- Palladium(II)-Catalyzed Three-Component Tandem Cyclization Reaction for the One-Pot Assembly of 4-Arylquinazolines
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A one-pot method for joining three separate components leading to an assortment of 4-arylquinazolines (27 examples) in good to excellent yields is described. The method consists of a palladium(II)-catalyzed?-cascade reaction involving C(sp)-C(sp 2/s
- Wang, Zijuan,Chen, Wenteng,He, Chang,Zhang, Guolin,Yu, Yongping
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p. 1356 - 1364
(2020/11/09)
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- “On-Water” Palladium-Catalyzed Tandem Cyclization Reaction for the Synthesis of Biologically Relevant 4-Arylquinazolines
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The quinazoline scaffold is prevalent in pharmaceutically relevant molecules that show diverse biological activities. Herein, we report an efficient “on-water” palladium-catalyzed tandem cyclization reaction from commercially available arylboronic acids and benzonitriles that enable the rapid access to 4-arylquinazoline scaffolds in good to excellent yields (45 examples, up to 98 % yield). This protocol has shown good functional group tolerance and broad substrate scope. The reaction was also performed on a gram scale and successfully applied to the synthesis of the highly potent and selective PI3Kδ inhibitor N11, showing the practicability and synthetic utility of the protocol. In this reaction, the quinazoline scaffold is efficiently constructed with the simultaneous formation of one C?C bond and one C?N bond. Collectively, the protocol could serve as an alternative strategy to synthesize biologically important quinazoline scaffolds.
- Yuan, Shuo,Yu, Bin,Liu, Hong-Min
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p. 13109 - 13113
(2019/10/22)
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- 4-arylquinazoline compounds and preparation method thereof
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The invention provides 4-arylquinazoline compounds which have a general formula as shown in the specification, wherein R represents hydrogen, halogen, alkane, nitro or alkoxy, R represents hydrogen or methyl, Ar represents groups as shown in the specification, and R represents hydrogen, halogen, alkane, alkoxy, nitro, hydroxy, trifluoromethyl, phenyl or methoxycarbonyl; the compounds enrich the structures of 4-arylquinazoline compounds, and provide a material basis for further study on the potential biological activity of the compounds. The invention also provides a preparation methodof the compounds, which comprises the following step: cyanophenyl raw materials react with aromatic phenylboronic acid ArB(OH)2 in a sealed environment under the action of a palladium salt catalyst,a bidentate chelating ligand, a Lewis acid and a solvent at 30-300 DEG C to form the 4-arylquinazoline compounds; a structural formula of the 4-arylquinazoline compounds is shown in the specification,and the preparation method provided by the invention has the advantages of no need of inert gas protection, mild reaction conditions, short reaction time, high yield and the like.
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Paragraph 0122-0125
(2019/09/17)
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- Copper-catalyzed oxidative amination of methanol to access quinazolines
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A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner. The reaction conditions are straightforward and highly atom economic to deliver the corresponding quinazolines in high yields with wide functional group tolerance. Importantly, the present method is applicable on a multigram scale and its synthetic utility is demonstrated by synthesizing quazodine, a muscle-relaxing drug in high yields.
- Satish, Gandhesiri,Polu, Ashok,Kota, Laxman,Ilangovan, Andivelu
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p. 4774 - 4782
(2019/05/24)
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- Silver-Catalyzed Isocyanide Insertion into N?H Bond of Ammonia: [5+1] Annulation to Quinazoline Derivatives
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A silver-catalyzed [5+1] annulation of o-acylaryl isocyanides with ammonium acetate and hydroxlamine was developed for the efficient and practical synthesis of quinazolines and quinazoline 3-oxides in good to excellent yields, respectively. The domino process involved an unprecedented isocyanide insertion into the N?H bond of ammonia or hydroxylamine and followed by condensation reaction at ambient conditions. (Figure presented.).
