Synthesis and Molecular Structures of (3-Hydroxy, 3-Chloro, 3-Arylamino)-N-acetyl-3-arylaminotropones

Abstract

The structures of 5,7-di(tert-butyl)-2-(5,8-dimethyl-4-piperidinoquinolin-2-yl)-3-hydroxytropone, 5,7-di(tert-butyl)-3-chloro-2-(5,8-dimethyl-4-piperidinoquinolin-2-yl)tropone, 5,7-di(tert-butyl)- 3-(3,5-dimethylphenylamino)-2-(5,8-dimethyl-4-piperidinoquinolin-2-yl)tropone, and 3-(N-acetyl-3,5- dimethylphenylamino)-5,7-di(tert-butyl)-2-(5,8-dimethyl-4-piperidinoquinolin-2-yl)tropone were determined by X-ray diffraction. These compounds were synthesized through a series of transformations, including the nucleophilic substitution of the chlorine atom by piperidine in the starting 5,7-di(tert-butyl)-2-(4- chloroquinolin-2-yl)-3-hydroxytropone followed by the three-step functionalization of the 3-position in 3-hydroxytropone. The nature of dynamic processes in a solution of N-acetyl-3-arylaminotropone associated with the rotation of the N-acetyl group was revealed by the PCM/PBE0/6-31G(d,p) method.