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Springer, Russian Chemical Bulletin, 2(62), p. 480-491, 2013

DOI: 10.1007/s11172-013-0067-4

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Synthesis and structure of 3-arylamino-2-(quinolin-2-yl)tropones

Journal article published in 2013 by Y.-U. A. Sayapin ORCID, E. A. Gusakov, Zyong Ngia Bang, I. O. Tupaeva, V. N. Komissarov, I. V. Dorogan, V. V. Tkachev, S. M. Aldoshin, V. I. Minkin
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

A reaction of substituted 2-(quinolin-2-yl)-1,3-tropolones with POCl3 leads to the new3-chloro-2-(quinolin-2-yl)tropone derivatives. New 2-(4-arylaminoquinolin-2-yl)-3-aryl-aminocyclohepta-2,4,6-trien-1-ones and 2-[4-morpholino(piperidino)quinolin-2-yl]-3-aryl-aminocyclohepta-2,4,6-trien-1-ones were obtained by nucleophilic substitution reaction of the halogen atom in 2-(4-chloroquinolin-2-yl)-3-chlorotropones and 3-chloro-2-[4-morpholino-(piperidino)quinolin-2-yl]tropones. Molecular structures of 3-chloro-2-(quinolin-2-yl)tropone and 3-arylamino-2-(quinolin-2-yl)tropone were established by X-ray diffraction analysis. Energy and structural characteristics of isomers of 3-arylamino-2-(quinolin-2-yl)tropones in the gas phase and in solution were calculated by the density functional theory method (PBE0/6-31G**).