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Russian Chemical Bulletin

, Volume 66, Issue 11, pp 2136–2141 | Cite as

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

  • V. V. Tkachev
  • Yu. A. Sayapin
  • I. V. Dorogan
  • A. A. Kolodina
  • E. A. Gusakov
  • V. N. Komissarov
  • G. V. Shilov
  • S. M. Aldoshin
  • V. I. Minkin
Full Article
  • 15 Downloads

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)).

Key words

1,2-benzoquinones quinolines 1,3-tropolones intramolecular hydrogen bond X-ray diffraction quantum chemical calculations 

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© Springer Science+Business Media, LLC, part of Springer Nature 2017

Authors and Affiliations

  • V. V. Tkachev
    • 1
  • Yu. A. Sayapin
    • 2
    • 3
  • I. V. Dorogan
    • 2
  • A. A. Kolodina
    • 2
  • E. A. Gusakov
    • 2
  • V. N. Komissarov
    • 2
  • G. V. Shilov
    • 1
  • S. M. Aldoshin
    • 1
  • V. I. Minkin
    • 2
    • 3
  1. 1.Institute of Problems of Chemical PhysicsRussian Academy of SciencesChernogolovkaRussian Federation
  2. 2.Institute of Physical and Organic ChemistrySouthern Federal UniversityRostov-on-DonRussian Federation
  3. 3.Southern Scientific CenterRussian Academy of SciencesRostov-on-DonRussian Federation

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