13165-35-0

Basic information

• Product Name: 7-chloroquinazoline-2,4(1H,3H)-dione
• Synonyms: 7-chloroquinazoline-2,4(1H,3H)-dione;7-Chloro-2,4-dioxo-1,2,3,4-tetrahydroquinazoline;NSC 60434;7-chloroquinazoline-2,4-diol 13165-35-0;7-CHLORO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-QUINAZOLINE;7-Chloroquinazoline-2,4(1H,3H)
• CAS NO: 13165-35-0
• Molecular Formula: C₈H₅ClN₂O₂
• Molecular Weight: 196.5905
• Mol File: 13165-35-0.mol
• Article Data: 53

Chemical Properties

• Melting Point: 360-362℃
• Appearance: /
• Density: 1.475g/cm³
• Refractive Index: 1.601
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.13±0.20(Predicted)
• CAS DataBase Reference: 7-chloroquinazoline-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloroquinazoline-2,4(1H,3H)-dione(13165-35-0)
• EPA Substance Registry System: 7-chloroquinazoline-2,4(1H,3H)-dione(13165-35-0)

Safety Data

• Hazardous Substances Data: 13165-35-0(Hazardous Substances Data)

Usage

General Description

7-Chloroquinazoline-2,4(1H,3H)-dione is a chemical compound that falls under the class of quinazolines, which are polycyclic aromatic compounds containing a benzene and a pyrimidine ring fused together. In specific, it is a dihydroxyquinazoline carrying a chloro substituent at position 7. However, not much information is available regarding its specific properties or applications, indicating that it is possibly an intermediary chemical compound used in various synthetic reactions for the production of more complex molecules. Furthermore, its safety properties, environmental effects, or health implications are not widely investigated or documented, underlining the need for more research in the field.

InChI:InChI=1/C8H5ClN2O2/c9-4-1-2-5-6(3-4)10-8(13)11-7(5)12/h1-3H,(H2,10,11,12,13)

Upstream product

• 57-13-6 urea 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 5900-58-3 2-amino-4-chloro-benzoic acid methyl ester 
• 7647-01-0 hydrogenchloride 
• 214288-97-8 4-chloro-2-ureido-benzoic acid 
• 38487-86-4 2-amino-4-chlorobenzonitrile 
• 68-12-2 N,N-dimethyl-formamide 
• 1352572-11-2 ethyl 7-chloro-4-oxo-4H-benzo[d][1,3]oxazine-2-carboxylate 
• 590-28-3 potassium cyanate 
• 917-61-3 sodium isocyanate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 41994-91-6 4-chloro-2-nitrobenzoic amide 
• 124-38-9 carbon dioxide 
• 85474-12-0 7-chloro-3-amino-2,4(1H,3H)-quinazolinedione 

Downstream Products

• 192570-39-1 1-(3,5-di-O-p-toluoyl-2-deoxy-α,β-D-erythro-pentofuranosyl)-7-chloro-quinazoline-2,4(3H)-dione 

Relevant articles and documents

Choline hydroxide promoted chemical fixation of CO2 to quinazoline-2,4(1H,3H)-diones in water

The efficient conversion of CO2 to high value-added chemicals in water with cheap and non-toxic catalysts is a very attractive topic in green chemistry. In this work, the transformation of CO2 and 2-aminobenzonitriles to quinazoline-2,4(1H,3H)-diones in water promoted by choline hydroxide has been studied. The effect of temperature, pressure, reaction time, and amount of catalyst on the reaction were investigated and the reaction conditions were optimized. It was demonstrated that choline hydroxide showed supernormal catalytic activity to promote this reaction as a biodegradable, environmentally friendly, green and cheap material showed supernormal catalytic activity to promote this reaction. Furthermore, the reaction mechanism was discussed.

