1207-75-6

Usage

Uses

Used in Pharmaceutical Synthesis:
3-(2-Hydroxyethyl)-2,4-(1H,3H)-quinazoline-dione is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be a valuable building block in the creation of new drug molecules, contributing to the development of novel therapeutic agents.
Used in Organic Chemistry Research:
In the field of organic chemistry, 3-(2-Hydroxyethyl)-2,4-(1H,3H)-quinazoline-dione is used as a model compound for studying the properties and reactions of quinazoline derivatives. This helps researchers understand the reactivity and potential applications of similar compounds in the synthesis of complex organic molecules.
Used in Drug Discovery:
3-(2-Hydroxyethyl)-2,4-(1H,3H)-quinazoline-dione is also used in drug discovery processes. Its potential biological and pharmacological activities make it a candidate for further investigation into its possible use as a therapeutic agent or as a component in the development of new drugs.
Used in the Chemical Industry:
3-(2-Hydroxyethyl)-2,4-(1H,3H)-quinazoline-dione is utilized in the chemical industry for the production of various organic compounds. Its versatility in chemical reactions and its ability to form a range of derivatives make it a valuable asset in the synthesis of specialty chemicals and materials.

InChI:InChI=1/C10H10N2O3/c13-6-5-12-9(14)7-3-1-2-4-8(7)11-10(12)15/h1-4,13H,5-6H2,(H,11,15)

Upstream product

• 57212-70-1 N-(mesyloxy)phthalimide 
• 141-43-5 ethanolamine 
• 77189-70-9 2-<3-(2-cloroethyl)ureido>benzonitrile 
• 77093-93-7 2-(2-chloroethylamino)-4H-<3,1>benzoxazin-4-one 
• 1885-29-6 anthranilic acid nitrile 
• 108890-73-9 ethyl 2-((ethoxycarbonyl)amino)benzoate 
• 87-25-2 2-ethoxycarbonylaniline 
• 83846-67-7 methyl 2-((ethoxycarbonyl)amino)benzoate 
• 91-56-5 indole-2,3-dione 
• 7143-42-2 methyl 2-((methoxycarbonyl)amino)benzoate 
• 82603-69-8 methyl 1,4-dihydro-2,4-dioxoquinazoline-3(2H)-acetate 
• 134-20-3 2-carbomethoxyaniline 
• 118-92-3 anthranilic acid 
• 77093-92-6 methyl 2-<3-(2-chloroethyl)ureido>benzoate 

Downstream Products

• 1029791-08-9 ethyl 2-[2,4-dioxo-1,2-dihydroquinazoline-3(4H)-yl]benzoate 
• 5081-87-8 3-(2-chloroethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline 
• 83846-83-7 ketanserin tartrate 
• 74050-98-9 ketanserine 
• 52727-44-3 2,3-dihydro-5H-oxazolo<2,3-b>quinazolin-5-one 

Relevant academic research and scientific papers

Synthesis, crystal structure, spectral and DFT studies of potent isatin derived metal complexes

The isatin-core in compounds offers exciting perspectives in medicinal and pharmacological research. The present study reports the successful development of new isatin-core transition metal based anti-bacterial complexes via conventional refluxing method.

Synthesis of quinazolindionyl amino acid and hydrazone derivatives as possible antitumour agents

A series of 1-ethyl-2,4-dioxo-(1H,3H)-quinazolin-3-yl amino acid and hydrazone derivatives were synthesized and tested for their antitumor activity. The alcohol and acid derivatives of quinazolindione were conjugated with the amino acid derivatives at N-3 site via ester or amide bonds by carbodiimide and azide methods. The carbodiimide-mediated amide and esterification steps were performed in the presence of HOBt or DMAP respectively otherwise the side-products N-acyl urea derivatives are formed, instead of the desired derivatives. Nine compounds exhibited encouraging antitumor activity against human liver carcinoma cell line (HepG2).

