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|title: ||2D-NMR, X-ray crystallography and theoretical studies of the reaction mechanism for the synthesis of 1,5-benzodiazepines from dehydroacetic acid derivatives and o-phenylenediamines|
|authors: ||Rabahi, Amal|
Hamdi, Safouane M.
Almeida, Filipe A.
Silva, Artur S. M.
|keywords: ||1,3,5-TRISUBSTITUTED PYRAZOLES|
|issue date: ||2014|
|publisher: ||ELSEVIER SCIENCE BV|
|abstract: ||The synthesis of 1,5-benzodiazepines by the reaction of o-phenylenediamines (o-PDAs) with dehydroacetic acid DHAA [3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one] or conjugate analogues is largely reported in the literature, but still with uncontrolled stereochemistry. In this work, a comprehensive mechanistic study on the formation of some synthesized 1,5-benzodiazepine models following different organic routes is established based on liquid-state 2D NMR, single-crystal X-ray diffraction and theoretical calculations allowing the classification of two prototropic forms A (enaminopyran-2,4-dione) and B (imino-4-hydroxypyran-2-one). Evidences are presented to show that most of the reported 1,5-benzodiazepine structures arising from DHAA and derivatives preferentially adopt the (E)-enaminopyran-2,4-diones A. (C) 2014 Elsevier B.V. All rights reserved.|
|publisher version/DOI: ||http://doi.org/10.1016/j.molstruc.2013.12.082|
|source: ||JOURNAL OF MOLECULAR STRUCTURE|
|appears in collections||CICECO - Artigos|
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