A highly efficient way to capture CX2 (O, S) mildly in reusable ReILs at atmospheric pressure

The highly efficient transformation of CX2 (O, S) into valuable chemicals at atmospheric pressure is an attractive topic. A novel method of preparing quinazoline derivatives by capturing CX2 (O, S) in reusable, room-temperature, reversible ionic liquids (ReILs) with high yields (up to 98%) at 40 °C and atmospheric pressure was developed in this paper. The different reaction conditions were optimized and the products were easily separated from the ReILs which could be reused at least six times without considerable loss in yield. The plausible mechanism of capturing CX2 (O, S) in the ReILs was proposed and it provides a green, efficient protocol to capture CX2 (O, S) in ReILs to synthesize quinazoline derivatives. This journal is the Partner Organisations 2014.

Cyanuric Acid-Based Organocatalyst for Utilization of Carbon Dioxide at Atmospheric Pressure

A organocatalytic system based on economical and readily available cyanuric acid has been developed for the synthesis of 2-oxazolidinones and quinazoline-2,4(1H,3H)-diones from propargylamines and 2-aminobenzonitriles under atmospheric pressure carbon dioxide. Notably, a low concentration of carbon dioxide in air was directly converted into 2-oxazolidinone in excellent yields without an external base. Through mechanistic investigation by in situ FTIR spectroscopy, cyanuric acid was demonstrated to be an efficient catalyst for carbon dioxide fixation.

La-Mg mixed oxide as a highly basic water resistant catalyst for utilization of CO2 in the synthesis of quinazoline-2,4(1H,3H)-dione

The synthesis of quinazoline-2,4(1H,3H)-dione was done by direct utilization of CO2 in the cyclization of 2-aminobenzonitrile (2-ABN) using lanthanum magnesia mixed oxide (La-Mg MO) as a strong basic catalyst under mild reaction conditions in water. It gave a conversion of ～92% with 100% selectivity at 140 °C in 14 h. La-Mg MO was prepared by hydrothermal method using urea as homogeneous precipitating agent. The catalyst was characterized by different analytical techniques like BET, XRD, FT-IR, SEM, and TGA, and the basicity by CO2-TPD and acidity by NH3 TPD. Various reaction parameters were studied to predict the reaction mechanism and kinetics. The reaction follows the Langmuir-Hinshelwood-Hougen-Watson (LHHW) type kinetics model with an apparent activation energy of 23.3 kcal mol-1. The catalyst was recycled three times with an insignificant change in activity. The overall process is clean and green.

Is CO2 fixation promoted through the formation of DBU bicarbonate salt?

The bicyclic amidines, 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) and 1,5-diazabicyclo[4.3.0] non-5-ene (DBN), were used for the chemical fixation of carbon dioxide. The promotion for CO2 fixation is often reported through the formation of a thermally unstable DBU or DBN bicarbonate salt. To examine the effects of the DBU or DBN bicarbonate salt, reactions of 2-aminobenzonitrile with the DBU salt or DBN salt in dimethylformamide (DMF) were performed at 20°C for 24 h in argon or carbon dioxide (0.1 MPa). However, in all the cases, 1H-quinazoline-2,4-dione was not obtained completely. In contrast with room temperature reactions, 2-aminobenzonitriles and DBU bicarbonate salt in DMF reacted for 4 h under high temperature (80°C) and CO2 atmosphere (0.1 MPa) gave 1H-quinazoline-2,4-diones in good to excellent yields. At high-temperature conditions, DBU bicarbonate salt is decomposed to DBU and carbon dioxide. Also, the carbonylation of 2-aminobenzonitrile using DBU and carbon dioxide afforded 1H-quinazoline-2,4- dione in good yields under similar reaction conditions. These results suggest that the combination of DBU or DBN as a strong base and carbon dioxide is much more important than the in situ formation of DBU or DBN bicarbonate salt for the acceleration of CO2 fixation.

Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 catalyzed by N-heterocyclic carbene at atmospheric pressure

Under atmospheric pressure, quinazoline-2,4(1H,3H)-diones were obtained from the reaction of 2-aminobenzonitriles with carbon dioxide (0.1 MPa) with a catalytic amount of N-heterocyclic carbene in DMSO. It was found that various electron-donating and electron-withdrawing groups such as -OMe, -F, -Cl, -Br, -CH3, -CF3 and -CN were well tolerated to give the products in almost quantitative yields.