- Zhang, Lingjuan,Li, Juanjuan,Hu, Zhongyan,Dong, Jinhuan,Zhang, Xian-Ming,Xu, Xianxiu
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supporting information
p. 1938 - 1942
(2018/04/02)
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- TBHP as Methyl Source under Metal-Free Aerobic Conditions To Synthesize Quinazolin-4(3H)-ones and Quinazolines by Oxidative Amination of C(sp3)–H Bond
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tert-Butyl hydroperoxide (TBHP) served as the methyl source under metal-free aerobic conditions in the oxidative amination of the C(sp3)–H bond to synthesize quinazolin-4(3H)-ones and quinazolines from 2-aminobenzamides and 2-carbonyl-substituted anilines, respectively.
- Mukhopadhyay, Sushobhan,Barak, Dinesh S.,Batra, Sanjay
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p. 2784 - 2794
(2018/06/04)
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- One-pot three-component synthesis of quinazolines: Via a copper-catalysed oxidative amination reaction
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A copper-catalysed three-component reaction for constructing a series of quinazoline derivatives has been developed. In this system, solvents act as the reactants and different functional groups are well tolerated to obtain corresponding products in moderate to good yields.
- Duan, Tiantian,Zhai, Tianran,Liu, Huanhuan,Yan, Zilong,Zhao, Yue,Feng, Lei,Ma, Chen
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p. 6561 - 6567
(2016/07/16)
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- Asymmetric hydrogenation of quinazolinium salts catalysed by halide-bridged dinuclear iridium complexes bearing chiral diphosphine ligands
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Asymmetric hydrogenation of quinazolinium salts was catalysed by halogen-bridged dinuclear iridium complexes bearing chiral diphosphine ligands, yielding tetrahydroquinazoline and 3,4-dihydroquinazoline with high enantioselectivity. A derivative of chiral dihydroquinazoline was used as a chiral NHC ligand. This journal is
- Kita, Yusuke,Higashida, Kosuke,Yamaji, Kenta,Iimuro, Atsuhiro,Mashima, Kazushi
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supporting information
p. 4380 - 4382
(2015/03/18)
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- An Efficient Three-component, One-pot Synthesis of Quinazolines under Solvent-free and Catalyst-free Condition
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An efficient green protocol for the synthesis of quinazolines in the absence of solvent and catalyst has been developed. 2,4-Disubstituted quinazolines have been synthesized from three-component one-pot reactions of 2-aminoaryl ketones, orthoesters, and ammonium acetate. The present method has advantages of operational simplicity, substrate generality, clean reaction, high yields (76-94%), and moderate reaction time. The plausible mechanism of the reaction has been proposed based on the spectral characterization and single crystal X-ray analysis of isolated intermediate.
- Bhat, Subrahmanya Ishwar,Das,Trivedi, Darshak R.
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p. 1253 - 1259
(2015/08/06)
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- I2-catalyzed aerobic oxidative C(sp3)-H amination/C-N cleavage of tertiary amine: Synthesis of quinazolines and quinazolinones
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An iodine-catalyzed oxidative C(sp3)-H amination/C-N cleavage of tertiary amines couducted under an oxygen atmosphere has been developed and affords a route to quinazolines and quinazolinones in good to excellent yields via a domino ring annulation. The method is metal-free, peroxide-free, and operationally simple to implement with a wide scope of substrates and represents a new avenue for multiple C-N bond formations.
- Yan, Yizhe,Xu, Ying,Niu, Bin,Xie, Huifang,Liu, Yanqi
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p. 5581 - 5587
(2015/06/16)
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- Mechanistic study of a complementary reaction system that easily affords quinazoline and perimidine derivatives
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A new reaction between 2-aminobenzophenone and thiourea in dimethyl sulfoxide (DMSO) has been developed that primarily affords 4-phenylquinazoline as a single product. This reaction is also applicable, in general, to the reactions between thiourea and conformation-restricted β-amino ketones, such as 1-aminoanthracene-9,10-dione and 1-amino-9H-fluoren-9-one, to prepare perimidine derivatives. Experimental data is consistent with our computational study on the thermal decomposition of thiourea to form hydrogen sulfide and carbodiimide. This reaction involves a coupling between 2-aminobenzophenone and carbodiimide generated in situ from thiourea to form 4-phenylquinazolin-2(1H)-imine intermediate, and the generation of sulfur-containing reducing agent from hydrogen sulfide and DMSO, which reduces 4-phenylquinazolin-2(1H)-imine to 4-phenyl-1,2-dihydroquinazolin-2-amine. Elimination of ammonia from the latter yields 4-phenylquinazoline.
