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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

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Resumo: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.
Autores principais:Rabahi, Amal
Outros Autores:Hamdi, Safouane M.; Rachedi, Yahia; Hamdi, Maamar; Talhi, Oualid; Almeida, Filipe A.; Silva, Artur S. M.; Fadila, Balegroune; Malika, Hamadene; Kamel, Taibi
Assunto:1,3,5-TRISUBSTITUTED PYRAZOLES REGIOSELECTIVE SYNTHESIS BENZODIAZEPINES CHALCONES AMINES
Ano:2014
País:Portugal
Tipo de documento:artigo
Tipo de acesso:acesso restrito
Instituição associada:Universidade de Aveiro
Idioma:inglês
Origem:RIA - Repositório Institucional da Universidade de Aveiro

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