13182-64-4

Usage

Uses

Used in Pharmaceutical Industry:
2-ISOPROPYL-QUINAZOLIN-4-OL is used as a potential therapeutic agent for the treatment of neurological disorders due to its neuroprotective effects in certain models of brain injury.
Used in Anticancer Applications:
2-ISOPROPYL-QUINAZOLIN-4-OL is used as an anti-cancer agent, with studies showing its cytotoxic effects on cancer cells, making it a promising candidate for the development of new therapeutic agents for cancer treatment.
Used in Antioxidant and Anti-inflammatory Applications:
2-ISOPROPYL-QUINAZOLIN-4-OL is used as an antioxidant and anti-inflammatory agent, leveraging its properties to potentially treat conditions where oxidative stress and inflammation play a significant role in disease progression.

InChI:InChI=1/C11H12N2O/c1-7(2)10-12-9-6-4-3-5-8(9)11(14)13-10/h3-7H,1-2H3,(H,12,13,14)

Upstream product

• 6141-06-6 2-isopropylquinazoline 
• 97-72-3 2-Methylpropionic anhydride 
• 118-92-3 anthranilic acid 
• 75-05-8 acetonitrile 
• 107-12-0 propiononitrile 
• 1885-29-6 anthranilic acid nitrile 
• 563-83-7 ISOPROPYLAMIDE 
• 4406-41-1 N-phenylisobutyramide 
• 51-79-6 urethane 
• 62961-62-0 (Z)-3-hydroxy-1,3-diphenyl-2-propen-1-one 
• 160422-27-5 3-(acetoxyamino)-2-isopropylquinazolin-4-one 
• 1704-14-9 4-hydroxy-4-phenylbut-3-en-2-one 
• 67-56-1 methanol 
• 160422-28-6 1-(2-Isopropyl-4-oxo-4H-quinazolin-3-ylamino)-2-oxo-cyclopentanecarboxylic acid ethyl ester 

Downstream Products

• 38154-42-6 4-chloro-2-isopropyl-quinazoline 
• 281661-73-2 2-(1-methylethyl)-4-phenylquinazoline 
• 1429045-90-8 C₂₅H₂₂N₆S 
• 1429046-07-0 C₂₅H₂₂N₂O₂S 
• 1429046-05-8 C₂₅H₂₂N₂O₂S 
• 1429046-04-7 C₂₅H₂₂N₂O₂S 
• 1429046-03-6 C₂₆H₂₄N₂O₂S 
• 1429046-02-5 C₂₆H₂₄N₂O₂S 
• 1429046-01-4 C₂₆H₂₄N₂O₂S 
• 1429045-97-5 C₂₅H₂₁N₃S 

Relevant academic research and scientific papers

Photoelectrochemical C?H Alkylation of Heteroarenes with Organotrifluoroborates

A photoelectrochemical method for the C?H alkylation of heteroarenes with organotrifluoroborates has been developed. The merger of electrocatalysis and photoredox catalysis provides a chemical oxidant-free approach for the generation and functionalization

Reaction of 3-(Acetoxyamino)quinazolin-4(3H)-ones with Enolic β-Diketones: the N-N Bond as a Chiral Axis in N-(3,4-dihydro-4-oxoquinazolin-3-yl)-N-acyl-α-aminoketones; Reductive and Base-catalysed Cleavage of the N-N Bond in N-Acetyl-N-(3,4-dihydro-4-oxoquinazolin-3-yl)-α-amino Aci...

Following the method of Foucaud and coworkers, reaction of pentane-2,4-dione with 3-(acetoxyamino)quinazolin-4-one 8 gave the keto amide 9 (15percent). 3-Methylpentane-2,4-dione reacts with compound 8 to give a relatively stable enol 11 (66percent) which can be isolated in a crystalline form.Rotation around the N-N bonds in both compounds 9 and 11 is believed to be slow on the real time-scale and hence the N-N bonds can be considered as a chiral axes.As a result, protonation of the enol double bond in compound 11 and the creation of an additional chiral centre, gives rise to the separable keto amides 14 and 15; this protonation can be accomplished completely diastereoselectively.Lead tetraacetate acetoxylation of compound 11 to give compound 11 to give compound 19 is also completely diastereoselective.Brief heating of the enol effects the elimination of the quinazolinone and the formation of the N-acetylimine 16 via an 8-membered transition state.Base-catalysed elimination of the quinazolinone ring from compound 22 is surprisingly easy: reductive cleavage of this N-N bond in compound 22 is facile by comparison with the 3-(alkylamino)quinazolin-4-ones.