- Wang, Zerong Daniel,Eilander, Joshua,Yoshida, Motoko,Wang, Tianzhi
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p. 7664 - 7674
(2015/04/22)
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- Selective iodine-catalyzed intermolecular oxidative amination of C(sp 3)-H bonds with ortho-carbonyl-substituted anilines to give quinazolines
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Access to quinazolines: The selective amination of C(sp3)-H bonds adjacent to nitrogen or oxygen atoms of N-alkylamides, ethers, or alcohols with ortho-carbonyl-substituted anilines constitutes the first step in a tandem annulation that leads to quinazolines in good to excellent yields (see scheme; NIS=N-Iodosuccinimide, TBHP=tert-butyl hydroperoxide). The selectivity of the amination of primary and secondary C-H bonds is also noteworthy (left: >3:1, right: >99:1). Copyright
- Yan, Yizhe,Zhang, Yonghui,Feng, Chengtao,Zha, Zhenggen,Wang, Zhiyong
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supporting information; experimental part
p. 8077 - 8081
(2012/08/29)
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- Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity
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A novel metal-free intramolecular oxidative decarboxylative coupling of primary α-amino acids with 2-aminobenzoketones under mild and neutral conditions was developed. Different quinazolines can be selectively obtained by various oxidants.
- Yan, Yizhe,Wang, Zhiyong
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p. 9513 - 9515
(2011/10/01)
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- Ecofriendly and efficient one-pot procedure for the synthesis of quinazoline derivatives catalyzed by an acidic ionic liquid under aerobic oxidation conditions
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A three-component condensation reaction between 2-aminobenzophenone derivatives, formaldehyde or aromatic aldehydes, and ammonium acetate efficiently provides substituted quinazolines in a one-pot reaction in the presence of Bronsted acidic ionic liquid, 1-methylimidazolium triflouroacetate ([Hmim]TFA), in conjunction with aerobic oxidation. The ionic liquid was separated from the reaction mixture by simple extraction and was recycled three times without considerable loss in activity. Copyright Taylor & Francis Group, LLC.
- Dabiri, Minoo,Salehi, Peyman,Bahramnejad, Mahboobeh
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experimental part
p. 3214 - 3225
(2010/12/24)
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- Reactions of hydroxyglycines. New synthetic routes to 4-phenylquinazoline derivatives
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Reaction of hydroxyglycine with 2-aminobenzophenones gives 1,2-dihydro-4-phenyl-quinazoline-2-carboxylic acids in high yields and under mild conditions. These can be smoothly converted into the corresponding 3,4-dihydro isomers and into quinazoline derivatives via rearrangement and oxidation by air, respectively. The X-ray crystallographic structure of 6-chloro-1,2-dihydro-1-methyl-4-phenylquinazoline-2-carboxylic acid shows the carboxylate group at C(2) and the methyl group at N(1) to be in axial positions.
- Hoefnagel,Van Koningsveld,Van Meurs,Peters,Sinnema,Van Bekkum
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p. 6899 - 6912
(2007/10/02)
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- Antiarrhythmic active amidinohydrazones of substituted benzophenones. Part 5: Investigations on the stability of (Z)-2-amino-5-chlorobenzophenonamidinohydrazone acetate in solution
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The aqueous solution of the title compound can be used for injection for one year if it is stored at room temperature and under light protection. Under these conditions 8% of the E-isomer are produced. The reaction is reversible at day light. Red coloured products of decomposition are formed by long lasting influence of light. At higher temperatures or at sterilisation several products of decomposition are formed which structure is elucidated. For these decomposition a scheme is proposed.
- Schleuder,Richter,Keckeis,Jira
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