G. Ahumada, David Carrillo, C. Manzur
Dec 5, 2016
Citations
0
Influential Citations
13
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract The one-pot double condensation reaction of 2-thenoyltrifluoroacetone (2-TTA) with ethylendiamine or o -phenylenediamine, in a 2:1 stoichiometric molar ratio, leads to the formation of 7-(thiophene-2-yl)-5-(trifluoromethyl)-2,3-dihydro-1 H -1,4-diazepine 2 and 2-thiophene-4-trifluoromethyl-1,5-benzodiazepine 3 , that were isolated in 56 and 53% yields, respectively. The bis (trifluoroacetamide)ethylene derivative 1 was also isolated in 32% yield as a side-product in the reaction of 2-TTA and ethylenediamine. Compounds 1 – 3 were fully characterized by elemental analysis, FT-IR and multinuclear ( 1 H, 13 C and 19 F) NMR spectroscopy. In addition, their molecular identities and geometries have been authenticated by single-crystal X-ray diffraction analysis. The spectroscopic and structural data confirm that the 1,4-diazepine 2 and the 1,5-benzodiazepine 3 exist in the imine-enamine and diimine tautomeric forms, respectively, both in solution and in the solid-state.