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:	010405 organic chemistry Chemistry Hydrogen bond Substituent General Chemistry Crystal structure 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Enamine Bond length chemistry.chemical_compound Molecule Moiety Ammonium acetate
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
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