Related Experiment Video
Updated: Jun 27, 2026
10:42
Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
The 1,5-Benzodiazepin-2-Ones: A Review on Synthetic Strategies, Reactivity and Functional Applications
Hasan Mtiraou1, Ameni Ghabi1, Hanan Al-Ghulikah2
1Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/CHPNR, Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5000, Tunisia.
Molecules (Basel, Switzerland)
|June 26, 2026
Summary
1,5-Benzodiazepin-2-ones are versatile heterocyclic compounds with diverse applications. This review details their synthesis, reactivity, and uses in medicinal chemistry, corrosion inhibition, and materials science.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Materials Science
Background:
- 1,5-Benzodiazepin-2-ones are significant heterocyclic compounds.
- They possess versatile scaffolds and multifunctional properties due to their fused benzene-diazepine core.
- These characteristics make them valuable in fundamental and applied research.
Purpose of the Study:
- To provide a comprehensive overview of 1,5-benzodiazepin-2-ones.
- To emphasize diverse synthetic methodologies, reaction mechanisms, and structure-property relationships.
- To summarize applications in medicinal chemistry, corrosion inhibition, and photoluminescent materials.
Main Methods:
- Review of classical and modern synthetic approaches.
- Discussion of condensation reactions, multicomponent processes, and catalytic methods.
- Inclusion of green chemistry approaches and sustainable protocols.
Main Results:
- The intrinsic reactivity allows access to structurally diverse derivatives.
- Demonstrated significant biological activities in medicinal chemistry.
- Applications shown in corrosion inhibition and photoluminescent materials.
Conclusions:
- 1,5-Benzodiazepin-2-ones are crucial scaffolds with broad utility.
- Advances in synthesis have led to more efficient and sustainable protocols.
- Future research should focus on further development and application of these systems.
Keywords:
1,5-benzodiazepin-2-oneN-heterocyclesbenzodiazepinesmaterials chemistrymedicinal chemistrysynthesisMore Related Videos
Related Concept Videos
01:19Sedatives and Hypnotics Drugs: Benzodiazepines
Benzodiazepines have both sedative and hypnotic properties. They include compounds such as diazepam (Valium) and alprazolam (Xanax). Structurally, their cores are similar, consisting of the fusion of a benzene ring and a diazepine ring, but they share a common mechanism of action in the central nervous system (CNS).
Benzodiazepines work by enhancing the effects of the inhibitory neurotransmitter GABA. They bind to the GABAA receptor, increasing its affinity for GABA, which opens chloride...
Benzodiazepines work by enhancing the effects of the inhibitory neurotransmitter GABA. They bind to the GABAA receptor, increasing its affinity for GABA, which opens chloride...
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
01:29Anxiolytic Drugs: Benzodiazepines and Buspirone
Benzodiazepines are a class of anxiolytic drugs known for their rapid efficacy and high therapeutic-to-lethal dose ratio, but with a potential risk of drug dependence. These drugs are lipophilic, allowing for rapid absorption after oral administration, eventually reaching the central nervous system (CNS). Once in the CNS, benzodiazepines bind to the allosteric site of the GABAA receptor. This binding enhances the inhibitory effects of the neurotransmitter GABA. By doing so, they prevent...
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
01:13Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.