13165-35-0

Usage

Uses

Used in Pharmaceutical Industry:
7-Chloroquinazoline-2,4(1H,3H)-dione is used as an intermediate chemical compound for the synthesis of more complex molecules, potentially leading to the development of new pharmaceuticals. Its role in this industry is to facilitate the creation of novel drug candidates that could address various medical conditions.
Used in Chemical Research:
In the field of chemical research, 7-chloroquinazoline-2,4(1H,3H)-dione serves as a subject for investigation, allowing scientists to explore its reactivity, stability, and potential applications in the synthesis of other compounds. This research could contribute to the advancement of chemical knowledge and the discovery of new synthetic pathways.
Note: Due to the limited information available on 7-chloroquinazoline-2,4(1H,3H)-dione, the applications listed above are speculative and based on the general understanding of similar compounds. Further research and investigation are necessary to confirm its specific uses and potential benefits in various industries.

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 
• 7647-01-0 hydrogenchloride 
• 214288-97-8 4-chloro-2-ureido-benzoic acid 
• 124-38-9 carbon dioxide 
• 38487-86-4 2-amino-4-chlorobenzonitrile 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 41994-91-6 4-chloro-2-nitrobenzoic amide 
• 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 
• 85474-12-0 7-chloro-3-amino-2,4(1H,3H)-quinazolinedione 
• 5900-58-3 2-amino-4-chloro-benzoic acid methyl ester 

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 
• 192570-59-5 1-[2-deoxy-5-(4,4'-dimethoxytrityl)-α-D-erythro-pentofuranosyl]-7-chloro-quinazoline-2,4(3H)-dione 
• 192570-54-0 1-[2-deoxy-5-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-7-chloro-quinazoline-2,4(3H)-dione 
• 111218-91-8 2,7-dichloro-quinazolin-4-ylamine 
• 111218-71-4 [4-(4-Amino-7-chloro-quinazolin-2-yl)-piperazin-1-yl]-furan-2-yl-methanone 
• 111218-75-8 [4-(4-Amino-7-chloro-6,8-dinitro-quinazolin-2-yl)-piperazin-1-yl]-furan-2-yl-methanone; hydrochloride 
• 112733-28-5 ethyl 2-[3-(4-bromo-2-fluorobenzyl)-7-chloro-1,2,3,4-tetrahydro-2,4-dioxoquinazoline-1-yl)acetate 
• 112733-06-9 zenarestat 
• 112733-45-6 ethyl 2-(7-chloro-1,2,3,4-tetrahydro-2,4-dioxoquinazoline-1-yl)acetate 

Relevant academic research and scientific papers

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.

Carbon Dioxide Mediated Novel Synthesis of Quinazoline-2,4(1H,3H)-dione in Water

A novel, efficient, and scalable CO2 mediated synthesis of quinazoline-2,4(1H,3H)-dione was developed by a simple cyclization of 2-aminobenzonitrile with DMF in water as the solvent. This is the first report of its kind. DMF was used as the necessary carbon source in the synthesis of quinazoline-2,4(1H,3H)-dione. This synthetic protocol is very efficient; it gives >99% conversion with excellent selectivity. The product was isolated by filtration because of the highly insoluble nature of quinazoline-2,4(1H,3H)-dione in water. The co-product, dimethyl amine, also has industrial importance, and the CO2 that is used can be recycled. This protocol has wide-spread applications in the syntheses of benzimidazole and benzothiazole.

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.

Tetra-butylphosphonium arginine-based ionic liquid-promoted cyclization of 2-aminobenzonitrile with carbon dioxide

An easily prepared amino acid ionic liquid (AAIL) i.e. [TBP][Arg] comprising a tetra-butylphosphonium cation and an arginine anion was found to be an efficient and recyclable catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from 2-aminobenzonitriles and CO2 under solvent-free conditions. As a result, various 2-aminobenzonitriles bearing electron-withdrawing or electron-donating substituents worked well to afford quinazoline-2,4(1H,3H)-diones in excellent yields. Notably, this type of AAIL showed good stability, and could be easily recovered and reused five times without significant loss of its catalytic activity. This process represents an alternative approach for greener chemical fixation of CO2 to afford valuable compounds. This journal is

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.

Solvent-free synthesis of quinazoline-2,4(1H,3H)-diones using carbon dioxide and a catalytic amount of DBU

An ideal reaction system, which is aimed at sustainable chemistry, was developed. Under solvent-free conditions, quinazoline-2,4(1H,3H)-diones were obtained in good to excellent yields from 2-aminobenzonitriles with only carbon dioxide (1 bar) and a catalytic amount of base (DBU or DBN). For example, 6,7-dimethoxyquinazoline-2,4(1H,3H)-dione, which is a key intermediate of several drugs (Prazosin, Bunazosin, and Doxazosin) was synthesized successfully in 97% yield [DBU (0.2 equiv), CO2 (1 bar), 120°C]. Georg Thieme Verlag Stuttgart.

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.

Highly efficient synthesis of 1H-quinazoline-2,4-diones using carbon dioxide in the presence of catalytic amount of DBU

The first example of chemical fixation of carbon dioxide in the presence of catalytic amount of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or DBN (1,5-diazabicyclo[4.3.0]non-5-ene) was developed. Carbon dioxide easily reacted with 2-aminobenzonitriles under

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.

Basic Salt-Lake Brine: An Efficient Catalyst for the Transformation of CO2 into Quinazoline-2,4(1 H,3 H)-diones

The efficient transformation of CO2 into value-added chemicals with green, abundant, and cheap catalysts is an interesting and challenging topic in both green and sustainable chemistry. In this study, a series of salt-lake brines were used for the first time to catalyze the reaction of CO2 and a broad range of 2-aminobenzonitriles to form the corresponding quinazoline-2,4(1 H,3 H)-diones. It was found that the abundant, available, and inexpensive Zhabuye basic salt-lake brine could efficiently promote the reaction of 2-aminobenzonitriles under low pressure of CO2. Very high yields of value-added products were obtained. Further studies indicated that the basic carbonate and borate ions in the brine play key roles in accelerating the reactions.