1091619-53-2

Basic information

• Product Name: 2,3-dihydro-2-propylquinazolin-4(1H)-one
• Synonyms: 2,3-dihydro-2-propylquinazolin-4(1H)-one
• CAS NO: 1091619-53-2
• Molecular Weight: 190.245
• Mol File: 1091619-53-2.mol

Chemical Properties

• CAS DataBase Reference: 2,3-dihydro-2-propylquinazolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dihydro-2-propylquinazolin-4(1H)-one(1091619-53-2)
• EPA Substance Registry System: 2,3-dihydro-2-propylquinazolin-4(1H)-one(1091619-53-2)

Safety Data

• Hazardous Substances Data: 1091619-53-2(Hazardous Substances Data)

Upstream product

• 123-72-8 butyraldehyde 
• 28144-70-9 anthranilic acid amide 

Relevant articles and documents

Synthesis and characterization of copper(II) Schiff base complex supported on Fe3O4 magnetic nanoparticles: A recyclable catalyst for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones

Fe3O4-Schiff base of Cu(II) is found to be a recyclable and heterogeneous catalyst for the rapid and efficient synthesis of various 2,3-dihydroquinazolin-4(1H)-one derivatives from the two-component condensation of 2-aminobenzamide and an aldehyde. This reaction is simple, green and cost-effective. Separation and recycling can also be easily done by magnetic decantation of the Fe3O4 nanoparticles with an external magnet. The prepared catalyst was characterized using thermogravimetry, Fourier transform infrared spectroscopy, vibrating sample magnetometry, inductively coupled plasma analysis, X-ray diffraction and scanning electron microscopy.

Efficient preparation of boehmite silica dopamine sulfamic acid as a novel nanostructured compound and its application as a catalyst in some organic reactions

A novel type of recoverable boehmite nanocatalyst was prepared via immobilization of dopamine on the surface of boehmite followed by coating with silica and reacting with chlorosulfunic acid to obtain boehmite silica dopamine sulfamic acid (boehmite-Si-DSA). This compound was characterized by FT-IR spectroscopy, TGA, XRD, TEM and SEM techniques. Boehmite-Si-DSA was used as an efficient, recoverable and thermally stable heterogeneous nanocatalyst for the preparation of 2,3-dihydroquinazolin-4(1H)-one, sulfoxides and disulfides. The catalyst was recovered by simple filtration and reused several times without significant loss of catalytic efficiency.

Synthesis of copper (II)-supported magnetic nanoparticle and study of its catalytic activity for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones

A magnetic nanoparticle supported efficiently catalyzes for condensation 2-aminobenzamide with aldehydes to afford the corresponding 2,3- dihydroquinazolin-4(1H)-one derivatives successfully in high yield. The reactions were carried out in ethanol under reflux conditions. The protocol proves to be efficient and versatile benign in terms of very easy work-up and reused seven times without significant loss of catalytic activity. The heterogeneous catalyst was characterized by FT-IR spectroscopy, thermogravimetric (TGA) analysis, powder X-ray diffraction (XRD), scanning electron microscopy (SEM) and transmission electron microscope (TEM).

The novel acid-base magnetic recyclable catalyst prepared through carbon disulfide trapping process: Applied for green, one-pot, and efficient synthesis of 2,3-dihydroquinazolin-4 (1H) -ones and bis(indolyl)methanes in large-scale

Herein, a nano acid-base catalyst using magnetic core and carbamodithioic acid functional group have been synthesized and characterized. Its efficiency in the synthesis of dihydroquinazolinones and bis(indolyl)methanes derivatives was investigated. This novel metal-free catalyst exhibited significant catalytic activity in both reactions under green and mild reaction conditions (the yield obtained for the first reaction products: 82–98 % and for the second one: 61–97 %). The catalyst displayed good recyclability with no significant loss of catalytic activity after eight runs (the conversion of the eighth run was found as 83 %, the fresh catalyst conversion was 95 %). The introduced approach is attractive due to its applicability in the large-scale synthesis of important medicinal compounds.

