Synthesis and structure of 4,6-di(tert-butyl)-2-(4-chloro-7,8-dimethylquinolin-2-yl)-7-(piperidin-1-ylmethyl)-1,3-tropolone

Abstract

The reaction of 4-chloro-2,7,8-trimethylquinoline with 4,6-di(tert-butyl)-3-(piperidin- 1-ylmethyl)-1,2-benzoquinone, which was prepared by the in situ oxidation of 4,6-di(tert- butyl)-3-(piperidin-1-ylmethyl)pyrocatechol with sodium nitrite, gave 4,6-di(tert-butyl)-2- (4-chloro-7,8-dimethylquinolin-2-yl)-7-(piperidin-1-ylmethyl)-1,3-tropolone. Its structure was determined by X-ray diffraction. The energy and structural characteristics of the tauto- mers of this compound in the gas phase and in a polar solution were calculated by quantum chemical methods (PBE0/6-311+G(d,p)).