Highly diastereoselective synthesis of rigid 3-enamino-1,5-benzodiazepines

Abstract

A variety of new (3-Z)-3-((alkyl/aryl)aminomethylene)-4-(2-hydroxyphenyl)-1,3-dihydro-2H-1,5-benzodiazepin-2-ones were synthesized via addition of primary amines on the benzopyrano[4,3-c]-1H-1,5-benzodizepin-2one. High yields with excellent diastereoselectivity were obtained. The structure of cis-β-enamino-1,5benzodiazepine derivatives was characterized by 1D and 2D NMR and confirmed by an X-Ray diffraction analysis. All prepared compounds were evaluated for their in vitro antibacterial activities and promising results were given.

Synthesis of New Chiral Triazoles Linked 1,5‐Benzodiazepine Conjugates via Copper‐Catalyzed 1,3‐Dipolar Cycloaddition Reaction

“…The use of the azides 5 and the compounds 4 a – d as the key intermediates in the stereoselective synthesis of disubstituted 1,2,3‐triazoles linked‐1,5‐benzodiazepinones via a copper‐ catalyzed 1,3‐dipolar cycloaddition (Table 3) afforded 6 a – j and 7 a – j as two series [14] . Optimal conditions with a DCM/NEt 3 /CuI (5 mol %) at rt for 4 h give the access to the 1,4‐disubstitued 1,2,3,–triazoles 6 a – j and 7 a – j in moderate to good yields (78–95 %).…”

“…Indeed, the 4‐(2‐hydroxyphenyl)‐1,5‐benzodiazepin‐2‐one framework presents four usual reactive sites (Figure 2a). Thus, this high capacity of modulation allowed the introduction of an electronwithdrawing group with photoluminescence properties, [12a] an alkylidene substituent at the position 3, [14] or a triazolyl pendant arm on the nitrogen of the lactam function [12b] (Figure 2b). As a continuation of our ongoing efforts directed toward the preparation of compounds more effective toward benzodiazepine or adenosine receptor binding [10] by the introduction of the 1,2,3‐triazole derivatives as substituents on the BZD ring system, we wished expand the range of the molecular diversity of these BZD.…”

Regiospecific Synthesis and Structural Studies of 3,5-Dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-ones and Comparison with 1,3-Dihydro-2H-benzo[b][1,4]diazepin-2-ones

“…Several papers on benzo­[ b ]­[1,4]­diazepines have been published and these encompass new synthetic methodologies − and reactivity studies, including a comprehensive review and a more recent reference . The biological properties of benzo­[ b ]­[1,4]­diazepinones closely related to our work have been reported and the compounds are potent noncompetitive metabotropic glutamate receptor antagonists .…”

Synthesis, Characterization, and Biological Activity of Mixed ligand Complexes from 8-Hydroxyquinoline and new Ligand for β-Enaminone

“…Enaminones produced from β -carbonyl molecules are relatively stable, most likely owing to ketoenol and imine-enamine tautomeric equilibrium [4] (Figure 1). Notably, the structure of the molecule shows that there is a strong intramolecular hydrogen bond along the heterodienic O=C-C=C-NH moiety, which takes the shape of a six-membered ring and makes the structure stiffer [5] .…”

“…Figure 1: Tautomeric equilibria of βenaminones. 5,5-dimethylcyclohexane-1,3-dione, is an organic compound that belongs to the cyclic ß-diketones type [6] . These white to light yellow crystalline are also known as methone, dimethyldihydroresorcinol, and cyclomethone.…”