Ketoserin intermediate and preparation method of ketoserin

The invention discloses a preparation method of a ketoserin intermediate 2, 3-dihydro-5H-oxazolo[2, 3-B]quinazoline-5-ketone and a preparation method of ketoserin, and the reaction equation of the preparation method of the ketoserin intermediate 2, 3-dihydro-5H-oxazolo[2, 3-B]quinazoline-5-ketone is shown in the specification: in the reaction, sodium carbonate and acetonitrile are used, no catalyst is added, inorganic salt is removed through hot filtration after the reaction, filtrate is evaporated to dryness, acetonitrile is recycled, and an intermediate 04, namely the ketoserin intermediate2, 3-dihydro-5H-oxazolo[2, 3-B]quinazoline-5-ketone, is obtained. The method is simple and convenient to operate, lower in cost, better in product character and more beneficial to synthesis of a finalproduct.

Reinvestigation of the synthesis of ketanserin (5) and its hydrochloride salt (5.HCl) via 3-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione (2) or dihydro-5H-oxazole(2,3-b)quinazolin-5-one (1)

The synthesis of ketanserin (5) and its hydrochloride salt (5.HCl) using respectively equimolar amounts of 3-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione (2) with 4-(parafluorobenzoyl)piperidine (3) and dihydro-5H-oxazole(2,3-b) quinazolin-5-one (1) with hydrochloride salt of 4-(parafluorobenzoyl)piperidine (3.HCl) is reinvestigated. The one-pot reaction of ethyl-2-aminobenzoate with ethyl chloroformate and ethanol amine has afforded 3-(2-chloroethyl)-2,4-(1H,3H) -quinazolinedione (2) (86%) that was then refluxed with 4-(parafluorobenzoyl) piperidine (3) in ethyl methyl ketone in the presence of sodium carbonate to obtain free base of ketanserin (87%). In another attempt, a very pure hydrochloride salt of ketanserin (5.HCl) was synthesized using equimolar amounts of dihydro-5H-oxazole(2,3-b)quinazolin-5-one (1) and hydrochloride salt of 4-(parafluorobenzoyl)piperidine (3.HCl) by a solvent-less fusion method. Thus, under optimized conditions, 180°C and a reaction time of 30 min, the powder mixture was transformed into glassy crystals that were initially readily soluble in chloroform but were transformed afterwards over time (2 h) to white precipitates (5.HCl) suspended in chloroform with a yield of 72%.

4-Hydroxy-2-quinolones 173. 1-R-3-(2-diethylamino- ethyl)-1H-quinazoline- 2,4-dione hydrochlorides as potential local anesthetic agents

Different variants of the preparation and procedures in the synthesis of a series of 1-R-3-(2-dialkyl-aminoethyl)-1H-quinazoline-2,4-dione hydrochlorides having a structural similarity to the 4-hydroxy-2-quinolinone anesthetic chinoxicaine are discussed. A comparative analysis of the biological properties of the synthesized compounds and the known local anesthetics chinoxicaine and lidocaine is reported.

N-substituted alpha-arylazacycloalkylmethanamines and their use as cardiovascular agents

Novel compounds of the formula below wherein W is azetidine, pyrrolidine or piperidine, Q is a straight chain hydrocarbon radical of 1-4 carbons and may contain a double bond, and STR1 Ar is phenyl, pyridinyl or pyrimidinyl, a process for their preparation, and novel intermediates are disclosed. The novel compounds and the pharmaceutical compositions of this invention are useful in the treatment of hypertension, arrhythmias and angina.

Reactions of o-Aminonitriles with Isocyanates. 1. A Two-Step Synthesis of 2,6-Dihydroimidazoquinazolin-5-(3H)one

The reaction of anthranilonitrile with 2-chloroethyl isocyanate yields 2-benzonitrile (6) which, upon heating, or treatment with base, undergoes a double cyclization to form 2,6-dihydroimidazoquinazolin-5-(3H)one (8) in excellent yield.When heated with hydrochloric acid, 6 is converted initially into 2-(2-chloroethylamino)-4H-benzoxazin-4-one (18) and further into 3-(2-chloroethyl)-2,4-(1H,3H)quinazolinedione (15).The acid-catalyzed reaction of 2,3-dihydro-5H-oxazoloquinazolin-5-one (14) with nucleophilic reagents yields 3-substituted 2,4-(1H,3H)quinazolinediones.