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Upstream product

• 2142-69-0 2-bromophenyl methyl ketone 
• 104-87-0 4-methyl-benzaldehyde 
• 589-18-4 4-Methylbenzyl alcohol 
• 577-59-3 2-acetylnitrobenzene 
• 551-93-9 2-aminoacetophenone 
• 104-84-7 para-methylbenzylamine 
• 872-36-6 vinylene carbonate 
• 7118-55-0 4-methyl-N-phenylbenzimidamide 
• 941706-81-6 1-(2-aminophenyl)ethanol 
• 104-85-8 para-methylbenzonitrile 
• 6326-27-8 p-methylbenzamidine hydrochloride 
• 18818-41-2 2-(4-methylphenyl)-4(3H)-quinazolinone 
• 3385-78-2 trimethyl indium 

Relevant academic research and scientific papers

Vinylene carbonate: Beyond the ethyne surrogate in rhodium-catalyzed annulation with amidines toward 4-methylquinazolines

In this paper, we developed a rhodium-catalyzed annulation of vinylene carbonate with amidines, leading to 4-methylquinazolines with moderate to excellent yields. This procedure proceeded by sequentialortho-acylation and annulation, where vinylene carbonate served as the acetylation reagent rather than the ethyne surrogate.

Synthesis of Quinazoline and Quinazolinone Derivatives via Ligand-Promoted Ruthenium-Catalyzed Dehydrogenative and Deaminative Coupling Reaction of 2-Aminophenyl Ketones and 2-Aminobenzamides with Amines

The in situ formed ruthenium catalytic system ([Ru]/L) was found to be highly selective for the dehydrogenative coupling reaction of 2-aminophenyl ketones with amines to form quinazoline products. The deaminative coupling reaction of 2-aminobenzamides with amines led to the efficient formation of quinazolinone products. The catalytic coupling method provides an efficient synthesis of quinazoline and quinazolinone derivatives without using any reactive reagents or forming any toxic byproducts.

Visible-Light-Induced Benzylic C-H Functionalization for the Synthesis of 2-Arylquinazolines

This work reports a mild and efficient approach for the synthesis of substituted quinazolines using 1-(2-aminoaryl)ethan-1-ones in conjunction with arylmethanamines as starting materials via visible-light-induced benzylic C–H functionalization. The reaction proceeded at room temperature with low catalyst loading and the reaction system was clean from beginning to end. Significantly, this method exhibited good tolerance even to free hydroxyl group and amino group contained in substrates.

Accessing Polysubstituted Quinazolines via Nickel Catalyzed Acceptorless Dehydrogenative Coupling

Two environmentally benign methods for the synthesis of quinazolines via acceptorless dehydrogenative coupling of 2-aminobenzylamine with benzyl alcohol (Path A) and 2-aminobenzylalcohol with benzonitrile (Path B), catalyzed by cheap, earth abundant and easy to prepare nickel catalysts, containing tetraaza macrocyclic ligands (tetramethyltetraaza[14]annulene (MeTAA) or 6,15-dimethyl-8,17-diphenyltetraaza[14]annulene (MePhTAA)) are reported. A wide variety of substituted quinazolines were synthesized in moderate to high yields starting from cheap and easily available starting precursors. A few control reactions were performed to understand the mechanism and to establish the acceptorless dehydrogenative nature of the catalytic reactions.

Maximizing the Catalytic Activity of Nanoparticles through Monolayer Assembly on Nitrogen-Doped Graphene

We report a facile method for assembly of a monolayer array of nitrogen-doped graphene (NG) and nanoparticles (NPs) and the subsequent transfer of two layers onto a solid substrate (S). Using 3 nm NiPd NPs as an example, we demonstrate that NiPd-NG-Si (Si=silicon wafer) can function as a catalyst and show maximum NiPd catalysis for the hydrolysis of ammonia borane (H3NBH3, AB) with a turnover frequency (TOF) of 4896.8 h?1 and an activation energy (Ea) of 18.8 kJ mol?1. The NiPd-NG-S catalyst is also highly active for catalyzing the transfer hydrogenation from AB to nitro compounds, leading to the green synthesis of quinazolines in water. Our assembly method can be extended to other graphene and NP catalyst materials, providing a new 2D NP catalyst platform for catalyzing multiple reactions in one pot with maximum efficiency.

