1229610-02-9Relevant academic research and scientific papers
DDQ/TBHP-induced oxidative cyclization process: A metal-free approach for the synthesis of 2-phenylquinazolines
Rachakonda, Sridhar,Pratap, P.Surya,Basaveswara Rao, Mandava V.
, p. 2065 - 2069 (2012)
Various 2-phenylquinazoline derivatives were synthesized under metal-free conditions from readily available 2-aminophenyl ketones and benzylamines via condensation and oxidative cyclization using 2,3-dichloro-5,6-dicyano-1,4- benzoquinone (DDQ) as a versatile reagent. The reaction gave the corresponding 2-phenylquinazoline derivatives in good to excellent yields (up to 92%). Georg Thieme Verlag Stuttgart ? New York.
Synthesis of quinazolines over recyclable Fe3O4@SiO2-PrNH2-Fe3+ nanoparticles: A green, efficient, and solvent-free protocol
Eidi, Esmaiel,Kassaee, Mohamad Z.,Nasresfahani, Zahra,Cummings, Peter T.
, (2018)
A practical and efficient method is developed for efficient synthesis of quinazoline derivatives through condensation reaction of 2-aminoaryl ketone, an aldehyde, and ammonium acetate, over magnetic Fe3O4@SiO2-PrNH2/
Copper-Catalyzed Three-Component Cascade Reaction of Benzaldehyde with Benzylamine and Hydroxylamine or Aniline: Synthesis of 1,2,4-Oxadiazoles and Quinazolines
Wang, Chao,Rui, Xiyan,Si, Dongjuan,Dai, Rupeng,Zhu, Yueyue,Wen, Hongmei,Li, Wei,Liu, Jian
supporting information, p. 2825 - 2833 (2021/04/26)
The analogous three-component synthesis strategy for substituted 1,2,4-oxadiazole and quinazoline derivatives from readily available benzaldehyde, benzylamine and hydroxylamine or aniline has been developed. Both the cascade reaction sequences involves nucleophilic addition of C?N bond, introduction a halogen donor, nucleophilic substitution and Cu(II)-catalyzed aerobic oxidation. This synthesis methodology demonstrated good yields, broad substrate scope and oxygen as a green oxidant. Thus, this synthesis protocol provides strategies for the construction of substituted 1,2,4-oxadiazole and quinazolines from readily and simple starting materials. (Figure presented.).
TMSOTf-catalyzed synthesis of substituted quinazolines using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions
Chan, Chieh-Kai,Lai, Chien-Yu,Wang, Cheng-Chung
, p. 7201 - 7212 (2020/10/02)
In this article, we report an efficient and mild synthetic route for the construction of substituted quinazolines from functionalized 2-aminobenzophenones with various benzaldehydes usingcat. TMSOTf and hexamethyldisilazane (HMDS) under neat, metal-free and microwave irradiation conditions in which gaseous ammonia was formedin situ. This synthetic protocol provided the desired quinazolines with a broad substrate scope in good to excellent yields. Some structures were confirmed by X-ray single-crystal diffraction analysis.
Pd-Catalyzed tandem reaction of N-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines
Zhu, Jianghe,Shao, Yinlin,Hu, Kun,Qi, Linjun,Cheng, Tianxing,Chen, Jiuxi
, p. 8596 - 8603 (2018/11/27)
The synthesis of 2,4-disubstituted quinazolines by a palladium-catalyzed reaction of arylboronic acids with N-(2-cyanoaryl)benzamides has been developed with moderate to excellent yields. The method shows good functional group tolerance. In particular, ha
Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines
Cheung, Wing,Patch, Raymond J.,Player, Mark R.
, p. 2368 - 2371 (2018/05/25)
A single-pot procedure for the synthesis of 2,4-diarylquinazolines is described which involves a silver oxide-mediated C–H activation/C–N bond formation process. The generality of this method with respect to substituent effects is presented along with studies leading to process optimization. Mechanistic investigations provide support for the involvement of radical intermediates in the reaction process.
Copper-Catalyzed Synthesis of Substituted Quinazolines from Benzonitriles and 2-Ethynylanilines via Carbon-Carbon Bond Cleavage Using Molecular Oxygen
Wang, Xu,He, Dandan,Huang, Yubing,Fan, Qihang,Wu, Wanqing,Jiang, Huanfeng
, p. 5458 - 5466 (2018/05/28)
A copper-catalyzed process for the synthesis of substituted quinazolines from benzonitriles and 2-ethynylanilines using molecular oxygen (O2) as sole oxidant is described. The mild catalytic system enabled the effective cleavage of the C-C triple bond and construction of new C-N and C-C bonds in one operation. Furthermore, the compound N,N-dimethyl-4-(2-(4-(trifluoromethyl)phenyl)quinazolin-4-yl)aniline (3dj) exhibited obvious aggregation-induced emission phenomenon, and the fluorescence quantum yield (ΦF,film) and lifetime (τfilm) were measured to be 45.5% and 5.8 ns in thin films state, respectively.
Synthesis of Quinazolines via an Iron-Catalyzed Oxidative Amination of N-H Ketimines
Chen, Cheng-Yi,He, Fengxian,Tang, Guangrong,Yuan, Huiqing,Li, Ning,Wang, Jinmin,Faessler, Roger
, p. 2395 - 2401 (2018/02/23)
An efficient synthesis of quinazolines based on an iron-catalyzed C(sp3)-H oxidation and intramolecular C-N bond formation using tert-BuOOH as the terminal oxidant is described. The reaction of readily available 2-alkylamino benzonitriles with various organometallic reagents led to 2-alkylamino N-H ketimine species. The FeCl2-catalyzed C(sp3)-H oxidation of the alkyl group employing tert-BuOOH followed by intramolecular C-N bond formation and aromatization afforded a wide variety of 2,4-disubstituted quinazolines in good to excellent yields.
Palladium-Catalyzed Cross-Coupling of 4-Tosyloxyquinazolines with Organoindium Reagents: An Efficient Route to 4-Substituted Quinazolines
Ye, Xinglin,Yuan, Jianjun,Zhou, Yirong,Deng, Zhihong,Mao, Xuechun,Peng, Yiyuan
, p. 3976 - 3984 (2016/11/11)
An efficient route to 4-substituted quinazolines by arylation or alkylation of quinazolinones under mild conditions is described. 4-Tosyloxyquinazolines were obtained through the reaction of quinazolinones and p-methylbenzenesulfonyl chloride in the presence of K2CO3. The cross-coupling reaction of 4-tosyloxyquinazolines with organoindium reagents, carried out in tetrahydrofuran, catalyzed by Pd2(dba)3/ (2-furyl)3P led to the formation of 4-functionalized quinazolines in good to excellent yields. Higher yields were obtained by the one-pot reaction of quinazolinone, p-methylbenzenesulfonyl chloride, Pd2(dba)3-/(2-furyl)3P, and organoindium reagent. These methods using organoindium compounds as coupling partners provided an efficient route to 4-(hetero)aryl/alkylquinazolines, especially 4-substituted quinazolines bearing a halogen scaffold.
Nickel-catalyzed Kumada Cross-coupling Reaction for the Synthesis of 2,4-Diarylquinazolines
Ye, Xinglin,Yuan, Zhihan,Zhou, Yirong,Yang, Qin,Xie, Yepeng,Deng, Zhihong,Peng, Yiyuan
supporting information, p. 1956 - 1962 (2016/11/24)
A series of 2,4-diarylquinazolines have been successfully synthesized via the Ni-catalyzed cross-coupling reaction of quinazoline-4-tosylates and aryl Grignard reagents, which provided alternative straightforward approaches for the introduction of aryl groups to quinazolines at C-4 position.
