Novel and convenient synthesis of 1-(pyridinylmethyl)-2-naphthols and 1-(pyridinylmethylene)-2-tetralones from 2-tetralones |
| |
Authors: | Po-Jung J. Huang Elizabeth Potter Amitabh Jha |
| |
Affiliation: | 1.Department of Chemistry,Acadia University,Wolfville,Canada |
| |
Abstract: | The reaction of 2/4-pyridine carboxaldehyes with 2-tetralone analogs in the presence of catalytic amounts of Pd/C and trimethylsilyl chloride in DMF resulted in the formation of 1-(pyridin-2/4-ylmethyl)-2-naphthols in moderate to good yields as opposed to the expected 1-(pyridin-2/4-ylmethylene)-2-tetralones. 3-Pyridine carboxaldehyde, however, formed 1-(pyridin-3-ylmethylene)-2-tetralones with 2-tetralone analogs under similar conditions. When representative reactions were repeated in the presence of anhydrous HCl gas in acetic acid, including one with 3-pyridine carboxaldehyde, 1-(pyridinylmethyl)-2-naphthols were the only products obtained with significantly improved yields. A possible mechanism explaining these results is discussed. |
| |
Keywords: | |
本文献已被 SpringerLink 等数据库收录! |
|