AgPd Nanoparticles Deposited on WO2.72 Nanorods as an Efficient Catalyst for One-Pot Conversion of Nitrophenol/Nitroacetophenone into Benzoxazole/Quinazoline

We report a seed-mediated growth of 2.3 nm AgPd nanoparticles (NPs) in the presence of 40 × 5 nm WO2.72 nanorods (NRs) for the synthesis of AgPd/WO2.72 composites. The strong interactions between AgPd NPs and WO2.72 NRs make the composites, especially the Ag48Pd52/WO2.72, catalytically active for dehydrogenation of formic acid (TOF = 1718 h-1 and Ea = 31 kJ/mol) and one-pot reactions of formic acid, 2-nitrophenol, and aldehydes into benzoxazoles in near quantitative yields under mild conditions. The catalysis can also be extended to the one-pot reactions of ammonium formate, 2-nitroacetophenone, and aldehyde for high yield syntheses of quinazolines. Our studies demonstrate a new catalyst design to achieve a green chemistry approach to one-pot reactions for the syntheses of benzoxazoles and quinazolines.

Ultrasound-Assisted Preparation of Copper(I) Oxide Nanocubes: High Catalytic Activity in the Synthesis of Quinazolines

A facile and green ultrasound-assisted synthesis of Cu2O nanocubes at room temperature is presented. The Cu2O nanocubes were characterized using XRD, SEM, TEM, energy-dispersive X-ray spectroscopy, UV/Vis spectroscopy, differential scanning calorimetry with thermogravimetric analysis, and FTIR spectroscopy. The Cu2O nanocubes were employed as a heterogeneous nanocatalyst and were found to be highly active in the preparation of quinazolines by the tandem cyclization of 2-bromobenzaldehydes with amidines under ligand-free conditions. Various quinazolines could be prepared in excellent yields within a very short reaction time. Furthermore, the Cu2O nanocatalyst could be recycled and reused up to four times without any significant loss of catalytic activity.

Palladium-Catalyzed Cross-Coupling of 4-Tosyloxyquinazolines with Organoindium Reagents: An Efficient Route to 4-Substituted Quinazolines

An efficient route to 4-substituted quinazolines by arylation or alkylation of quinazolinones under mild conditions is described. 4-Tosyloxyquinazolines were obtained through the reaction of quinazolinones and p-methylbenzenesulfonyl chloride in the presence of K2CO3. The cross-coupling reaction of 4-tosyloxyquinazolines with organoindium reagents, carried out in tetrahydrofuran, catalyzed by Pd2(dba)3/ (2-furyl)3P led to the formation of 4-functionalized quinazolines in good to excellent yields. Higher yields were obtained by the one-pot reaction of quinazolinone, p-methylbenzenesulfonyl chloride, Pd2(dba)3-/(2-furyl)3P, and organoindium reagent. These methods using organoindium compounds as coupling partners provided an efficient route to 4-(hetero)aryl/alkylquinazolines, especially 4-substituted quinazolines bearing a halogen scaffold.

Heterogeneous Palladium-Catalyzed Hydrogen-Transfer Cyclization of Nitroacetophenones with Benzylamines: Access to C?N Bonds

The first Pd/C-catalyzed oxidative C(sp3)?H bond amination of o-nitroacetophenones with benzylamines or amino acids proceeding through C?N bond cleavage followed by C?N bond formation by a hydrogen-transfer strategy was developed. These transformations proceeded smoothly in water to afford the desired quinazolines in moderate to good yields. This protocol has a broad substrate scope and good tolerance of air, offers excellent recyclability of the catalyst, and does not need any additional oxidant, ligand, or base; the combination of all of these factors give a new and practical avenue for multiple C?N bond formation. Moreover, a hot filtration experiment indicated that heterogeneous palladium nanoparticles during the reaction are the active species.

Expanding applications of zeolite imidazolate frameworks in catalysis: Synthesis of quinazolines using ZIF-67 as an efficient heterogeneous catalyst

A cobalt zeolite imidazolate framework (ZIF-67) was successfully synthesized and characterized by several techniques. The ZIF-67 was used as an efficient heterogeneous catalyst for the cyclization reaction of 2-aminobenzoketones and benzylamine derivatives to form quinazoline products. The optimal conditions involved the use of TBHP oxidant in toluene solvent at 80°C. Remarkably, the ZIF-67 catalyst exhibited better performance in the cyclization reaction than common cobalt salts such as Co(NO3)2, CoCl2, and Co(OAc)2 and other Co-MOFs such as ZIF-9, Co-MOF-74, and Co2(BDC)2(DABCO). In addition, the cyclization reaction could only proceed in the presence of the solid Co-ZIF catalyst and there was no contribution from leached active sites present in the solution. The catalyst could be recovered and reused several times without a significant degradation in catalytic activity.