%0 Journal Article %T A facile access to new diazepines derivatives: Spectral characterization and crystal structures of 7-(thiophene-2-yl)-5-(trifluoromethyl)-2,3-dihydro-1H-1,4-diazepine and 2-thiophene-4-trifluoromethyl-1,5-benzodiazepine %+ Institut des Sciences Chimiques de Rennes (ISCR) %+ Universidad de Valparaiso [Chile] %A Ahumada, G. %A Carrillo, D. %A Manzur, C. %A Fuentealba, M. %A Roisnel, T. %A Hamon, J.-R. %Z Financial support from the Fondo Nacional de Desarrollo Científicoy Tecnologico [FONDECYT (Chile), grant no.1140903 (C.M. andD.C.)], FONDEQUIP [EQ (M130154) and EQ (M120095)] and theVicerrectoría de Investigacion y Estudios Avanzados, PontificiaUniversidad Catolica de Valparaíso, Chile (C.M. and D.C.), the CNRSand the Universite de Rennes 1 is gratefully acknowledged. Thisresearch has been performed as part of the Chilean-French InternationalAssociated Laboratory for “Inorganic Functional Materials”(LIAMIF-CNRS N836). The authors thank also Dr S. Sinbandhit(CRMPO, Rennes) for helpful assistance with NMR experiments.G.A. thanks the CONICYT (Chile) for a graduate fellowships, and Dr.C. W. Bielawski, University of Texas at Austin (USA) for his helpfuldiscussions and advices during his internship in that University. %< avec comité de lecture %@ 0022-2860 %J Journal of Molecular Structure %I Elsevier %V 1125 %P 781--787 %8 2016 %D 2016 %R 10.1016/j.molstruc.2016.07.047 %K Complexation %K Ethylene %K Nitrogen compounds %K Nuclear magnetic resonance spectroscopy %K Single crystals %K Spectrum analyzers %K Thiophene %K X ray diffraction analysis %K 2-thenoyltrifluoroacetone %K Benzodiazepine %K Diazepine %K Enamines %K Single crystal x-ray diffraction %K Condensation reactions %Z Chemical SciencesJournal articles %X 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-1H-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 (1H, 13C and 19F) 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. © 2016 Elsevier B.V. %G English %2 https://univ-rennes.hal.science/hal-01367194/document %2 https://univ-rennes.hal.science/hal-01367194/file/A%20facile%20access%20to%20new%20diazepines%20derivatives.pdf %L hal-01367194 %U https://univ-rennes.hal.science/hal-01367194 %~ UNIV-RENNES1 %~ CNRS %~ INSA-RENNES %~ ENSC-RENNES %~ ISCR %~ SCR-CD %~ ISCR-OMC %~ STATS-UR1 %~ UR1-SPM %~ ISCR-PRATS %~ INC-CNRS %~ UR1-UFR-SPM %~ UR1-HAL %~ UR1-SDLM %~ TEST-UNIV-RENNES %~ TEST-UR-CSS %~ UNIV-RENNES %~ INSA-GROUPE %~ UR1-MMS %~ TEST2-HALCNRS