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Upstream product

• 98-01-1 furfural 
• 28144-70-9 anthranilic acid amide 
• 1487-18-9 (furan-2-yl)ethylene 
• 617-89-0 furan-2-ylmethanamine 
• 527-69-5 2-furancarbonyl chloride 
• 54829-48-0 2-iodofuran 
• 201230-82-2 carbon monoxide 
• 610-15-1 2-nitrobenzamide 

Relevant academic research and scientific papers

Benign and efficient synthesis of 2-substituted 4(3H)-quinazolinones mediated by iron(III) chloride hexahydrate in refluxing water

Condensation of aldehydes with anthranilamide in refluxing water using iron(III) chloride hexahydrate as an oxidiant afforded 2-substituted 4(3H)-quinazolinones in good yields (77-93%). This method provides several advantages such as being environmentally friendly, having a simple work-up procedure, and affording high yields.

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.

Synthesis of Difluoromethyl-Substituted Quinazolines through Selective Difluoromethylation

A highly selective difluoromethylation of quinazolines has been achieved by using commercially available ethyl bromodifluoroacetate as difluorocarbene precursor, providing the corresponding difluoromethyl substituted quinazoline derivatives with up to 83% yield.

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.

A Metal- and Ligand-Free Synthesis of Quinazolin-4(3H)-ones via a Bu4NI/TBHP-Mediated Oxidative Cleavage of the Olefinic C=C Bond

Abstract: A metal and ligand-free protocol has been developed for the synthesis of quinazolin-4(3H)-ones in moderate to good yields from o-aminobenzamide and alkenes via a Bu4NI/TBHP-mediated oxidative cleavage of the C=C bond in alkenes.

Ortho -Naphthoquinone-catalyzed aerobic oxidation of amines to fused pyrimidin-4(3 H)-ones: A convergent synthetic route to bouchardatine and sildenafil

A facile access to fused pyrimidin-4(3H)-one derivatives has been established by using the metal-free ortho-naphthoquinone-catalyzed aerobic cross-coupling reactions of amines. The utilization of two readily available amines allowed a direct coupling strategy to quinazolinone natural product, bouchardatine, as well as sildenafil (Viagra) in a highly convergent manner. This journal is

Iridium(III)-Catalyzed Alkynylation of 2-(Hetero)arylquinazolin-4-one Scaffolds via C-H Bond Activation

The directed C-H alkynylation of 2-(hetero)arylquinazolin-4-ones has been explored with the ethynylbenziodoxolone reagent TIPS-EBX employing an Ir(III) catalyst. Complementary conditions for either monoalkynylation or dialkynylation have been developed. Also demonstrated is the broad scope of this reaction and the compatibility of various functional groups such as ?F, ?Cl, ?Br, ?CF3, ?OMe, ?NO2, and alkyl, etc.

Facile and solvent-free synthesis of quinazolin-4(3H)-ones under microwave condition promoted by SbCl3

– Antimony trichloride (SbCl3) was found to be an effective catalyst (1 mol%) for one-pot synthesis of quinazolin-4(3H)-ones in good to excellent yields using anthranilamide and acyl chlorides under microwave irradiation. This method has the advantages of simplicity, mild reaction conditions, highly tolerant to several functional groups, as well as the avoidance of hazardous solvents.

A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-aminobenzamides with aryl iodides leading to quinazolinones

The first heterogeneous carbonylative annulation of 2-aminobenzamides with aryl iodides was achieved in N,N-dimethylformamide (DMF) at 120 °C under 10 bar of carbon monoxide by using an MCM-41-immobilized bidentate phosphine palladium(II) complex [MCM-41-2P-Pd(OAc)2] as catalyst and 1,8-diazabicycloundec-7-ene (DBU) as base, yielding a wide variety of quinazolinone derivatives in good to excellent yields. The new heterogeneous palladium catalyst can easily be prepared by a simple procedure from commercially readily available reagents, and recovered by filtration of the reaction solution, and recycled up to eight times without significant loss of activity.

Bismuth-catalyzed synthesis of 2-substituted quinazolinones

The bismuth-catalyzed oxidative condensation of aldehydes with 2-aminobenzamide under aerobic conditions is reported using ethanol as the solvent. Good to excellent isolated yields (68–95%) of the corresponding 2-substituted quinazolinones were obtained under mild reaction conditions with excellent functional group tolerance. The quinazolinones were further functionalized to afford N-allylated quinazolinones, 2-aminopyridine derivatives, and annulated polyheterocyclic compounds via transition-metal catalyzed reactions.