Carbon-hydrogen bond insertion reactions of 3-acetoxyaminoquinazolin-4(3H)-ones with cyclic dienes: Stereochemistry and mechanism

Reaction of 2-substituted-3-acetoxyaminoquinazolin-4(3H)-ones (QNHOAc) with cyclohexa-1,3-diene or cyclohexa-1,4-diene (2equiv.) gives, besides the expected aziridination products, stable dihydroaromatic by-products formally arising by insertion of [QN?:] into one of the doubly allylic C-H bonds. An analogous insertion into the methylene C-H bonds of 9,10-dihydroanthracene or xanthene (1.5-2 equiv.) occurs. Using 3-acetoxyamino-2-[(S)-2,2-dimethyl-1-hydroxypropyl]quinazolin-4(3H)-one 2 (Q1NHOAc) in the presence of titanium(IV) t-butoxide, insertion into cyclohexa-1,3-diene takes place completely diastereoselectively and the configuration at the cyclohexadienyl ring carbon has been correlated with that at the 6-position of the major aziridine diastereoisomer co-produced in the reaction. A mechanism involving concerted insertion into the C-H bond of the diene by QNHOAc is proposed with endo-overlap of both double bonds of the diene with the Q group in the transition state.

Photoredox Catalysis for Silyl-Mediated C–H Alkylation of Heterocycles with Non-Activated Alkyl Bromides

The development of a Minisci reaction of electron-deficient heteroarenes with non-activated alkyl bromides under visible-light photoredox catalysis is disclosed. Optimization of the reaction led to identification of mild, general, and practical reaction c

Catalyst-free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives

A general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.

Visible-light- And bromide-mediated photoredox Minisci alkylation of N-heteroarenes with ester acetates

A visible-light-induced photoredox Minisci alkylation reaction of N-heteroarenes with ethyl acetate has been reported. The low-toxic ethyl acetate was used for the first time as an alkylation reagent. Hence, 4-quinazolinones, quinolines and pyridines reacted smoothly in the current reaction system. Mechanistic studies indicate that LiBr plays a key role to dramatically improve the efficiency of the reaction by the mediation of hydrogen atom transfer. This journal is

Visible-light-mediated minisci C-H alkylation of heteroarenes with 4-alkyl-1,4-dihydropyridines using O2as an oxidant

Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation reactions of N-heteroarenes with 4-alkyl-1,4-dihydropyridines at room temperature with molecular oxygen as an oxidant. The protocol permits efficient functionalization of various N-heteroarenes with a broad range of cyclic and acyclic primary, secondary, and tertiary alkyl groups and is scalable to the gram level. This mild protocol uses an inexpensive, green oxidant and is suitable for late-stage C-H alkylation of complex nitrogen-containing molecules. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.

Imidazolium chloride as an additive for synthesis of 4(3H)-quinazolinones using anthranilamides and DMF derivatives

Imidazolium chloride as an environmentally benign additive efficiently facilitates construction of 4(3H)-quinazolinones using anthranilamides and DMF derivatives. A series of 4(3H)-quinazolinones were prepared in moderate to excellent yields without conventional oxidants, metal catalysts and corrosive acids or other additives.

A in ammonia water condition of microwave halo benzoic acid synthesis method of the quinazoline compounds

The invention discloses a in ammonia water condition of microwave halo benzoic acid synthetic quinazoline compounds of the method, the use of palladium chloride to serve as the catalyst, in ammonia water under the microwave heating condition, neighbouring halogen benzoic acid generated by the reaction with the isocyanate of the quinazoline compounds of the method, the invention an environment-friendly, the operation is simple, cheap and safe, efficient process for producing quinazoline compounds of the method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection.

A in the aqueous phase under microwave conditions using halogenated benzamide fast synthesis of quinazoline compounds of the method

The invention discloses a in the aqueous phase under microwave conditions using halogenated benzamide fast synthesis of quinazoline compounds of the method, the use of palladium chloride to serve as the catalyst, in water under microwave heating conditions, neighbouring halogen benzamide with an isocyanate reaction to produce the quinazoline compounds of the method, the invention an environment-friendly, the operation is simple, cheap and safe, efficient process for producing quinazoline compounds of the method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection.