Beilstein J. Org. Chem.2023,19, 700–718, doi:10.3762/bjoc.19.51
frameworks with dibenzo[b,f]azepine derived ligands have also been reported. This review provides a brief overview of the different synthetic strategies to dibenzo[b,f]azepines and other dibenzo[b,f]heteropines.
Keywords: dibenzo[b,f]azepine; dibenzo[b,f]heteropine; dibenzo[b,f]oxepine; iminostilbene
to 5H-dibenzo[b,f]azepine (1a)
10,11-Dihydro-5H-dibenzo[b,f]azepine (2a), also known as iminobibenzyl (2a), is used as precursor for several compounds, including 5H-dibenzo[b,f]azepine (iminostilbene) (1a), and therefore will be discussed in a section on large scale industrial synthesis.
While
) by alkylation of 1a was patented in 1997 [79]. The process involves the alkylation of iminostilbene (1a) as a critical intermediate step (Scheme 33C). The alkyl halide linker of 148 was further functionalised by reaction with piperazine derivative 149 to give opipramol (5).
6.2 C-Functionalisation
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Graphical Abstract
Figure 1:
Dibenzo[b,f]azepine (1a), -oxepine (1b) and -thiepine (1c) as examples of dibenzo[b,f]heteropines (1...