950-31-2

Usage

Chemical class

Spiro compounds

Spiro ring structure

Comprises a cyclohexane and quinazolinone moiety

Biological activities

Studied for antifungal and antibacterial properties

Potential pharmaceutical applications

Has potential as a scaffold for the development of novel drugs

Medicinal chemistry applications

Has been the subject of research for its potential use in drug discovery and development

Versatility

Interesting compound for further exploration in the field of drug discovery and development due to its unique spiro ring structure.

Upstream product

• 118-48-9 isatoic anhydride 
• 108-94-1 cyclohexanone 
• 96447-10-8 spiro<2H-3,1-benzoxazine-2,1'-cyclohexan>-4(1H)-one 
• 77287-34-4 formamide 
• 612-24-8 o-nitrobenzonitrile 
• 108-91-8 cyclohexylamine 
• 28144-70-9 anthranilic acid amide 
• 108-93-0 cyclohexanol 
• 56814-11-0 anthranilic acid cyclohexylamine 
• 2043-61-0 cyclohexanecarbaldehyde 
• 120-92-3 cyclopentanone 
• 1885-29-6 anthranilic acid nitrile 
• 1904-58-1 anthranilic acid hydrazide 
• 610-15-1 2-nitrobenzamide 

Downstream Products

• 126492-27-1 C₂₂H₂₂Cl₂N₂O₂S 
• 126492-26-0 C₂₂H₂₄N₂O₂S 
• 126492-31-7 C₂₁H₂₀Cl₂N₂O₂ 
• 126492-30-6 C₂₁H₂₂N₂O₂ 
• 80477-97-0 3-acetyl-1-(1-cyclohexenyl)-2-methyl-1,2,3,4-tetrahydroquinazolin-4-one 
• 80477-96-9 1-(1-cyclohexenyl)-2-methyl-1,2,3,4-tetrahydroquinazolin-4-one 
• 91972-78-0 Cyclohexyl-2-carbamoyl-cyclohexyl-amin 
• 126492-23-7 C₁₃H₁₆N₂S 
• 80477-93-6 2-acetonylidene-1-(1-cyclohexenyl)-1,2,3,4-tetrahydroquinazolin-4-one 
• 80477-92-5 1-(1-cyclohexenyl)-2-methyl-1,4-dihyroquinazolin-4-one 

Relevant academic research and scientific papers

Basic ionic liquid as catalyst and surfactant: green synthesis of quinazolinone in aqueous media

Basic imidazolium-based ionic liquids not only possess the extraordinary physicochemical properties of ionic liquids, but also have excellent basicity and surfactivity. 1-Propyl-3-alkylimidazole hydroxide ionic liquids ([PRIm][OH]) were synthesized and their catalytic and surfactant behavior were studied in this work. [PRIm][OH] owned excellent surfactivity, and their alkyl chains and ion pairs benefit hydrophobicity and hydrophilicity respectively. The surfactivity of [PRIm][OH] increased with increasing alkyl chain length. [PRIm][OH] showed better catalytic performance than NaOH in the condensation of 2-aminobenzonitrile with cyclohexanone in aqueous medium, and the catalytic performance was well coincident with their surfactant behavior. [PRIm][OH] could decrease the interfacial tension of solvent effectively and form micelles in water. The formed micelles could solubilise more reactants into water and effectively increase the chance of contact between reactants and catalytic active sites. The catalyst dosage obviously affected catalytic performance. The catalytic system is a promising recyclable system.

Probing the catalytic activity of highly efficient sulfonic acid fabricated cobalt ferrite magnetic nanoparticles for the clean and scalable synthesis of dihydro, spiro and bis quinazolinones

An exceptionally productive, rapid, simple, and eco-friendly approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been developed utilizing acidic magnetically retrievable cobalt ferrite nanoparticles (CFNP@SO3H). Herein, we have demonstrated the synthesis of these profoundly demanding N-heterocyclic molecules within 3-10 min in excellent yields at room temperature using the environmentally benign solvent ethanol. Outstanding catalytic performance, ease of retrievability, high turnover frequency (TOF) values (197.13-403.23 h?1), admirable green chemistry metrices, such as theEfactor (0.10), reaction mass efficiency (RME) value (90.9%), carbon efficiency (100%) and atom economy (AE) value (92.6%), and reusability for up to six runs without a significant loss of activity, make the current methodology advantageous from an environmental, as well as industrial perspective.

Heterocyclic reaction inducted by Br?nsted–Lewis dual acidic Hf-MOF under microwave irradiation

Use of green chemistry and alternative strategies has been explored to prepare diverse organic derivatives. The combination between heterogeneous catalyst, environmentally benign reaction and high-yielding methods is gaining momentum. Herein, a defective 6-connected Hf-MOF, named Hf-BTC, was efficiently synthesized and characterized for the heterogeneous catalysis under microwave irradiation. The MOF features including structural defect, porosity, acidity, and stability was analyzed by powder X-ray diffraction, N2 sorption isotherms, acid-base titration, and thermal gravimetric analysis. In the catalytic studies, the Br?nsted-Lewis dual acidic Hf-BTC was efficiently applied for the synthesis of the heterocyclic compounds via the microwave-assisted cycloaddition and condensation reactions. The reactions proceeded smoothly in the presence of the Hf-MOF with a broad scope of substrates provided the expected products in high to excellent yields (up to 99 %) for few minutes and the catalyst could be easily recycle over many consecutive reactions without loss of its reactivity and structure.

Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2′-Hydroxyaryl Ketones and 2-Aminobenzamides with Simple Amines

The cationic Ru–H complex [(C6H6)(PCy3)(CO)RuH]+BF4– (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone (L1) was found to be a highly effective catalyst for the deaminative coupling reaction of 2′-hydroxyaryl ketones with simple amines to form 3-substituted flavanone products. The analogous deaminative coupling reaction of 2-aminobenzamides with branched amines directly formed 3,3-disubstituted quinazolinone products. The catalytic method efficiently installs synthetically useful flavanone and quinazolinone core structures without employing any reactive reagents.

Sustainable parts-per-million level catalysis with FeIII: One-pot cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water

A silica-supported iron complex has been identified as a highly active and reusable catalyst for the synthesis of medicinally important 2,3-dihydroquinazolin-4(1H)-ones. The catalyst was fully characterized by various spectroscopic analyses such as Fourie

Gemini basic ionic liquid as bi-functional catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones at room temperature

A cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones has been developed from 2-aminobenzonitriles and carbonyl analogues using Gemini basic ionic liquid as green catalyst cum solvent at room temperature. Both aldehydes and ketones were condensed with 2-aminobenzonitriles affording good to excellent yields of products. Moreover, the ionic liquids can be reused up to 5th cycle without significant loss of catalytic activity.

Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in the presence of Fe3O4@nano-cellulose–OPO3H as a bio-based magnetic nanocatalyst

In this research, we have used Fe3O4@nano-cellulose–OPO3H as magnetic bio-based nanocatalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones via condensation of 2-aminobenzamide and different aldehydes. The major advantages of the present methodology are good yields, ecofriendly catalyst, and easy workup.

A Br?nsted Acid Ionic Liquid Immobilized on Fe3O4?SiO2 Nanoparticles as an Efficient and Reusable Solid Acid Catalyst for the Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Abstract: In the present study, an efficient and magnetically recoverable Br?nsted acid ionic liquid, 1-methyl-3-[3-(triethoxysilyl)propyl]-1H-imidazol-3-ium hydrogen sulfate, immobilized on the surface of Fe3O4?SiO2 magnetic nanoparticles (Fe3O4?SiO2–ImHSO4) has been used for a high-yield synthesis of 2,3-dihydroquinazolin-4(1H)-ones through the condensation of anthranilamide with aldehydes and ketones in EtOH at room temperature or under reflux. The significant features of the present protocol are short reaction times, high yields of products, ecofriendly reaction conditions, simple work-up, and reusability of the catalyst. The catalyst can be simply magnetically recovered and reused at least five times without considerable loss of its catalytic activity.

Preparation of choline sulfate ionic liquid supported on porous graphitic carbon nitride nanosheets by simple surface modification for enhanced catalytic properties

Supported ionic liquids (SILs) have attracted rising interest and the subject of active research in the last decades due to the diversified range of applications and yet reports on ILs is still rapidly increasing. This work reports a choline sulfate ionic liquid supported on fascinating and highly stable porous graphitic carbon nitride (g-C3N4) nanosheets as an inexpensive and an environmentally friendly reusable ionic catalyst in organic synthesis typically requiring a harmful organic solvent and highly toxic acids. g-C3N4?SO3Ch was prepared by mixing sulfonic acid functionalized graphitic carbon nitride nanosheets (g-C3N4?SO3H) with choline hydroxide or via a novel approach. The introduction of a choline sulfate could significantly enlarge specific surface areas with rich reaction sites and suppressed the recombination of sheets. This work provides a new way to improve the chemical property of g-C3N4 along with the recyclability of the ionic liquid. g-C3N4?SO3Ch (IL/g-C3N4) offers an effective, reusable, inexpensive, environmentally friendly and low-cost catalyst for the synthesis of 3,4-dihydropyrimidin-2 (1H)-ones, 2,3-dihydroquinazolin-4 (1H)-ones and bisindolylmethanes in good to excellent yields. The prepared catalyst synthesized compounds were well characterized by different techniques such as FT-IR, XRD, SEM, EDX and TGA.

Effect of Fe(iii)-based MOFs on the catalytic efficiency of the tandem cyclooxidative reaction between 2-aminobenzamide and alcohols

The catalytic properties of metal-organic frameworks (MOFs) containing triangular Fe(iii) clusters in the promotion of organic syntheses and photocatalysis applications have been receiving substantial attention for decades. These clusters are appealing due to the strong Lewis acidity afforded by coordinatively unsaturated sites upon the removal of solvent from the framework. In this paper, triangular Fe(iii) cluster-based MOFs were shown to be highly efficient heterogeneous catalysts for the solvent-free one-pot condensation of 2-aminobenzamide and alcohols to form quinazolin-4-ones under microwave irradiation. The Fe-MOF catalysts ranging from microporous to mesoporous structures with a variety of geometrical pore structures were investigated. Because of the open accessible spaces for reactants and high density of active sites, MOF-907, built from trimer Fe clusters and a mixture of two linkers, was more effective than other Fe(iii)-MOFs. The catalyst can be used for a broad substrate scope and recycled several times without a significant drop-off in its activity.