Synthesis and structure of 5,7-diisopropyl-2-(quinolin-2-yl)-1,3-tropolone derivatives

Abstract

A synthetic procedure towards 4,6-diisopropyl-3-nitro-1,2-benzoquinone was elaborated. Based on this benzoquinone, a series of novel 5,7-diisopropyl-2-(quinolin-2-yl)-1,3-tropolones and 5,7diisopropyl-2-(quinolin-2-yl)-4-nitro-1,3-tropolones were derived. Molecular structure of 2-(4-chloro-8-methylquinolin-2-yl)-5,7-diisopropyl-1,3-tropolone was established by X-ray diffraction analysis. Energetic and structural characteristics of isomeric 5,7-diisopropyl-2-(quinolin-2yl)-1,3-tropolones and 5,7-diisopropyl-2-(quinolin-2-yl)-4-nitro-1,3-tropolones in the gas phase and in the polar solvent were calculated by quantum chemistry method (PBE0/6-311+G(d,p)).