82256-07-3

Upstream product

• 82255-97-8 N-ethoxycarbonyl-N'-(4-methylphenyl)-4-methylbenzamidine 
• 57774-66-0 N-(Ethoxycarbonyl)-4-methylbenzenethiocarboxamide 
• 6967-82-4 2-bromo-5-methylbenzoic acid 
• 6326-27-8 p-methylbenzamidine hydrochloride 
• 40545-33-3 2-amino-5-methylbenzamide 
• 104-87-0 4-methyl-benzaldehyde 
• 624-31-7 4-tolyl iodide 
• 144-62-7 oxalic acid 
• 104-84-7 para-methylbenzylamine 
• 4498-99-1 4-methylbenzylthiol 
• 589-18-4 4-Methylbenzyl alcohol 
• 37795-77-0 6-methoxy-2H-3,1-benzoxazine-2,4(1H)-dione 
• 959031-87-9 N-(2-iodo-4-methylphenyl)-4-methylbenzamide 
• 2941-78-8 2-Amino-5-methylbenzoic acid 

Relevant academic research and scientific papers

A highly efficient heterogeneous copper-catalyzed cascade reaction of 2-halobenzoic acids and amidines leading to quinazolinones

The heterogeneous cascade reaction of 2-halobenzoic acids and amidines was achieved in DMF at 60 °C in the presence of 10 mol% of MCM-41-immobilized tridentate nitrogen copper(i) complex [MCM-41-3N-CuI] using Cs2CO3 as base, yielding a variety of quinazolinone derivatives in good to excellent yields. This heterogeneous copper catalyst can be easily prepared from commercially available and inexpensive reagents, and recovered by a simple filtration of the reaction solution and reused for at least 10 times without any decreases in activity. This journal is

An efficient transition-metal-free route to quinazolin-4(3H)-onesvia2-aminobenzamides and thiols

An efficient approach to quinazolin-4(3H)-ones was developed by a one-pot intermolecular annulation reaction ofo-amino benzamides and thiols. This method has the features of good functional group tolerance, being transition metal and external oxidant free, and easy operation. Varieties of 2-aryl (heteroaryl) quinazolin-4(3H)-one, 2-phenyl-pyrido[2,3-d]pyrimidin-4(3H)-one and 3-phenyl-2H-1,2,4-benzo thiadiazine-1,1-dioxide derivatives were obtained with a yield of up to 98%. The control experiment revealed that the thiol substrate could promote the dehydroaromatization step.

Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2-Aryl Quinazolinones Utilizing the π-Benzylpalladium(II) System in Water

We demonstrate the direct use of benzylic alcohols for a multicomponent reaction of readily available isatoic anhydrides with amines in water, which is a synthetic route for the direct construction of a series of 2-aryl quinazolinones. This one-pot synthetic method involves the dehydrative N-benzylation of in situ generated anthranilamides followed by an amide-directed benzylic C?H amination process utilizing the π-benzylPd(II) system. Comparison of independent rate measurements using benzyl alcohol and its deuterated form gave a kinetic isotope effect of 3.5. Therefore, the benzylic C?H bond is cleaved in the rate-determining step. We successfully carried out a gram-scale reaction in 85% yield with simplified product isolation. (Figure presented.).

Pd/C Catalyzed Cascade Synthesis of 2-Arylquinazolinones from 2-Iodoacetanilides Employing Ammonia and CO Precursors

An efficient and straightforward approach has been demonstrated for 2-aryl quinazolinones synthesis from 2-iodoacetanilides using ammonium carbamate/ammonium carbonate and oxalic acid under heterogeneous Pd/C catalyzed conditions. Herein, we have carried

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

Polystyrene-Supported Palladium (Pd?PS)-Catalyzed Carbonylative Annulation of Aryl Iodides Using Oxalic Acid as a Sustainable CO Source for the Synthesis of 2-Aryl Quinazolinones

An efficient and convenient strategy for the synthesis of diversely substituted quinazolinones from o-carbamoyl/cyano aniline and aryl iodides using oxalic acid as a CO source under polystyrene supported palladium (Pd?PS) nanoparticles (NPs) catalyzed con

Structure-activity relationships of 2-arylquinazolin-4-ones as highly selective and potent inhibitors of the tankyrases

Tankyrases (TNKSs), members of the PARP (Poly(ADP-ribose)polymerases) superfamily of enzymes, have gained interest as therapeutic drug targets, especially as they are involved in the regulation of Wnt signalling. A series of 2-arylquinazolin-4-ones with varying substituents at the 8-position was synthesised. An 8-methyl group (compared to 8-H, 8-OMe, 8-OH), together with a 4′-hydrophobic or electron-withdrawing group, provided the most potency and selectivity towards TNKSs. Co-crystal structures of selected compounds with TNKS-2 revealed that the protein around the 8-position is more hydrophobic in TNKS-2 compared to PARP-1/2, rationalising the selectivity. The NAD+-binding site contains a hydrophobic cavity which accommodates the 2-aryl group; in TNKS-2, this has a tunnel to the exterior but the cavity is closed in PARP-1. 8-Methyl-2-(4-trifluoromethylphenyl)quinazolin-4-one was identified as a potent and selective inhibitor of TNKSs and Wnt signalling. This compound and analogues could serve as molecular probes to study proliferative signalling and for development of inhibitors of TNKSs as drugs.

Metal-free one-pot synthesis of 1,3-diazaheterocyclic compounds via I2-mediated oxidative C-N bond formation

A one-pot I2-mediated annulation reaction of substrates containing diamino groups and aldehydes has been developed via oxidative C-N bond formation. This general and environmentally benign synthetic approach provides facile access to a variety of 1,3-diazaheterocyclic compounds, including quinazolinones, benzimidazoles, and cyclic amidines.

Synthesis of 2-arylquinazolin-4(3H)-ones by N-aryl benzamidines with aromatic carbonates

The reaction of N-aryl benzamidines 1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h, 1i, 1j, 1k, 1l, 1m, 1n with diphenyl carbonate 2a or ethyl phenyl carbonate 2b synthesized 2-arylquinazolin-4(3H)-ones 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3m, 3n in simple and

Catalyst/ligand-free synthesis of benzimidazoles and quinazolinones from amidines via intramolecular transamination reaction

An efficient catalyst/ligand-free synthesis of benzimidazoles and quinazolinones from amidines in quantitative yields has been described.