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 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
Please use this identifier to cite or link to this item http://hdl.handle.net/10773/20935

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.
Rachedi, Yahia
Hamdi, Maamar
Talhi, Oualid
Almeida, Filipe A.
Silva, Artur S. M.
Fadila, Balegroune
Malika, Hamadene
Kamel, Taibi
keywords: 1,3,5-TRISUBSTITUTED PYRAZOLES
REGIOSELECTIVE SYNTHESIS
BENZODIAZEPINES
CHALCONES
AMINES
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.
URI: http://hdl.handle.net/10773/20935
ISSN: 0022-2860
publisher version/DOI: http://doi.org/10.1016/j.molstruc.2013.12.082
source: JOURNAL OF MOLECULAR STRUCTURE
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2D-NMR X-ray crystallography and theoretical studies of the reaction mechanism for the synthesis of 15-benzodiazepines from dehydroacetic acid derivatives and o-phenylenediamines_10.1016j.molstruc.2013.12.082.pdf452.81 kBAdobe PDFview/open
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