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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 |
Author: | 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. |
Peer review: | yes |
URI: | http://hdl.handle.net/10773/20935 |
DOI: | 10.1016/j.molstruc.2013.12.082 |
ISSN: | 0022-2860 |
Publisher Version: | 10.1016/j.molstruc.2013.12.082 |
Appears in Collections: | CICECO - Artigos |
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