Interaction of polyfluorinated 2-chloroquinolines with ammonia
| Autor: | Vitalij D. Shteingarts, Galina A. Selivanova, Evgeny V. Tretyakov, Larisa Yu. Gurskaya, Tatjana F. Bogdanova, Lyudmila N. Shchegoleva, Irina Yu. Bagryanskaya, Alexandrina D. Skolyapova |
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| Rok vydání: | 2017 |
| Předmět: |
Aqueous solution
010405 organic chemistry Organic Chemistry Regioselectivity Activation energy 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Ammonia chemistry.chemical_compound chemistry Yield (chemistry) Drug Discovery Organic chemistry Moiety Aminoquinolines Benzene |
| Zdroj: | Tetrahedron. 73:1219-1229 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2017.01.026 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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