- Preparation of 4-arylquinazolines with: O-(N-alkyl, N-p-tosyl)aminobenzonitriles, aryllithiums, and NIS
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The treatment of o-(N-alkyl,N-p-tosyl)aminobenzonitriles with aryllithiums, followed by the reaction with water, NIS under irradiation with a fluorescent lamp, and then tBuOK gave 2-alkyl-4-arylquinazolines or 4-arylquinazolines in good to moderate yields. The present reaction proceeds through the formation of N-iodoimines from imines with NIS, the generation of iminyl radicals, the 1,6-H shift by iminyl radicals, the cyclization via 6-exo-tet mode, and finally the elimination of p-toluenesulfinate to generate 2-alkyl-4-arylquinazolines or 4-arylquinazolines.
- Naruto, Hiroki,Togo, Hideo
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p. 5666 - 5676
(2020/08/21)
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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 0074-0077
(2019/09/17)
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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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- 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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supporting information
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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