Synthesis, molecular and crystal structures of new amino enones containing trifluoromethyl and 3-or 4-pyridyl substituents

被引：0

作者：

Boltacheva, N. S. ^{[1
]}

Slepukhin, P. A. ^{[1
,2
]}

Pervova, M. G. ^{[1
]}

Chizhov, D. L. ^{[1
]}

Filyakova, V. I. ^{[1
]}

Charushin, V. N. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, I Ya Postovsky Inst Organ Synth, Ural Branch, 22-20 Ul S Kovalevskoy, Ekaterinburg 620066, Russia

[2] Ural Fed Univ, 19 Ul Mira, Ekaterinburg 620002, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2025年 / 74卷 / 02期

关键词：

amino enones; azaheterocyclic compounds; organofluorine compounds; synthesis; molecular structure; crystal structure; COMPLEXES; COPPER(II); NICKEL(II); FLUOROALKYL; METALLOMESOGENS; PALLADIUM(II); LIGANDS; NI(II); CU(II);

D O I：

10.1007/s11172-025-4537-2

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of lithium (Z)-1,1,1-trifluoro-4-oxo-4-(pyridin-3-yl)- or (Z)-1,1,1-trifluoro-4-oxo-4-(4-pyridin-4-yl)but-2-en-2-olate with ammonium acetate in glacial AcOH afforded new amino enones containing an amino group geminal to the fluoroalkyl substituent, (Z)-3-amino-4,4,4-trifluoro-1-(pyridin-3-yl)- and (Z)-3-amino-4,4,4-trifluoro-1-(pyridin-4-yl)but-2-en-1-one, respectively. On heating in AcOH under reflux, (Z)-3-amino-4,4,4-trifluoro-1-(pyridin-3-yl)but-2-en-1-one undergoes a series of transformations, giving 7-trifluoromethyl-1,6-naphthyridine as one of the products. A comparative study of the physicochemical parameters and the crystal structures of amino enones containing a CF3 group and 2-, 3-, or 4-pyridyl substituents was performed.

引用

收藏

页码：451 / 460

页数：10

相关论文

共 37 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2] A cartography of the van der Waals territories [J].

Alvarez, Santiago .

DALTON TRANSACTIONS, 2013, 42 (24) :8617-8636

[3] A nonanuclear dysprosium (III)-copper(II) complex exhibiting single-molecule magnet behavior with very slow zero-field relaxation [J].

Aronica, Christophe ;

Pilet, Guillaume ;

Chastanet, Guillaume ;

Wernsdorfer, Wolfgang ;

Jacquot, Jean-Francois ;

Luneau, Dominique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (28) :4659-4662

[4] Fluoroalkyl-containing lithium 1,3-diketonates in reactions with amines and ammonium salts [J].

Boltacheva, NS ;

Filyakova, VI ;

Charushin, VN .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 41 (10) :1452-1457

[5] Fluorinated lithium 1,3-diketonates as reagents to modify podands and crown-ethers [J].

Boltachova, Nadezhda S. ;

Fedorova, Olga V. ;

Ovchinnikova, Irina G. ;

Kazheva, Olga N. ;

Chekhlov, Anatoliy N. ;

Dyachenko, Oleg A. ;

Rusinov, Gennady L. ;

Filyakova, Vera I. ;

Charushin, Valeriy N. .

JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (07) :762-768

[6] Trialkyl borate assisted amination of fluorinated 1,3-diketones for synthesis of N,N′-1,2-phenylen-bis(β-aminoenones) and their Ni(II), Cu(II) and Pd(II) complexes [J].

Chizhov, Dmitrii L. ;

Pervova, Marina G. ;

Samorukova, Mariya A. ;

Khmara, Ekaterina F. ;

Filyakova, Vera I. ;

Saloutin, Viktor I. ;

Charushin, Valery N. .

JOURNAL OF FLUORINE CHEMISTRY, 2011, 132 (06) :394-401

[7] A versatile ethanolamine-derived trifluoromethyl enaminone ligand for the elaboration of nickel(II) and copper(II)-dysprosium(III) multinuclear complexes with magnetic properties [J].

Chopin, Nicolas ;

Novitchi, Ghenadie ;

Medebielle, Maurice ;

Pilet, Guillaume .

JOURNAL OF FLUORINE CHEMISTRY, 2015, 179 :169-174

[8] Quenching of Fluorescence in Bodipy-Derived Trifluoromethyl Enaminone Ligands upon Coordination to Copper(II) [J].

Chopin, Nicolas ;

Medebielle, Maurice ;

Maury, Olivier ;

Novitchi, Ghenadie ;

Pilet, Guillaume .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2014, (36) :6185-6195

[9] 8-Aminoquinoline and 2-aminopyridine trifluoromethyl-derived enaminone ligands and their Co(II), Ni(II) and Zn(II) metal complexes: Structural arrangements due to F•••H interactions [J].

Chopin, Nicolas ;

Medebielle, Maurice ;

Pilet, Guillaume .

JOURNAL OF FLUORINE CHEMISTRY, 2013, 155 :89-96

[10] Copper(II) Cubane Complexes Built from Electro- and Photosensitive β-Aminovinyl Trifluoromethyl Ketone Ligands [J].

Chopin, Nicolas ;

Chastanet, Guillaume ;

Le Guennic, Boris ;

Medebielle, Maurice ;

Pilet, Guillaume .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (31) :5058-5070

← 1 2 3 4 →