16499-58-4

Usage

Uses

Used in Medicinal Chemistry:
7-(TRIFLUOROMETHYL)QUINAZOLIN-4(3H)-ONE is used as a key intermediate in the synthesis of pharmaceuticals for its potential to exhibit biological activities that can be harnessed for therapeutic purposes.
Used in Drug Development:
As a compound with a quinazolin-4(3H)-one core, 7-(TRIFLUOROMETHYL)QUINAZOLIN-4(3H)-ONE is utilized in drug development to create new medications, potentially targeting a range of diseases and conditions.
Used in Agrochemicals Synthesis:
7-(TRIFLUOROMETHYL)QUINAZOLIN-4(3H)-ONE is used as a starting material in the synthesis of agrochemicals, where its unique structure and properties can contribute to the development of effective crop protection agents.
Used in Research and Development:
7-(TRIFLUOROMETHYL)QUINAZOLIN-4(3H)-ONE is employed in research and development settings to explore its chemical properties, reactivity, and potential applications in various industries, including but not limited to pharmaceuticals and agrochemicals.
Used in Chemical Property Studies:
7-(TRIFLUOROMETHYL)QUINAZOLIN-4(3H)-ONE is used in studies focused on understanding the effects of the trifluoromethyl group on the chemical and physical properties of heterocyclic compounds, which can lead to innovations in material science and chemical engineering.

Upstream product

• 64-18-6 formic acid 
• 778-94-9 2-nitro-4-trifluoromethyl-benzonitrile 
• 67-56-1 methanol 
• 713-41-7 2-amino-4-(trifluoromethyl)benzamide 
• 402-13-1 2-amino-4-trifluoromethylbenzoic acid 
• 77287-34-4 formamide 

Downstream Products

• 374556-29-3 N-[3-(1,2-dimethyl-1H-imidazol-5-yl)phenyl]-7-(trifluoromethyl)-4-quinazolinamine 
• 374556-30-6 N-[3-(4,5-dimethyl-1H-imidazol-1-yl)phenyl]-7-(trifluoromethyl)-4-quinazolinamine 
• 16499-65-3 4-chloro-7-trifluoromethyl-quinazoline 
• 129190-40-5 2,6-bis(4'-benzylpiperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-32-5 2,6-bis(dipentylaminomethyl)-4-(7'-trifluoromethylquinazolin-4'-ylamino)phenol 
• 129190-38-1 2,6-bis(3',5'-dimethylpiperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-36-9 2,6-bis(3'-methylpiperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-37-0 2,6-bis(4'-methylpiperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-35-8 2,6-bis(piperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-30-3 2,6-bis(dipropylaminomethyl)-4-(7'-trifluoromethylquinazolin-4'-ylamino)phenol 
• 129210-19-1 2,6-bis(pyrrolidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-34-7 2,6-bis(N-butyl-N-methylaminomethyl)-4-(7'-trifluoromethylquinazolin-4'-ylamino)phenol 
• 129190-29-0 2,6-bis(diethylaminomethyl)-4-(7'-trifluoromethylquinazolin-4'-ylamino)phenol 
• 129190-28-9 2,6-bis(dimethylaminomethyl)-4-(7'-trifluoromethylquinazolin-4'-ylamino)phenol 

Relevant academic research and scientific papers

Self-catalyzed phototandem perfluoroalkylation/cyclization of unactivated alkenes: Synthesis of perfluoroalkyl-substituted quinazolinones

A novel visible-light-induced radical tandem trifluoromethylation/cyclization of unactivated alkenes with sodium perfluoroalkanesulfinates (Rf = CF3, C3F7, C4F9, C6F13, C8F17) under air atmosphere has been developed. A range of quinazolinones containing unactivated alkene moiety and sodium perfluoroalkanesulfinates were compatible with this transformation, leading to a variety of perfluoroalkyl-substituted quinazoline alkaloids. Remarkably, the experiment can be carried out without any metal catalyst, strong oxidant, or external photosensitizer.

Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives

A novel and green strategy for the synthesis of acylated quinazolinone derivativesviaphoto-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without any external photocatalyst, additive or oxidant, and could be easily scaled-up in flow conditions with sunlight irradiation.

