Synthesis and Molecular Structures of (3-Hydroxy, 3-Chloro, 3-Arylamino)-<Emphasis Type="Italic">N</Emphasis>-acetyl-3-arylaminotropones |
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| Authors: | V V Tkachev Yu A Sayapin E A Gusakov A A Kolodina I V Dorogan G V Shilov S M Aldoshin V I Minkin |
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| Institution: | 1.Institute of Problems of Chemical Physics,Russian Academy of Sciences,Chernogolovka, Moscow Region,Russia;2.Southern Scientific Center,Russian Academy of Sciences,Rostov-on-Don,Russia;3.Institute of Physical and Organic Chemistry,Southern Federal University,Rostov-on-Don,Russia |
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| 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. |
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