83800-83-3

Upstream product

• 455-18-5 4-CF₃C₆H₄CN 
• 76854-95-0 2-amino-N,N-diethylbenzamide 
• 118-92-3 anthranilic acid 
• 201230-82-2 carbon monoxide 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 28144-70-9 anthranilic acid amide 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 1885-29-6 anthranilic acid nitrile 
• 402-49-3 4-bromomethyltrifluoromethylbenzene 
• 6140-17-6 4-methylbenzotrifluoride 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 1072-85-1 o-fluorobromobenzene 
• 38980-96-0 4-(trifluoromethyl)benzimidamide hydrochloride 

Downstream Products

• 1041568-57-3 2-(p-trifluoromethylphenyl)-4-chloroquinazoline 
• 1448068-50-5 C₁₆H₁₀F₃N₅ 
• 1448069-08-6 2-(4-trifluoromethylphenyl)-3H-quinazoline-4-thione 
• 1448068-61-8 C₁₅H₁₁F₃N₄ 

Relevant academic research and scientific papers

Palladium-catalyzed one-pot synthesis of 2-substituted quinazolin-4(3H)-ones fromo-nitrobenzamide and alcohols

Palladium-catalyzed 2-substituted quinazolin-4(3H)-one formation from readily availableo-nitrobenzamides and alcohols using hydrogen transfer is described. Various quinazolin-4(3H)-ones were obtained in good to high yields. The cascade reaction including

Metal-free catalyst for the visible-light-induced photocatalytic synthesis of quinazolinones

In the present work, we have developed a novel and environmentally friendly method for the synthesis of quinazolinones using fluorescein as a photocatalyst via a condensation reaction of o-aminobenzamides and aldehydes under visible light irradiation. In this protocol, neither toxic oxidants nor transition-metal catalysts were needed, and a series of quinazolinones could be obtained in high efficiencies. In addition, this reaction can be extended to gram levels and has a large potential of wide application in future industrialization.

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes have been developed. In this protocol, a variety of nitriles as well as aldehydes react with 2-substituted benzamides to corresponding quinazolin-4(3H)-ones products in good to moderate yields, via the cleavage of C-X and C-N bonds and the formation of double C-N bonds simultaneously, in presence of potassium tert-butoxide.

Three-Component Couplings among Heteroarenes, Difluorocyclopropenes, and Water via C-H Activation

Three-component couplings have been realized for efficiently constructing various nitrogen-containing skeletons via C-H activation, where difluorocyclopropenes have been first identified as coupling partners. Many substrates including sp2 and sp3 C-H substrates were well tolerated, furnishing the corresponding products in good yields. Furthermore, a catalyst-dependent reaction was also developed, enabling divergent construction of two different frameworks. The application value of these reactions was demonstrated in gram-scale experiments with as little as 1 mol % catalyst.

Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach

Herein we report an exclusively ligand-centered redox controlled approach for the dehydrogenation of a variety of N-heterocycles using a Zn(II)-stabilized azo-anion radical complex as the catalyst. A simple, easy-to-prepare, and bench-stable Zn(II)-complex (1b) featuring the tridentate arylazo pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline, in the presence of zinc-dust, undergoes reduction to form the azo-anion radical species [1b]- which efficiently dehydrogenates various saturated N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-one, and 1,2,3,4-tetrahydro-2-phenylquinazolines, among others, under air. The catalyst has further been found to be compatible with the cascade synthesis of these N-heterocycles via dehydrogenative coupling of alcohols with other suitable coupling partners under air. Mechanistic investigation reveals that the dehydrogenation reactions proceed via a one-electron hydrogen atom transfer (HAT) pathway where the zinc-stabilized azo-anion radical ligand abstracts the hydrogen atom from the organic substrate(s), and the whole catalytic cycle proceeds via the exclusive involvement of the ligand-centered redox events where the zinc acts only as the template.

Iron catalyzed metal-ligand cooperative approaches towards sustainable synthesis of quinolines and quinazolin-4(3H)-ones

Herein we report simple, efficient, and economically affordable metal-ligand cooperative strategies for synthesizing quinolines and quinazolin-4(3H)-ones via dehydrogenative functionalization of alcohols. Various polysubstituted quinolines and quinazolin-4(3H)-ones were prepared in good yields via dehydrogenative coupling of readily available alcohols with ketones and 2-aminobenzamides, respectively under air using a well-defined Fe(II)-catalyst, ([FeL1Cl2] (1)) bearing a redox-active azo-aromatic pincer 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline) (L1). Control experiments and mechanistic investigation disclose that the one-electron reduced mono-anionic species [1]? bearing an iron-stabilized azo-anion radical ligand catalyzes these reactions. Both iron and the redox-active arylazo ligand participate synergistically during the different steps of these catalytic reactions.

Ruthenium(II)-catalyzed C?C/C?N coupling of 2-arylquinazolinones with vinylene carbonate: Access to fused quinazolinones

In this work, ruthenium(II)-catalyzed C?C/C?N annulation of 2-arylquinazolinones with vinylene carbonate is reported to synthesize fused quinazolinones. This catalytic system tolerates a wide range of substrates with excellent functional-group compatibility. In this transformation, the vinylene carbonate acts as an ethynol surrogate without any external oxidant involved. Furthermore, preliminary mechanistic studies were conducted, and a plausible catalytic cycle was also proposed.

Method for synthesizing 2 -phenylquinazolone compound by taking styrene compound as raw material

The invention discloses a method for synthesizing a 2-phenyl quinazolinone compound. The method comprises the steps of adopting a styrene compound and 2-aminobenzamide as reaction raw materials; underthe combined action of a palladium catalyst, a ligand and oxygen, reacting to obtain the 2-phenyl quinazolinone compound, wherein the reaction temperature is 80 DEG C to 110 DEG C, a reaction formulais as shown in the below figure, and R is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, nitro or methoxyl. The method provided by the invention has the beneficial effects that the raw material styrene compound is cheap and easy to get, so that the method is more economical; a preparation method is simple and convenient to operate, and the obtained product is easy to post-process, so that the method is suitable for large-scale industrial production; no high temperature and high pressure is needed, and a reaction condition is mild; the method is short in reaction time, high efficient to react, high in yield, and higher in reaction efficiency after reaction amplification.

Synthesis of quinazolin-4(3H)-ones via electrochemical decarboxylative cyclization of α?keto acids with 2-aminobenzamides

Herein, an environmentally benign electrochemical protocol has been disclosed for the synthesis of quinazolin-4(3H)-one derivatives from readily available α?keto acids and 2-aminobenzamides. This decarboxylative cyclization process proceeds conveniently in the absence of any homogeneous metal catalysts, bases, or external oxidants. This protocol also features CO2 by-products, mild reaction conditions (room temperature and air atmosphere), and a wide variety of substrate scope, including an array of 2,3-disubstituted quinazolinone products.

Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst

Herein, we report a bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and anin situgenerated non-native secondary amine. The catalyst consists of ano-quinone cofactor phd (1,10-phenanthroline-5,6-dione) and a copper ion and operates under ambient air conditions. Quinazolin-4(3H)-ones, which are common pharmacophores present in numerous pharmaceuticals and bioactive compounds, were synthesized in high yields. A detailed kinetic and mechanistic study elucidates the role of the catalyst in the multi-step oxidative cascade reaction.