28888-44-0

Usage

Uses

Used in Pharmaceutical Industry:
6,7-Dimethoxyquinazoline-2,4-dione is used as an intermediate in the preparation of Alfuzosin hydrochloride (A532000), which is an antihypertensive medication. 6,7-Dimethoxyquinazoline-2,4-dione contributes to the development of drugs that help regulate blood pressure and improve the overall cardiovascular health of patients.
Additionally, as an intermediate, 6,7-Dimethoxyquinazoline-2,4-dione may also be involved in the synthesis of other pharmaceutical compounds, further expanding its applications in the healthcare sector.

InChI:InChI=1/C10H10N2O4/c1-15-7-3-5-6(4-8(7)16-2)11-10(14)12-9(5)13/h3-4H,1-2H3,(H2,11,12,13,14)

Upstream product

• 590-28-3 potassium cyanate 
• 5653-40-7 2-Amino-4,5-dimethoxybenzoic acid 
• 124-38-9 carbon dioxide 
• 26961-27-3 2-amino-4,5-dimethoxybenzonitrile 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 917-61-3 sodium isocyanate 
• 57-13-6 urea 
• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 68-12-2 N,N-dimethyl-formamide 
• 1352572-08-7 ethyl 6,7-dimethoxy-4-oxo-4H-benzo[d][1,3]oxazine-2-carboxylate 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 859912-32-6 4,5-dimethoxy-2-ureido-benzoic acid 

Downstream Products

• 27631-29-4 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 
• 938515-42-5 4-(3-carboxyanilino)-2-chloro-6,7-dimethoxyquinazo line 
• 100448-62-2 4-(6,7-Dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-ylamino)-benzoic acid 

Relevant academic research and scientific papers

Synthesis of 2,4-dihydroxyquinazolines using carbon dioxide in the presence of DBU under mild conditions

Chemical fixation of carbon dioxide was performed under mild conditions. Carbon dioxide (1 atm) easily reacted with 2-aminobenzonitriles at 20°C, assisted by DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) to give 2,4- dihydroxyquinazolines in excellent yields.

[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.

Proton type ionic liquid [HDBN] [2-PyOH] and preparation and application thereof

The invention discloses proton type ionic liquid [HDBN] [2-PyOH] and preparation and application thereof, and belongs to the technical field of catalysts. The preparation method comprises the steps that 1, 5-diazabicyclo [4.3. 0] nonyl-5-ene reacts with 2-hydroxypyridine to prepare protonic ionic liquid [HDBN] [2-PyOH]; and as a catalyst, the ionic liquid can catalyze CO2 and o-aminobenzonitrile compounds to efficiently react under mild conditions to obtain a series of quinazoline-2, 4 (1H, 3H)-diketone compounds. The proton type ionic liquid catalyst has the advantages of simple synthesis process, excellent catalytic performance, good substrate expansion capability, easy product separation and the like, and has a good industrial application prospect.

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.

Synthesis method of 2, 4-(1H, 3H)-quinazolinedione and derivatives thereof

The invention discloses a synthesis method of 2, 4-(1H, 3H)-quinazolinedione and derivatives thereof. CO2 and aminobenzonitrile compounds are used as raw materials, and the 2, 4-(1H, 3H)-quinazolinedione and the derivatives thereof are obtained through a reaction by adopting a catalyst as shown in the formula I provided by the invention. Reagents used in the method are cheap and easy to obtain, the product can be synthesized through a one-step method, harsh conditions of high pressure and high temperature are not needed, no metal is left in the whole reaction system, and the used catalyst canbe recycled.

Efficient transformation of CO2 into quinazoline-2,4(1: H,3 H)-diones at room temperature catalyzed by a ZnI2/NEt3 system

The readily available ZnI2/NEt3 system was used firstly to catalyze the transformation of CO2 and 2-aminobenzonitriles into quinazoline-2,4(1H,3H)-diones at room temperature and low CO2 pressure in high yields. Further experiments indicated that this ZnI2/NEt3 system has excellent effects on activating both amino and cyano groups.

CO2 involved synthesis of quinazoline-2,4(1 H,3 H)-diones in water using melamine as a thermoregulated catalyst

In this study, pharmaceutically relevant quinazoline-2,4(1H,3H)-diones were synthesized eco-efficiently by cycloaddition of CO2 and 2-aminobenzonitrile in water, catalyzed by melamine as a thermoregulated catalyst. Quinazoline-2,4(1H,3H)-dione was produced selectively with 92% yield at 120 °C, 4.2 MPa, and automatically separated from the hot catalytic aqueous solution, which was reused directly for several runs until its activity decreased in an obvious manner. Then, the catalyst melamine was recrystallized from the spent aqueous solution via simple cooling and reused for another several catalytic runs. The efficient valorization of CO2 and the straightforward stepwise recovery of the products and catalyst were important to save energy and minimize process waste for the practical industrial production.

Facile and efficient synthesis of quinazoline-2,4(1H,3H)-diones through sequential hydrogenation condensation

The heterocyclizations from various methyl (2-nitrobenzoyl)carbamates to substituted quinazoline-2,4(1H,3H)-diones under hydrogenation conditions were investigated in this study. In the presence of p-toluenesulfonic acid monohydrate in methanol, various q

Efficient synthesis of 2-oxazolidinones and quinazoline-2,4(1H,3H)-diones from CO2 catalyzed by tetrabutylammonium fluoride

By employing tetrabutylammonium fluoride (TBAF) as a catalyst, the various carboxylative cyclizations of the propargylic amines having internal alkynes with CO2 proceeded to afford the corresponding 2-oxazolidinones. In this case, it was also found that the generated 2-oxazolidinones were tautomerized into the corresponding 2-oxazolones due to the basicity of TBAF. In addition, we performed the synthesis of quinazoline-2,4(1H,3H)-dione from 2-aminobenzonitrile and CO2 by using TBAF as a catalyst.

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.