Condensation reaction of ethyl 4-oxo-4h-benzo[d][1,3]-oxazine-2- carboxylates with potassium cyanate: 2,4(1H,3H)-quinazolinediones synthesis

The condensation reaction of ethyl 4-oxo-4H-benzo[d][1,3]oxazine-2- carboxylates with acidic solution of potassium cyanate offers a novel and expedient route to the synthesis of 2,4(1H,3H)-quinazolinediones under mild reaction conditions..

Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles in water without any catalyst

We discovered that the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles could proceed efficiently in water without any catalyst and excellent yields were obtained, while the reaction did not occur in organic solvents

Amine functionalized MCM-41: An efficient heterogeneous recyclable catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from carbon dioxide and 2-aminobenzonitriles in water

A simple covalently linked amine functionalized MCM-41 compound was investigated using mesoporous catalytic protocols as a highly efficient, heterogeneous and recyclable catalyst for the synthesis of a wide variety of quinazoline-2,4(1H,3H)-dione derivatives from 2-aminobenzonitriles and carbon dioxide in aqueous reaction medium. This catalytic system represents a heterogeneous and environmentally benign protocol. The effect of various reaction parameters, such as the influences of solvent, temperature, CO 2 pressure, and time for the synthesis of quinazoline-2,4(1H,3H)- diones were studied. The developed protocol can be applied for the synthesis of the most important key intermediate 6,7-dimethoxyquinazoline-2,4(1H,3H)-dione and several biologically active derivatives such as Prazosin, Bunazosin and Doxazosin. Besides this, the developed catalyst could be reused for five consecutive recycles without any significant loss in its catalytic activity. The amine functionalized MCM-41 catalyst was characterized by various characterization techniques such as FT-IR, TGA/DTA, XRD, Scanning Electron Microscopy (SEM), Transmission Electron Microscopy (TEM), and solid state 29Si CP MAS NMR analysis. This journal is the Partner Organisations 2014.

Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 using ionic liquids as a dual solvent-catalyst at atmospheric pressure

The highly efficient transformation of CO2 into value-added chemicals is an interesting topic in green chemistry. In this work, we studied the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles in a series of ionic liquids (ILs). It was found that 1-butyl-3-methylimidazolium acetate ([Bmim]Ac), a simple and easily prepared IL, could act as both solvent and catalyst, the reactions could be carried out very efficiently at atmospheric pressure of CO2, and a high yield of the products was obtained. Further study indicated that the IL was also very efficient for converting other 2-aminobenzonitriles into their corresponding quinazoline-2,4(1H,3H)-diones in high yields at atmospheric pressure. Moreover, the separation of the products from the IL was very easy, and the IL could be reused at least five times without considerable loss in catalytic activity.

A protic ionic liquid catalyzes CO2 conversion at atmospheric pressure and room temperature: Synthesis of quinazoline-2,4(1H,3H)-diones

The chemical fixation of CO2 under mild reaction conditions is of significance from a sustainable chemistry viewpoint. Herein a CO 2-reactive protic ionic liquid (PIL), [HDBU+][TFE -], was designed by neutralization of the superbase 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with a weak proton donor trifluoroethanol (TFE). As a bifunctional catalyst for simultaneously activating CO2 and the substrate, this PIL displayed excellent performance in catalyzing the reactions of CO2 with 2-aminobenzonitriles at atmospheric pressure and room temperature, thus producing a series of quinazoline-2,4(1H,3H)-diones in excellent yields. No pressure: The reaction of CO2 with various 2-aminobenzonitriles was achieved at atmospheric pressure and room temperature by using the bifunctional protic ionic liquid [HDBU+][TFE-], thus producing the title compounds in excellent yields. The ionic liquid serves as both the catalyst and solvent, and activates both CO2 and the substrates simultaneously. DBU=1,8-diazabicyclo[5.4.0]undec-7-ene, TFE=trifluoroethanol.

