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Usage

Uses

Used in Pharmaceutical Industry:
Quinazoline is used as a basic structural unit for the synthesis of pharmaceuticals, particularly antitumor drugs, due to its significant role in modern drug development.
Used in Electrochemistry Research:
Quinazoline is used in the study of electrochemical behavior using modern polarographic and voltammetric methods, which helps in understanding its properties and potential applications in various fields.
Used in Medicinal Chemistry:
Quinazoline is used as a key component in the development of drugs with antibacterial, antifungal, anticonvulsant, anti-inflammatory, and antitumor activities, making it a valuable compound in medicinal chemistry.

Biochem/physiol Actions

Genotoxicity of quinazoline was established by bacterial SOS Chromotest (Escherichia Coli).

Purification Methods

Purify quinazoline by passage through an activated alumina column in *C6H6 or pet ether (b 40-60o). Distil it under reduced pressure, sublime it under vacuum and crystallise it from pet ether. The picrate has m 188-189o (from MeOH). [Armarego J Appl Chem 11 70 1961, Armarego Quinazolines, Fused Pyrimidines Part I Brown Ed, Wiley-Interscience 1967, Brown Quinazolines Supplement I Taylor Ed, Wiley-Interscience 1996, ISBN 0-471-14565-3; for covalent hydration see Albert & Armarego Adv Heterocycl Chem 4 1 1965, Beilstein 23 H 175, 23 II 177, 23 III/IV 1221.]

InChI:InChI=1/C8H6N2/c1-2-4-8-7(3-1)5-9-6-10-8/h1-6H

Upstream product

• 631-61-8 ammonium acetate 
• 529-23-7 o-aminobenzaldehyde 
• 91085-79-9 N,N'-(2-nitro-benzylidene)-bis-formamide 
• 94447-50-4 3-acetyl-3,4-dihydro-4-hydroxyquinazoline 
• 55276-59-0 (4-chloro-phenyl)-quinazolin-4-yl-methanone 
• 55326-11-9 2-anisyl-4-quinazolinyl ketone 
• 151-50-8 potassium cyanide 
• 187336-04-5 4-(α-benzyl-α-hydroxybenzyl)quinazoline 
• 187336-16-9 1-(4-methoxyphenyl)-1-(quinazolin-4-yl)ethanol 
• 187336-17-0 1-Furan-2-yl-2-phenyl-1-quinazolin-4-yl-ethanol 
• 187336-14-7 1-(4-methoxyphenyl)-2-phenyl-1-(quinazoline-4-yl)ethanol 
• 1904-64-9 3,4-dihydroquinazoline 
• 64-19-7 acetic acid 
• 186030-01-3 N-(2-benzaldehyde)oxamic acid ethyl ester 

Downstream Products

• 32907-43-0 quinazoline-N-oxide 
• 491-36-1 4-Hydroxyquinazoline 
• 1904-65-0 1,2,3,4-tetrahydroquinazoline 
• 7556-95-8 6-nitro-quinazoline 
• 2217-31-4 3-ethyl-2(1H)-quinolinone 
• 5661-06-3 2,3-dihydro-1H-cyclopenta[b]quinoline 
• 104548-11-0 4-cyano-3-(2-chloromethylbenzoyl)-3,4-dihydroquinazoline 
• 126994-63-6 1,3-di(o-chloromethylbenzoyl)-2,4-dicyano-1,2,3,4-tetrahydroquinazoline 
• 76051-73-5 4-cyano-3,4-dihydroquinazoline hydrochloride 
• 76051-72-4 2,4-dicyano-1,3-dibenzoyl-1,2,3,4-tetrahydroquinazoline 
• 98512-42-6 4-(3-phenylpropyl)quinazoline 
• 59-31-4 2-quinolone 
• 94447-50-4 3-acetyl-3,4-dihydro-4-hydroxyquinazoline 
• 126994-67-0 1,3-dicinnamoyl-2,4-dicyano-1,2,3,4-tetrahydroquinazoline 

Relevant academic research and scientific papers

Hydrogenation/dehydrogenation of N-heterocycles catalyzed by ruthenium complexes based on multimodal proton-responsive CNN(H) pincer ligands

Ru complexes based on lutidine-derived pincer CNN(H) ligands having secondary amine side donors are efficient precatalysts in the hydrogenation and dehydrogenation of N-heterocycles. Reaction of a Ru-CNN(H) complex with an excess of base produces the formation of a Ru(0) derivative, which is observed under catalytic conditions.

Cu@U-g-C3N4 Catalyzed Cyclization of o-Phenylenediamines for the Synthesis of Benzimidazoles by Using CO2 and Dimethylamine Borane as a Hydrogen Source

Abstract: This work reports a green and sustainable route for the synthesis of benzimidazoles via C–N bond formation using carbon dioxide (CO2) as a C1 carbon source. In this work, Cu@U-g-C3N4 catalyst was prepared from urea derived porous graphitic carbon?nitride (U-g-C3N4) and CuCl2 and characterized by FT-IR, XRD, XPS, SEM, TPD etc. The Cu@U-g-C3N4 as a heterogeneous recyclable catalyst has been employed first time for the cyclization of o-phenylenediamines (OPD) with CO2 to benzimidazoles using dimethylamine borane (DMAB). The proposed protocol becomes sustainable and efficient due to the use of propylene carbonate/water as a suitable biodegradable, economical and environmentally benign solvent system. The proposed catalytic system showed a wide range of substrate scope for the synthesis of benzimidazoles in good to excellent yields. Graphical Abstract: [Figure not available: see fulltext.]

