Synlett 2017; 28(17): 2247-2252
DOI: 10.1055/s-0036-1590306
letter
© Georg Thieme Verlag Stuttgart · New York

Dibenzo[b,e][1,4]diazepin-1-ones and their Ring-Opened Derivatives: Revisited Synthesis, 2D NMR and Crystal Structure

Brahim Cherfaouia, Houria Lakhdaria, b, Norah Bennamane*a, Rachid Ameraouib, Oualid Talhi*b, c, Filipe A. Almeida Pazd, Khaldoun Bacharib, Gilbert Kirsche, Kolli Nejar-Bellaraa, Artur M. S. Silva*c
  • aLaboratoire de Chimie Organique Appliquée, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediène, BP 32, El-Alia Bab-Ezzouar, 16111 Alger, Algeria   Email: noraoussaid@yahoo.fr
  • bCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques CRAPC, BP 384, Bou-Ismail-RP, 42004 Tipaza, Algeria
  • cQOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal   Email: artur.silva@ua.pt   Email: oualid.talhi@ua.pt
  • dCICECO – Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
  • eLaboratoire Structure et Réactivité des Systèmes Moléculaires Complexes, UMR 7565, Université de Lorraine, Avenue du Général Delestraint, Metz, France
Thanks are due to University of Aveiro and FCT/MEC for financial support to the QOPNA research project (FCT UID/QUI/00062/2013) and to the CICECO-Aveiro Institute of Materials (POCI-01-0145-FEDER-007679; FCT UID/CTM/50011/2013), financed by national funds and when appropriate co-financed by FEDER under the PT2020 Partnership Agreement, and to the Portuguese NMR Network. We would like also to thank FCT/MEC and the General Directorate for Scientific Research and Technological Development – DGRSDT of Algeria and Agence Thématique de Recherche en Sciences et Technologie ATRST for approving the co-financed bilateral project PT-DZ/0005. We further wish to thank CICECO for funding the purchase of the single-crystal X-ray diffractometers.
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Publication History

Received: 02 May 2017

Accepted after revision: 21 May 2017

Publication Date:
13 July 2017 (eFirst)

Abstract

The synthesis of 2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-ones was revisited and a catalyst-free method was established, by exploring the reactivity of 3-[(2-aminoaryl)amino]dimedones towards carbonylated electrophiles. 2D NMR and single-crystal X-ray diffraction studies were used to characterize the structures unequivocally and to review the mechanism leading to the formation of supposed positional isomers. The action of 3-[(2-aminoaryl)amino]dimedones on chromene-3-carboxylic acid, fumaryl, and oxalyl chloride has led to dibenzo[b,e][1,4]diazepin-1-one ring opening to produce novel Z-configured enaminone and linear diamides.

Supporting Information