Alcohol amine-catalyzed CO2conversion for the synthesis of quinazoline-2,4-(1H,3H)-dione in water

The conversion of CO2to high value-added chemicals in water using environment-friendly and cost-effective catalysts is a very significant topic. In this work, a green method for the conversion of CO2catalyzed by alcohol amines has been developed. Alcohol amines showed considerable activating ability to CO2in the cyclization with 2-aminobenzonitrile to quinazoline-2,4(1H,3H)-dione in water. Notably, when diethanolamine (DEA) was used as the catalyst, 94% yield of quinazoline-2,4-(1H,3H)-dione could be achieved. A plausible mechanism has been proposed based on the1H NMR, FT-IR analysis and DFT calculation. The excellent catalytic performance is attributed to the combined effect of both the secondary amine and hydroxyl groups on alcohol amines with the assistance of water in the formation of carbamate. Water plays a bi-functional role of solvent and co-catalyst in this catalytic process. Catalysts can be easily recovered and reused five times without significant loss of activity.

[TBDH][HFIP] ionic liquid catalyzed synthesis of quinazoline-2,4(1H,3H)-diones in the presence of ambient temperature and pressure

The utilization of carbon dioxide under mild reaction conditions is an important aspect of the sustainable chemistry point of view. Herein, we prepared three bifunctional protic ionic liquids having 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) as a cation and an alcohol anions were prepared by simple neutralization of the super base TBD with proton donor alcohols such as hexafluoroisopropanol (HFIP), TFE (2,2,2-Trifluoroethanol) and TFA (2,2,2-Trifluoroacetic acid). These PILs were used as catalysts for chemical fixation of carbon dioxide into quinazoline-2,4(1H,3H)-diones. [TBDH+][HFIP-] protic ionic liquid (PIL) shows very good result compare to other PILs. As a bifunctional ionic liquid, it simultaneously activates 2-aminobenzonitrile as well as CO2 and shows excellent performance for the conversion of 2-aminobenzonitrile to quinazoline-2,4(1H,3H)-diones in presence of CO2 balloon pressure at 35 °C temperature. Moreover, the [TBDH+][HFIP-] PIL can be recycled up to six recycle run.

Method for efficiently catalytically converting carbon dioxide into quinazoline diketone compound by using eutectic solvent under room temperature and atmospheric pressure conditions

The invention relates to a method for efficiently catalytically converting carbon dioxide into quinazoline diketone compounds by using a deep eutectic solvent under room temperature and atmospheric pressure conditions. According to the method, the deep eutectic solvent synthesized by adopting carbon dioxide and o-aminobenzonitrile with different substituent groups as raw materials, adopting ethylene glycol as a hydrogen bond donor, and adopting 1,5-diazabicyclo[4.3.0] non-5-ene (DBN) as a hydrogen bond acceptor, with the molar ratio of the hydrogen bond donor to the hydrogen bond receptor being 1:4, 1:1 and 4:1 is adopted as a catalyst, and the quinazoline diketone compound is synthesized at room temperature under atmospheric pressure for 1-24 h with the ratio of the substrate dosage to the catalyst dosage being 0.4: 3, 0.7: 3 and 1: 3. The invention provides the method for efficiently catalytically converting carbon dioxide into quinazoline diketone compounds by using the eutectic solvent under the conditions of room temperature and atmospheric pressure, and the method is simple and convenient, high in yield, low in cost, low in energy consumption, green and environment-friendly, avoids the use of a transition metal catalyst, and has very high practical application value.

DIACYLGLYCEROL KINASE MODULATING COMPOUNDS

The present disclosure provides diacylglycerol kinase modulating compounds, and pharmaceutical compositions thereof, for treating cancer, including solid tumors, and viral infections, such as HIV or hepatitis B virus infection. The compounds can be used alone or in combination with other agents.