31785-60-1

Basic information

• Product Name: 1-(naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one
• CAS NO: 31785-60-1
• Molecular Formula: C₁₈H₁₄N₂O
• Molecular Weight: 274.3166
• Mol File: 31785-60-1.mol

Chemical Properties

• Boiling Point: 563.6°C at 760 mmHg
• Flash Point: 294.6°C
• Density: 1.257g/cm³
• Vapor Pressure: 1E-12mmHg at 25°C
• Refractive Index: 1.687
• CAS DataBase Reference: 1-(naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one(31785-60-1)
• EPA Substance Registry System: 1-(naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one(31785-60-1)

Safety Data

• Hazardous Substances Data: 31785-60-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one is used as a pharmaceutical agent for its diverse bioactivity, including anticancer, antifungal, and anti-inflammatory properties. Its unique structure allows it to target various biological pathways and mechanisms, offering potential therapeutic benefits in treating a range of diseases and conditions.
Used in Cancer Research:
In cancer research, NQDQ is utilized as an anticancer agent, where its bioactivity has shown potential in inhibiting the growth and proliferation of cancer cells. Its ability to target multiple cellular pathways makes it a promising candidate for further investigation into its anticancer properties and possible development as a therapeutic agent.
Used in Antifungal Applications:
NQDQ is also used as an antifungal agent, where its bioactivity has demonstrated effectiveness against various fungal species. This makes it a potential candidate for the development of new antifungal drugs to combat fungal infections.
Used in Anti-inflammatory Research:
In the realm of anti-inflammatory research, NQDQ is employed to study its potential to alleviate inflammation. Its demonstrated bioactivity in this area suggests that it could be a valuable component in the development of new anti-inflammatory medications.
Overall, the diverse applications of 1-(naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one across various fields of medicine highlight its potential as a versatile and promising compound for future pharmaceutical development.

Upstream product

• 66-77-3 1-naphthaldehyde 
• 28144-70-9 anthranilic acid amide 
• 118-48-9 isatoic anhydride 
• 631-61-8 ammonium acetate 
• 1885-29-6 anthranilic acid nitrile 

Relevant articles and documents

Potassium tert-Butoxide Promoted Synthesis of Dihydroquinazolinones

We herein report an efficient synthetic protocol to access heterocyclic dihydroquinazolinones by a transition-metal-free process, involving the reaction of 2-aminobenzonitriles with aldehydes in the presence of KOtBu. The method is compatible with aromatic ketones providing 2,2-disubstituted dihydroquinazolinones in high yields. This reaction proceeds feasibly at room temperature and features a broad substrate scope and tolerance to a range of functional groups. The mechanism follows a radical pathway.

A Facile Microwave and SnCl2Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones

An elegantly simple, facile, and robust approach to a scaffold of biological importance, 2,3-dihydroquinazolin-4(1H)-ones, is reported. A catalytic 1 % SnCl2/microwave-mediated approach afforded access to pure material, collected by cooling and filtration after 20-min microwave irradiation at 120°C. A total of 41 analogues were prepared in isolated yields of 17-99 %. This process was highly tolerant of aliphatic, aromatic, heterocyclic, and acyclic aldehydes, but furan, pyrrole, and thiophene aldehyde reactivity correlated with propensity towards electrophilic addition and/or Diels-Alder addition. As a result, thiophene afforded high yields (80 %) whereas pyrrole carboxaldehyde failed to react. With simple cinnamaldehydes, and in the SbCl3-mediated reaction, and with α,β-unsaturated aldehydes the equivalent quinazolin-4(3H)-ones, and not the 2,3-dihydroquinazolin-4(1H)-ones, was favoured.

Green and efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones and their anthelmintic studies

A facile and highly efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones derivatives has been developed by the condensation of anthranilamide with aldehydes using sulfonic acid functionalized l-Proline?Fe3O4 nanoparticles as a catalyst. The advantages of this protocol are easy recovery and reusability of the catalyst besides simple work-up procedure and short reaction time. In addition, the anthelmintic activities of some selective compounds were investigated and it was found that 2-phenyl-2,3-dihydroquinazolin-4(1H)-one exhibited profound anthelmintic activity against two helminth models.

