradiation to yield 5,8-dihydroimidazolo[1,2-a]pyrimidines and 4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidines was studied. The influence of the type of aminoazole building block on the reactivity was established. In addition, an unusual reaction pathway for the Biginelli-type condensation of methylsulfonylacetone with aldehydes and urea leading to non-classical Hantzsch-type dihydropyridines was found.