82256-09-5

Upstream product

• 4743-17-3 5-Chloroisatoic anhydride 
• 104-87-0 4-methyl-benzaldehyde 
• 106-47-8 4-chloro-aniline 
• 104-85-8 para-methylbenzonitrile 
• 635-21-2 5-chloroanthranilic acid 
• 1030524-56-1 6-chloro-2-(p-tolyl)-4H-benzo[d][1,3]oxazin-4-one 
• 104-81-4 4-Methylbenzyl bromide 
• 5202-85-7 2-Amino-5-chlorobenzamide 
• 21739-93-5 2-bromo-5-chlorobenzoic acid 
• 6326-27-8 p-methylbenzamidine hydrochloride 
• 104-84-7 para-methylbenzylamine 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 766-97-2 4-n-methylphenylacetylene 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 1246524-02-6 6-chloro-2-p-tolylquinazolin-4(3H)-thione 
• 1246524-05-9 6-chloro-4-hydrazinyl-2-p-tolylquinazoline 
• 1609338-18-2 9-chloro-5-p-tolyltetrazolo[1,5-c]quinazoline 
• 1609338-19-3 9-chloro-5-p-tolyl-[1,2,4]triazolo[4,3-c]quinazoline-3-thiol 

Relevant academic research and scientific papers

Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generatedin situ viaC=C bond cleavage

This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various aminobenzamides andin situ-generated aldehydes. The latter was formedviaC=C bond cleavage, and the overall reaction proceeded using molecular oxygen as a clean oxidant in the absence of a photocatalyst. Visible light, which was indispensable for the entire course of the reaction, played multiple roles. It initially cleaved styrene to an aldehyde, then facilitated its cyclization with ano-substituted aniline, and finally promoted the dehydrogenation of the cyclized intermediate. The previous step provided the feedstock for the next step in the reaction, thereby preventing volatilization, oxidation, and polymerization of the aldehyde. Thus, the overall process is simple, environmentally benign, and economically feasible.

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

Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis

A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.

Solvent-free copper-catalyzed three-component synthesis of 2-substituted quinazolin-4(3H)-ones

Abstract: A novel and efficient approach for the synthesis of quinazoline-4(3H)-ones through a one-pot copper-catalyzed three-component reaction of isatoic anhydrides, aryl nitriles, and ammonium acetate under solvent-free conditions in good yields is described. Graphical abstract: [Figure not available: see fulltext.]

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.

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

Design, synthesis and biological evaluation of some novel substituted quinazolines as antitumor agents

A novel series of 6-chloro-2-p-tolylquinazolinone and substituted-(4- methylbenzamido)benzamide (1-20) were designed, synthesized and evaluated for their in-vitro antitumor activity. Compounds 3, 14 and 16 possessed remarkable broad-spectrum antitumor activity. Compound 16 was found to be a particularly active growth inhibitor of the renal cancer (GI50 = 4.07 μM), CNS cancer (GI50 = 7.41 μM), ovarian cancer (GI50 = 7.41 μM) and non-small cell lung cancer (GI50 = 7.94 μM). Compound 16 ranks as nearly 1.5-fold more potent (mean GI50 = 15.8 μM) compared to 5-FU (mean GI50 = 22.6 μM).

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

Copper-catalyzed domino synthesis of quinazolin-4(3 H)-ones from (Hetero)arylmethyl halides, bromoacetate, and cinnamyl bromide

Alkyl halides, including heteroarylmethyl and arylmethyl halides, bromoacetate, and cinnamyl bromide, are readily prepared via halogenation from basic raw materials, even using green processes. It is essential to replace their downstream products with them to prepare medicinally important heterocycles quinazolin-4(3H)-ones. Copper(I) bromide catalyzed domino reaction of alkyl halides and anthranilamides under air affords 2-substituted quinazolin-4(3H)-ones in good to excellent yields and with wide functional group tolerance. A mechanism for a copper(I) bromide involved organometal-catalyzed reaction via a four-step domino reaction is proposed. Georg Thieme Verlag Stuttgart New York.

Copper-catalyzed domino synthesis of quinazolinones via Ullmann-type coupling and aerobic oxidative C-H amidation

An efficient copper-catalyzed approach to quinazolinone derivatives has been developed, and the protocol uses cheap and readily available substituted 2-halobenzamides and (aryl)methanamines as the starting materials as well as economical and environmentally friendly air as the oxidant. This can be the first example of constructing N-heterocycles via sequential Ullmann-type coupling under air and aerobic oxidative C-H amidation.