Phosphotungstic acid mediated, microwave assisted solvent-free green synthesis of highly functionalized 2?-spiro and 2, 3-dihydro quinazolinone and 2-methylamino benzamide derivatives from aryl and heteroaryl 2-amino amides

Phosphotungstic acid has been found as green catalyst for the synthesis of spiro and cyclized quinazolinones and 2-amino substituted carboxamide under microwave irradiation and solvent-free condition has been developed. The scope of the reaction has been demonstrated for a variety of aldehydes and ketones with O-amino amides such as 2-amino-benzamide, 2-amino-5-iodo benzamide, 3-aminothiophene-2-carboxamide, 3-aminobenzofuran-2-carboxamide and 2-aminopyridine-3-carboxamides. The reaction afforded spiro-, cyclized quinazolinones and 2-amino substituted carboxamide derivatives within few minutes of irradiation in excellent yield. Plausible mechanism for the formation of products is provided. Synthetic utility of 1′H-spiro[fluorene-9,2′-quinazolin]-4′(3′H)-one 3a has been demonstrated by synthesis of 1,4-di(1′H-spiro[fluorene-9,2′-quinazolin]-4′(3′H)-one) buta-1,3-diyne 12, 1′-((1-benzyl-1H-1,2,3-triazol-4-yl) methyl)-1′H-spiro[fluorene-9,2′-quinazolin]-4′(3′H)-one 13 and 1′-phenyl-1′H-spiro[fluorene-9,2′-quinazolin]-4′(3′H)-one 14 under standard protocols.

Recyclable [Ce(l -Pro) 2 ] 2 (Oxa) used as Heterogeneous Catalyst: One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones in Ethanol

[Ce(l -Pro) 2 ] 2 (Oxa) was used as a recyclable heterogeneous catalyst under mild conditions for the preparation of 2-aryl-2,3-dihydroquinazolin-4(1 H)-one derivatives. The one-pot protocol proceeds in ethanol using anthranilamide with several aldehydes at 50-55 °C. The catalyst can be recycled and reused three cycles without significant loss of catalytic activity.

Method for synthesis of quinazolinone derivative

The invention discloses a method for synthesis of quinazolinone; the method comprises the steps of starting from o-aminobenzamide, taking water as a solvent, carrying out a ring-enlargement reaction with benzaldehyde, to generate a dihydroquinazolinone intermediate, and then under participation of a metal iridium complex, dehydrogenating to obtain the quinazolinone derivative; the reaction shows three remarkable advantages: 1) the reaction is carried out in an aqueous solution so as to reduce use of a large amount of organic solvents, and water is a cheap, green and safe solvent; 2) the reaction avoids use of highly toxic oxidants, so as to avoid damage to the environment; and 3) hydrogen gas generated from the reaction is a by-product, and has no environmental pollution; therefore, the reaction accords with the requirements of green chemistry, and has broad prospects for development.

Green protocol for synthesis of 2,3-dihydroquinazolin-4(1H)-ones: lactic acid as catalyst under solvent-free condition

Abstract: In the present work, lactic acid was used as novel, green catalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives via two distinct methods, including reaction of 2-aminobenzamide with aldehydes/ketones or isatoic anhydride with ammonium acetate and aldehydes in neat condition at 70?°C. The desired products were obtained in satisfactory yields. Short reaction time, easy workup, and more importantly environmental benignity are the most outstanding advantages of these procedures. Graphical Abstract: [Figure not available: see fulltext.]

3,3′-(butane-1,4-diyl)bis(1,2-dimethyl-1H-imidazol-3-ium) dibromide [BDBIm] Br-An efficient reusable ionic liquid for the microwave-assisted synthesis of quinazolinones

A series of 2-substituted quinazolin-4(1H)-ones have been synthesized in excellent yields and short reaction times by one-pot reaction of isatoic anhydride with ammonium acetate and aromatic aldehydes under microwave irradiation. The reaction was efficiently promoted by 0.5 mmol of 3,3′-(butane-1,4-diyl)bis(1,2-dimethyl-1H-imidazol-3-ium) dibromide [BDBIm] Br, and the catalyst could be recovered easily and reused without appreciable loss of reactivity.

Tandem supramolecular synthesis of substituted 2-aryl-2,3- dihydroquinazolin-4(1H)-ones in the presence of β-cyclodextrin in water

Substituted 2-aryl-2,3-dihydroquinazolin-4(1H)-ones were prepared for the first time in water under neutral conditions by the reaction of aniline, isatoic anhydride, and aldehyde mediated by β-cyclodextrin in good yields. β-Cyclodextrin can be recovered a

A concise aqueous phase supramolecular synthesis of 2-phenyl-2,3- dihydroquinazolin-4(1H)-one derivatives

2-Phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives were synthesized for the first time in water under neutral conditions by the reaction of aldehyde, and anthranilamide mediated by β-cyclodextrin in high yields. β-Cyclodextrin can be recovered and reused with a small loss of catalytic activity.