Beilstein J. Org. Chem.2014,10, 2594–2602, doi:10.3762/bjoc.10.272
Chemistry, University of Debrecen, H-4010 Debrecen, Hungary Porfirin Ltd., Mikszáth K. u. 7. III/3, 4032 Debrecen, Hungary 10.3762/bjoc.10.272 Abstract Condensed O,N-heterocycles containing tetrahydro-1,4-benzoxazepine and tetrahydroquinoline moieties were prepared by a regio- and diastereoselective domino
Knoevenagel–[1,5]-hydride shift cyclization reaction of a 4-aryl-2-phenyl-1,4-benzoxazepine derivative obtained from flavanone. The relative configuration of products were determined by the correlation of 3JH,H coupling data with the geometry of major conformers accessed by DFT conformational analysis
cellular injuries in human neuroblastoma SH-SY5Y cells in the range of those of positive controls.
Keywords: 1,4-benzoxazepine; diastereoselective domino Knoevenagel–[1,5]-hydride shift cyclization; neuroprotective; tert-amino effect; TDDFT-ECD calculation; Introduction
The 1,4-benzoxazepine structural
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Graphical Abstract
Figure 1:
Pharmacologically active derivatives 1–4 containing the 1,4-benzoxazepine moiety or its analogue.