Synthesis and study of structural, conformational and vibrational properties of a new trifluoroacetylureide from trifluoromethyl chromone

L.P. AVENDAÑO JIMÉNEZ; G. A. ECHEVERRÍA; O. E. PIRO; J.L. JIOS; S.E. ULIC

Carlos Paz

Conferencia; 13a Conferencia Latinoamericana de Físico-Química Orgánica; 2015

CLAFQO

Chromones and its related compounds are relatively abundant in nature, and they actively participate in biological cycles of plants. Particularly, 2-trifluoromethylchromones are of great interest because of their biological and medicinal importance since they act as antispasmodics, bronchodilators and also have high antiviral,1 antifungal,2,3 biocide,4 antitumor6 and antimutagenic5 activity. Furthermore, ureides are also used as anticonvulsants, analgésics,7 antimicrobial8 and antiviral9 agents, etc.3-(2,2,2-trifluoro-acetyl) -1- (4-oxo-2-trifluoromethyl-4H-chromen-6-yl) urea was synthesized from 6-amino-2-trifluorometilcromona and trifluoroacetyl isocyanate as part of a project to prepare ureides from trifluorometilcromonas substituted with an NH2 group. The presence of the -CF3 group increases the reactivity of the chromones against different nucleophilic substrates, to provide a compound with increased biological properties.The novel ureide was characterized by vibrational (IR, Raman), UV?Vis and NMR (1H), spectroscopy and MS spectrometry. The molecular structure in the solid was determined by X-ray diffraction methods (see figure). The compound crystallizes in the triclinic P-1 space group with a=4.9861(5) Å, b=10.849(2) Å, c=13.541(2) Å, α=70.158(12)°, β=84.092(9)°, γ=88.774(10)°, and Z=2 molecules per unit cell. The molecular geometry of minimum energy obtained from theoretical calculations has C1 symmetry with values for the dihedral angles: C6-N1-C11-N2 180 ° and C7-C6-N1-C11 0 º. This molecule exhibits an extended planarity that involves both rings and the urea group. The vibrational, electronic and NMR, spectra were discussed and assigned with the assistance of DFT calculations.