Dibenzo[b,f][1,4]thiazepin-11-yl-diethyl-amine

Abstract

In the title compound, C17H18N2S, the thia­zepine ring adopts a boat conformation and the dihedral angle between the benzene rings is 75.92 (5)°, resulting in a butterfly-like conformation. In the crystal, mol­ecules are connected via weak Caromatic—H⋯N contacts involving the imine N atom as acceptor and through a quite short C—H⋯π inter­action. The resulting mol­ecular chains propagate along the c-axis direction.

Dibenzothiazepine Based MCR Chemistry

“…[18] We performed a data mining on the Cambridge Structural database (CSD) [63] on the solid-state characterization of this tricyclic scaffold, demonstrating that its overall shape is defined by both the conformation of the seven-membered ring and the relative arrangement of the fused aromatic rings. [17,18] In addition, we noticed that the tricyclic ring folding is influenced by the atom X (Figure 3, X = C, N, O, S). [5] Finally, dihedral angles R 1 16À N14À C13À C12 and R 2 17À C15À C3À C2 were taken into account revealing a relative planar conformation (see SI).…”

“…The unusual conformational equilibrium, which has been reported multiple times, [4,5,17–19] affords atropisomers. Those atropisomers, which depend on the substitution pattern can have high energy interconversion and can be separated, are non‐superimposable mirror images thus, enantiomers.…”

“…Understanding the conformational behavior of the dibenzothiazepines is the key to clarify the way that these species behave on a molecular level and subsequently to better understand their interactions with a biological target [18] . We performed a data mining on the Cambridge Structural database (CSD) [63] on the solid‐state characterization of this tricyclic scaffold, demonstrating that its overall shape is defined by both the conformation of the seven‐membered ring and the relative arrangement of the fused aromatic rings [17,18] . In addition, we noticed that the tricyclic ring folding is influenced by the atom X (Figure 3, X=C, N, O, S) [5] .…”

“…[4,5] Many commercial drugs consist of a benzothiazepine core, including quetiapine, metiapine and clotiapine with an antipsychotic mechanism of action [6][7][8][9] and bioactive compounds [2,3] such as Ca 2 + channel blockers, [10] antiviral, [11,12] antimicrobial, [13] antifungal, [14] histone deacetylase 6 (HDAC6) inhibitors [15] and even molecules with interesting electronic properties (Figure 1C). [16] The unusual conformational equilibrium, which has been reported multiple times, [4,5,[17][18][19] affords atropisomers. Those atropisomers, which depend on the substitution pattern can have high energy interconversion and can be separated, are non-superimposable mirror images thus, enantiomers.…”