Synthesis, NMR Spectroscopy, and Molecular Modeling of2-Methyl-2,3,4,5-tetrahydro-1H-[1]benzothieno[2,3-c]azepine
2020
A new synthetic approach to fused azepines was demonstrated on an example of
the synthesis of 2-methyl-2,3,4,5-tetrahydro-1H-[1]benzothieno[2,3-c]azepine. The key stage of the synthesis is the formation of the
azepine ring under the Eschweiler–Clark reaction conditions. The Gibbs energy of
activation for the inversion of the azepine ring was determined by dynamic
1H NMR spectroscopy. Molecular modeling of the
structure and estimation of the 1H and
13C NMR chemical shifts were performed for
2-methyl-2,3,4,5-tetrahydro-1H-[1]-benzothieno[2,3-c]azepine. The magnetic shielding tensors were calculated by the
standard GIAO method using the B3LYP/6-31G(d,p)-optimized molecular geometry
parameters. The solvent effect was taken into account in the PCM approximation.
The calculated 1H and 13C
NMR chemical shifts of 2-methyl-2,3,4,5-tetrahydro-1H-[1]-benzothieno[2,3-c]azepine are in good agreement with the experimental values
observed in the spectra of its DMSO-d6 solution.
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