Nishant Verma, V. Kundi, Naseem Ahmed
Jul 8, 2015
Citations
0
Influential Citations
9
Citations
Journal
Tetrahedron Letters
Abstract
Piperidine—mediated reactions of 2-acylphenols and 4-nitrobenzaldehydes afforded 3-benzofuranones in high yield (82–95%) at reflux temperature in ethanol. The electron density calculation of HOMO–LUMO energy in the chalcone intermediates by DFT showed the influence of the 4-nitro group and alkyl chain at C-2 position for the regioselective products. However, the reaction of 2- and 3-nitrobenzaldehydes with 2-acylphenols afforded flavones and flavanones, respectively, under the same reaction conditions. The substituent position effects were further studied in respect of 2-, 3- and 4-nitro substituted benzaldehydes and 2-acylphenols in the product formation.