Synthesis and structure of regioisomeric amino enones containing 2-pyridyl and CF3 substituents
Autor: | V. N. Charushin, Pavel A. Slepukhin, N. S. Boltacheva, Marina G. Pervova, Vera I. Filyakova |
---|---|
Rok vydání: | 2020 |
Předmět: | |
Zdroj: | Russian Chemical Bulletin. 69:2355-2362 |
ISSN: | 1573-9171 1066-5285 |
DOI: | 10.1007/s11172-020-3030-1 |
Popis: | Regioisomeric amino enones (Z)-4-amino-1,1,1-trifluoro-4-(2-pyridyl)but-3-en-2-one and (Z)-3-amino-4,4,4-trifluoro-1-(2-pyridyl)but-2-en-1-one were synthesized by the reaction of lithium (Z)-1,1,1-trifluoro-4-oxo-4-(2-pyridyl)but-2-en-2-olate with ammonium acetate in glacial AcOH. A comparative study of physicochemical properties and the crystal structures showed that the molecules of these new compounds are planar (except for two fluorine atoms) with an U-shaped configuration of the keto enamine moiety. A change in the position of the amino group with respect to the CF3 substituent leads to significant changes in the electron density distribution and the C-C bond lengths in the keto enamine moiety and also in the character of intermolecular hydrogen bonds responsible for the crystal packing mode of regioisomeric amino enones. |
Databáze: | OpenAIRE |
Externí odkaz: |