Photo-triggered self-catalyzed fluoroalkylation/cyclization of unactivated alkenes: Synthesis of quinazolinones containing the CF2R group

A novel photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed. This transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note is that this is the first example describing the Csp3-Br bond homolysis of alkyl bromides via a substrate (quinazolinones) induced energy transfer process. Additionally, the mild conditions, tolerance to a wide range of functional groups and operational simplicity make this protocol practical for the synthesis of fluorine-containing ring-fused quinazolinones. This journal is

Visible-Light-Induced Radical Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Quinazolinones

A mild and efficient visible-light-induced radical difluoromethylation/cyclization of unactivated alkenes toward the synthesis of substituted quinazolinones with easily accessible difluoromethyltriphenylphosphonium bromide has been developed. The transformation has the advantages of wide functional group compatibility, a broad substrate scope, and operational simplicity. The benign protocol offers a facile access to pharmaceutically valuable difluoromethylated polycyclic quinazolinones.

HARMFUL ARTHROPOD CONTROL METHOD USING HETEROCYCLIC COMPOUND

PROBLEM TO BE SOLVED: To provide a method for controlling a harmful arthropod. SOLUTION: The compound shown by the formula (I) [in the formula, Q represents the group, etc. represented by the formula Q1, Z represents an oxygen atom, etc., A1 re

Method of synthesizing quinazolinone derivative by using methanol as raw material

The invention discloses a method of synthesizing a quinazolinone derivative by using methanol as a raw material. The method comprises adding an anthranilamide derivative II, methanol III and an iridium metal complex in a reaction container; performing a reaction on the reaction mixture in a microwave reactor or under magnetic stirring at a temperature of 130 +/- 10 DEG C for 2 hours or more; performing cooling to a room temperature; removing a solvent in a spin drying manner; and performing column separation to obtain a target compound. The method provided by the invention adopts nontoxic and renewable methanol as a raw material, and the by-products in the reaction are hydrogen gas and water, thus the method does not pollute the environment and meet the requirements of green chemistry, so that the method has a wide development prospect.

Acceptorless Dehydrogenative Coupling of o-Aminobenzamides with the Activation of Methanol as a C1 Source for the Construction of Quinazolinones

A strategy for the synthesis of quinazolinones via acceptorless coupling of o-aminobenzamides with methanol has been accomplished in the presence of the metal-ligand bifunctional catalyst [Cp?Ir(2,2′-bpyO)(H2O)]. Notably, this research exhibited the potential of transition-metal-catalyzed activation of methanol as a C1 source for the construction of heterocycles.

Synthesis and SAR optimization of quinazolin-4(3H)-ones as poly(ADP-ribose)polymerase-1 inhibitors

We have demonstrated that quinazolin-4(3H)-one, a nicotinamide (NI) mimic with PARP-1 inhibitory activity in the high micromolar range (IC50 = 5.75 μM) could be transformed into highly active derivatives with only marginal increase in molecular weight. Convenient one to two synthetic steps allowed us to explore extensive SAR at the 2-, and 5- through 8-positions of the quinazolin-4(3H)-one scaffold. Substitutions at the 2- and 8-positions were found to be most favorable for improved PARP-1 inhibition. The amino group at 8-position resulted in compound 22 with an IC50 value of 0.76 μM. Combination of the 8-amino substituent with an additional methyl substituent at the 2-position provided the most potent compound 31 [8-amino-2-methylquinazolin- 4(3H)-one, IC50 = 0.4 μM] in the present study. Compound 31 inhibited the proliferation of Brca1-deficient cells with an IC50 value of 49.0 μM and displayed >10-fold selectivity over wild type counterparts. Binding models of these derivatives within the active site of PARP-1 have further supported the SAR data and will be useful for future lead optimization efforts.

One-pot conversion of 2-nitrobenzonitriles to quinazolin-4(3H)-ones and synthesis of gefitinib and erlotinib hydrochloride

A simple and efficient one-pot conversion of 2-nitrobenzonitriles to quinazolin-4(3H)-ones involving reduction, formylation, hydrolysis and cyclization is reported. These quinazolinones have been used for making in economical way the anticancer drug molecules gefitinib (Iressa) and erlotinib HCl (Tarceva).

Potential Antimalarials. IX Di-Mannich Bases of 4-(7'-Trifluoromethylquinazolin-4'-ylamino)phenol and 4-(7'-Trifluoromethylquinolin-4'-ylamino)phenol

Syntheses are reported for a series of di-Mannich bases of 4-(7'-trifluoromethylquinazolin-4'-ylamino)phenol derived from 4-chloro-7-trifluoromethylquinazoline with the di-Mannich bases of 4-aminophenol.Some analogous quinolines were prepared similarly.When tested for antimalarial activity against Plasmodium falciparum in vitro, the quinazolines were rather less active than the corresponding quinolines.