2-Oxo-2-polyfluoroalkylethane-1-sulfones and -sulfamides in the Biginelli and ‘retro-Biginelli’ reactions |
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Authors: | Vadim M Timoshenko Yuriy M MarkitanovYuriy G Shermolovich |
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Institution: | Institute of Organic Chemistry, NAS of Ukraine, Murmanska St. 5, 02660 Kyiv, Ukraine |
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Abstract: | 2-Oxo-2-polyfluoroalkylethane-1-sulfones and -sulfamides react with aryl aldehydes and urea under Biginelli reaction conditions to yield 4-hydroxy-4-polyfluoroalkyl-5-sulfonyl-6-aryl-tetrahydropyrimidinones. The latter compounds on reaction with hexamethylenetetramine (HMTA) under thermal conditions undergo ‘retro-Biginelli’ reaction involving replacement of the 6-aryl substituent of the pyrimidinone cycle with a hydrogen atom donated by HMTA. Hexamethylenetetramine was employed for the first time in place of formaldehyde in the reported one-step Biginelli protocol for the synthesis of fluorinated sulfonyl-containing 6-unsubstituted tetrahydropyrimidinones. |
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Keywords: | Biginelli reaction Tetrahydropyrimidinone Polyfluoroalkyl Ketosulfone Ketosulfamide Hexamethylenetetramine |
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