D. L. Obydennov, G. Röschenthaler, V. Sosnovskikh
Jan 8, 2014
Citations
0
Influential Citations
13
Citations
Journal
Tetrahedron Letters
Abstract
The reaction of 1-aryl-2-(dimethylaminomethylene)butane-1,3-diones with diethyl oxalate in the presence of sodium hydride in THF gave ethyl 5-aroyl-4-oxo-4H-pyran-2-carboxylates, from which 4-oxo-6-aryl-4H-pyran-2-carboxylic acids (6-arylcomanic acids) were obtained in high yields via acid-catalyzed deformylative rearrangement. 5-Aroyl-4-oxo-4H-pyran-2-carboxylic acids (5-aroylcomanic acids) were prepared via а ring-opening/ring-closure sequence by the reaction of 5-aroyl-2-carbethoxy-4-pyrones with piperidine and subsequent basic hydrolysis and acidification.