A monoclinic modification of (4Z)-1-benzyl-4-(2-oxopropylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Abstract

In the title molecule, C19H18N2O2, the orientation of the oxopropylidene substituent is largely determined by an intramolecular N—H...O hydrogen bond. In the crystal, C—H...O hydrogen bonds form zigzag chains, which are elaborated into sheets lying parallel to (101) by complementary C—H...π interactions. Comparisons to the structure of the triclinic modification are made.

(3R,4Z)-1,3-Diethyl-4-(2-oxopropylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

“…1,4-and 1,5-Benzodiazepines are commonly used as anxiolytic and anticonvulsive drugs: these effects are primarily mediated via the benzodiazepine receptors located in the central nervous system (Tallman et al, 1980). In a continuation on our studies (Sebhaoui et al, 2017;Samba et al, 2018) of benzodiazepine derivatives, we report here the alkylation of (4Z)-4-(2-oxopropylidene)-2,3,4,5-tetrahydro-1,5-benzodiazepin-2-one with ethyl iodide under solid-liquid phase-transfer catalytic conditions leading to the title compound.…”