27131-17-5

Basic information

• Product Name: 2-(2-methoxyphenyl)-quinazoline
• Synonyms: 2-(2-methoxyphenyl)-quinazoline
• CAS NO: 27131-17-5
• Molecular Weight: 236.273
• Mol File: 27131-17-5.mol

Chemical Properties

• CAS DataBase Reference: 2-(2-methoxyphenyl)-quinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-methoxyphenyl)-quinazoline(27131-17-5)
• EPA Substance Registry System: 2-(2-methoxyphenyl)-quinazoline(27131-17-5)

Safety Data

• Hazardous Substances Data: 27131-17-5(Hazardous Substances Data)

Upstream product

• 26260-02-6 2-iodobenzaldehyde 
• 57075-83-9 2-methoxybenzene-1-carboximidamide hydrogenchloride 
• 135-02-4 ortho-anisaldehyde 
• 4403-69-4 2-amino-1-benzylamine 
• 2439-77-2 2-methoxybenzamide 
• 3959-05-5 2-bromobenzylamine 
• 6609-56-9 2-methoxy-benzonitrile 
• 100-46-9 benzylamine 
• 612-25-9 2-Nitrobenzyl alcohol 
• 93-25-4 2-methoxyphenylacetic acid 
• 5344-90-1 2-Aminobenzyl alcohol 
• 6850-57-3 2-methoxybenzylamine 
• 107369-63-1 2-methoxybenzaldehyde O-methyloxime 
• 84571-05-1 2-(2-methoxyphenyl)-1,2,3,4-tetrahydroquinazoline 

Relevant articles and documents

Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air

By using air as the superior oxidant, a highly atom-efficient synthesis of 2-substituted quinazolines is developed by a CsOH-mediated direct aerobic oxidative reaction of the readily available and stable 2-aminoarylmethanols and nitriles. Effectively working as the promoter in the alcohol oxidation, nitrile hydration, and cyclocondensation steps, CsOH is the best base for the reaction. A similar method can also be extended to the synthesis of substituted quinolines starting from methyl ketones instead of nitriles.

Copper (II) complex supported on the surface of magnetic nanoparticles modified with S-benzylisothiourea (Fe3O4@SiO2-SMTU-Cu): A new and efficient nanomagnetic catalyst for the synthesis of quinazolines and amides

A novel magnetically recoverable copper catalyst was successfully fabricated through the immobilization of Cu(NO3)2 on the surface of silica-coated magnetic Fe3O4 nanoparticles (Fe3O4@SiO2) functionalized with S-benzylisothiourea ligand. The Fe3O4@SiO2-SMTU-Cu nanocomposite was fully characterized by FT-IR spectroscopy, SEM, EDX, TGA, XRD, VSM, ASS and ICP-OES techniques. The Fe3O4@SiO2-SMTU-Cu nanocomposite exhibited high catalytic activity in the synthesis of biologically active quinazolines and amides. According to our research on the literature, this is the first report in the use of magnetic copper nanocatalyst for the synthesis of quinazolines. In this paper, we also presented tentative mechanisms for the synthesis of quinazolines and amides in the presence of catalytic amount of Fe3O4@SiO2-SMTU-Cu nanocomposite. This method gives notable advantages such as easy separation of the catalyst by external magnetic field; excellent yields, short reaction times, nontoxic metal catalyst, and simplicity of operation make this method a facile tool for the synthesis of quinazolines and amides.

Nickel-Catalyzed [4 + 2] Annulation of Nitriles and Benzylamines by C-H/N-H Activation

Nickel-catalyzed [4 + 2] annulation of benzylamines and nitriles via C-H/N-H bond activation, providing straightforward atom-economic access to a wide variety of multisubstituted quinazolines, is reported. Mechanistic investigation revealed that the in situ formed amidines from the coupling of benzylamines and nitriles direct the nickel catalyst to activate the ortho-C-H bond of the phenyl ring of the benzylamine.

Sulfur-Mediated Decarboxylative Coupling of 2-Nitrobenzyl Alcohols and Arylacetic Acids

We report a new method for the synthesis of substituted quinazolines by the condensation of 2-nitrobenzyl alcohols with arylacetic acids. The transformation requires the use of urea as a nitrogen source, elemental sulfur as a promoter, DABCO as a base, and DMSO as a solvent. Functionalities such as chloro, fluoro, trifluoromethyl, thienyl, and indolyl groups were all compatible with the reaction conditions. Because our method uses stable simple substrates to obtain the N,N-heterocycles in the absence of transition metals, it offers a potential pathway for preparing complex structures under mild conditions.

Application of laccase/DDQ as a new bioinspired catalyst system for the aerobic oxidation of tetrahydroquinazolines and Hantzsch 1,4-dihydropyridines

Laccase/DDQ as a new bioinspired quinone-based cooperative catalytic system was used for the biomimetic aerobic oxidative synthesis of 2-substituted quinazolines and Hantzsch pyridines from the oxidative cyclocondensation of 2-aminobenzylamine and aldehyd

Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal-Free Catalyst under Air

Graphene oxide (GO) has been developed as an inexpensive, environmental friendly, metal-free carbocatalyst for the dehydrogenation of nitrogen heterocycles. Valuable compounds, such as quinoline, 3,4-dihydroisoquinoline, quinazoline, and indole derivatives, have been successfully used as substrates. The investigation of various oxygen-containing molecules with different conjugated systems indicated that both the oxygen-containing groups and large π-conjugated system in GO sheets are essential for this reaction. (Figure presented.).

Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: Synthesis of quinazolines by trapping of ammonia

A novel approach to construct 2-aryl/heteroaryl quinazolines was developed through an iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines under aerobic oxidative conditions. The reaction proceeds via the formation of N-benzylideneb

Synthesis of 2-aryl quinazolines from (2-aminophenyl)methanol and oxime ether catalyzed by copper ferrite nanoparticles

Magnetically separable copper ferrite nps as a catalytic system, under solvent free reaction condition for synthesis of 2-arylquinazolines has been reported. (2-aminoaryl)methanols and various types of oxime ethers were efficiently converted into desired products in moderate to good yields. This protocol offers a greener and atom efficient process, using recyclable heterogeneous catalytic system.

Synthesis method for 2-substituted quinazoline heterocyclic compound

The invention discloses a synthesis method for a 2-substituted quinazoline heterocyclic compound. According to the efficient synthesis method, 2-aminobenzylalcohol and nitrile are subjected to an oxidation-cyclization reaction in air under the alkaline condition to prepare the 2-substituted quinazoline heterocyclic compound. By means of the method, no transition metal catalyst or ligand is needed, and the reaction is directly carried out through heating under the alkaline condition to obtain the 2-substituted quinazoline heterocyclic compound. The reaction condition is simple, operation is easy, air serves as an economical, safe and environment-friendly catalyst, a by-product is water, and atom efficiency is high. The requirement of the method for the reaction condition is low, and the method has certain research and industrial application prospects.

Highly efficient one-pot synthesis of 2-substituted quinazolines and 4H-benzo[d][1,3]oxazines via cross dehydrogenative coupling using sodium hypochlorite

This communication describes a catalyst-free synthesis of 2-substituted quinazolines and 4H-benzo[d][1,3]oxazines using commericially available sodium hypochlorite as oxidant. Operational simplicity, mild reaction conditions and the ability to construct structurally diverse 2-quinazolines and 2-substituted 4H-benzo[d][1,3]oxazines by this method render it to be a practical alternative for the synthesis of these heterocycles.