13527-91-8Relevant articles and documents
Synthesis and thiolation of 1,3-difluoro-2,4,6-trihaloanilines and benzenes
Manka, Jason T.,Kaszynski, Piotr
, p. 39 - 43 (2003)
Three pentahaloanilines were prepared by stepwise halogenation of 3,5-difluoroaniline and were deaminated to form pentahalobenzenes. Alternatively, two pentahalobenzenes were obtained by lithiation followed by iodination of 1,3-difluoro-4,6-dihalobenzenes
Interaction of polyfluorinated 2-chloroquinolines with ammonia
Skolyapova, Alexandrina D.,Selivanova, Galina A.,Tretyakov, Evgeny V.,Bogdanova, Tatjana F.,Shchegoleva, Lyudmila N.,Bagryanskaya, Irina Yu.,Gurskaya, Larisa Yu.,Shteingarts, Vitalij D.
supporting information, p. 1219 - 1229 (2017/02/18)
We have studied the interaction of polyfluorinated (in the benzene moiety) 2-chloroquinolines with liquid and aqueous ammonia as an approach to the synthesis of halogen-containing aminoquinolines. 5,7-Difluoro-, 5,6,8-trifluoro-, and 5,7,8-trifluoro-2-chloroquinolines mostly form products of substitution of the Cl atom, whereas 5,7-difluoro-2,6-dichloroquinoline, 5,6,7,8-tetrafluoro-, and 6,7-difluoro-2-chloroquinolines yield products of substitution of an F atom at various positions. The replacement of liquid ammonia with aqueous causes an increase in the proportion of the products of aminodechlorination relative to the products of aminodefluorination. For 2-chloro-6,8-difluoroquinoline this replacement leads to 2-amino-6,8-difluoroquinoline as the main product instead of the 8-amino-derivative. Activation energy values estimated by DFT calculations for the reactions in question agree with the reaction regioselectivity observed experimentally.