Synthesis and characterization of VO–vanillin complex immobilized on MCM-41 and its facile catalytic application in the sulfoxidation reaction, and synthesis of 2,3-dihydroquinazolin-4(1H)-ones and disulfides in green media

In this work, a vanillin complex is immobilized onto MCM-41 and characterized by FT-IR, X-ray diffraction, scanning electron microscopy, energy dispersive spectroscopy, thermogravimetric analysis, and BET techniques. This supported Schiff base complex was found to be an efficient and recoverable catalyst for the chemoselective oxidation of sulfides into sulfoxides and thiols into their corresponding disulfides (using hydrogen peroxide as a green oxidant) and also a suitable catalyst for the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in water at 90°C. Using this protocol, we show that a variety of disulfides, sulfoxides, and 2,3-dihydroquinazolin-4(1H)-one derivatives can be synthesized in green conditions. The catalyst can be recovered and recycled for further reactions without appreciable loss of catalytic performance.

BF3-grafted Fe3O4@Sucrose nanoparticles as a highly-efficient acid catalyst for syntheses of Dihydroquinazolinones (DHQZs) and Bis 3-Indolyl Methanes (BIMs)

Current paper represents immobilization of sucrose on the Fe3O4 core and grafting of boron trifluoride (BF3) onto the new surface. The catalytic activity of these nanoparticles was tested in syntheses of Dihydroquinazolinones (DHQZs) and Bis (3-Indolyl) Methanes (BIMs) as two fruitful pharmaceutical structures. Acidic capacity, FT-IR, XRD, VSM, TGA and SEM–EDX tests are carried out on such novel nanoparticles (NPs). Catalyst has shown more acidic capacity per one gram of NPs than sulfonated homologue which was reported previously.

One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies

A metal-free and oxidant-free method for the one-pot preparation of quinazolin-4(3H)-ones enabled by electrochemical oxidation is described. Together with 2-aminobenzamides, a variety of aldehydes were successfully applied to an acid-catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline-4(3H)-ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin-4(3H)-ones, the synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib. (Figure presented.).

Synthesis, in silico study and cholinesterases inhibition activity of 2-substituted 2, 3-dihydroquinazolin-4(1H)-one derivatives

We have synthesized and evaluated a number of 2, 3-dihydroquinazolin-4(1H)-one derivatives as inhibitors of cholinesterases. In vitro assay results revealed that all synthesized compounds are active against both acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes and few compounds having longer alkyl chain at C-2 position showed better inhibition activity than standard drug galantamine. Moreover, bromo derivatives 6a-d were more active than nitro 5a-d and their un-substituted counterparts 4a-d. Amongst all, compound 6d, with IC50 values of 4.8±1.01 μM (AChE) and 11.1±1.15 μM (BChE) can be considered as good cholinesterase (AChE/BChE), inhibitor with greater selectivity towards BChE. In silico calculations revealed that all compounds have good pharmacokinetic profile along with having high probabilities for penetration across blood brain barrier (BBB), human intestinal absorption (HIA), non-AMES toxicity and non-carcinogenicity except nitro substituted derivatives which were predicted to show AMES toxicity. The synthesized compounds may lead toward development of new potent cholinesterase inhibitors.

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.

Heterogeneous Cu(II)/l-His@Fe3O4 nanocatalyst: A novel, efficient and magnetically-recoverable catalyst for organic transformations in green solvents

A novel, efficient and green Cu(ii)/l-His@Fe3O4 catalyst has been applied successfully in the synthesis of heterocyclic compounds. The resulting catalyst was used in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, polyhydroquinolines and 2-amino-6-(arylthio)pyridine-3,5-dicarbonitriles as biologically interesting compounds. The present research is focused on investigation of recycling, reusability and stability of the catalyst in phase reactions. The Cu(ii)/l-His@Fe3O4 catalyst was used at least six times with comparable activities to that of fresh catalyst. The chemical composition and the structure of the catalyst were analysed by TGA/DTG, EDS, XRD, VSM, FT-IR and SEM.