Gold(0) catalyzed dehydrogenation of N-heterocycles

Gold nanoclusters are good catalyst precursors for the catalytic dehydrogenation of indolines, tetrahydroquinazolines, and related N-heterocycles. The catalytically active species is presumably Au(0) nanoparticles.

Oxalic/malonic acids as carbon building blocks for benzazole, quinazoline and quinazolinone synthesis

An oxidant, base and metal free methodology has been developed for the synthesis of various 2-substituted and non-substituted benzazoles, quinazolines and quinazolinones using oxalic/malonic acids as an in situ carbon source. This methodology is applicable for a wide range of substituted o-phenylenediamine, o-aminothiophenol, o-aminophenol and o-aminobenzamide containing various functional groups and provides good to excellent yields of the corresponding product. Furthermore an easy workup procedure, high yield and easy isolation of products are key features of this methodology. The developed protocol is also applicable for the gram scale synthesis of benzimidazoles.

Divergent Synthesis of Quinazolines Using Organocatalytic Domino Strategies under Aerobic Conditions

An easy and efficient organocatalytic approach to the synthesis of 2-substituted quinazolines is described based on the reaction between 2-aminobenzylamines and aldehydes or alcohols or amines. Three organocatalytic platforms were investigated, using 3-nitropyridine, pyridine N-oxide, and vitamin B3. Having established the new catalytic systems, the tandem transformations of 2-aminobenzylamines to give substituted quinazolines were achieved in excellent yields and with a broad substrate scope, with no formation of toxic side-products. The investigated conditions are not restricted to the use of aldehydes; the protocol also works well with alcohols or amines as substrates. These are oxidized in situ to the corresponding aldehydes to achieve the successful transformation. A mechanistic proposal has been drawn up based on control experiments. We found that under aerobic conditions, catalytic amounts of H2O2 can be generated; this plays a key role in the efficacy of the described approach. The green chemistry metrics of the developed method are also presented. The E factor of 8.18 mg/1 mg demonstrates that the reported method is an excellent complement to previous protocols.

The cascade synthesis of quinazolinones and quinazolines using an α-MnO2 catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant

Heterogeneously catalyzed synthesis of quinazolinones or quinazolines is reported in this study. An α-MnO2 catalyst is found to be highly active and selective in the oxidative cyclization of anthranilamides or aminobenzylamines with alcohols using TBHP as an oxidant. This protocol exhibits a broad substrate scope, and is operationally simple without an additive.

NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles

The pair NaBH4-TMEDA as hydride source and a palladium catalyst in THF prove to be an efficient system for the hydrodehalogenation of halogenated heterocycles with one or more heteroatoms. In general, Pd(OAc) 2-PPh3 rapidly hydrodehalogenates reactive halo-heterocycles such as bromo-pyridines, -quinolines, -thiophenes, -indoles, -imidazoles, etc., at room temperature in very good yields, whereas in most cases PdCl2(dppf) reduces less reactive halides such as chloro-pyridines, -quinolines, -pyrimidines and bromo-indoles, -benzofurans, etc. Moreover, PdCl2(tbpf) shows to be even more active removing the 2- and 5-chlorine from both thiophene and thiazole rings. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene and nitrile substituents. Moreover, with a proper selection of the catalyst it is also possible to obtain a good control in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.

Addition of α-lithiated nitriles to azaheterocycles

The addition of α-deprotonated nitriles to azaheteroA?-cycles followed by rearomatization is described. A simple two-step, one-pot procedure for the sequence is also presented. Georg Thieme Verlag Stuttgart New York.

A novel synthesis of quinazolines by cyclization of 1-(2-isocyanophenyl) alkylideneamines generated by the treatment of 2-(1-azidoalkyl)phenyl isocyanides with NaH

A new and efficient method for the synthesis of quinazolines has been developed. Thus, N-[2-(1-azidoalkyl)phenyl]formamides 1 are dehydrated with POCl3 to give the corresponding 2-(1-azidoalkyl)phenyl isocyanides 2, which are then treated with NaH in DMF at 0° to give quinazolines 6 in satisfactory yields via cyclization of 1-(2-isocyanophenyl)alkylideneamine intermediates 4. This methodology can be applied to the synthesis of the 7-azaanalogs of quinazolines, i.e., pyrido[3,4-d]pyrimidines 9. Copyright

Synthesis of quinazolines and tetrahydroquinazolines: Copper-catalyzed tandem reactions of 2-bromobenzyl bromides with aldehydes and aqueous ammonia or amines

An efficient synthesis of diversely substituted quinazolines and 1,2,3,4-tetrahydroquinazolines through copper-catalyzed tandem reactions of the readily available 2-bromobenzyl bromides, aldehydes, and aqueous ammonia or amines has been developed. By using ammonia and simple aliphatic amines as the nitrogen source, the present method provides a versatile and practical protocol for the synthesis of quinazolines and 1,2,3,4-tetrahydroquinazolines. Copper on the beat: An efficient, simple and economical synthesis of diversely substituted quinazolines and 1,2,3,4-tetrahydroquinazolines has been developed through copper-catalyzed tandem reactions of the readily available 2-bromobenzyl bromides, aldehydes, and aqueous ammonia or simple aliphatic amines. Copyright