106910-91-2Relevant academic research and scientific papers
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.).
Four-component quinazoline synthesis from simple anilines, aromatic aldehydes and ammonium iodide under metal-free conditions
Chen, Jinjin,Chang, Dan,Xiao, Fuhong,Deng, Guo-Jun
supporting information, p. 5459 - 5463 (2019/01/03)
A four-component procedure for the preparation of substituted quinazolines from anilines, aromatic aldehydes and ammonium iodide is described. The C-H bond ortho to the amino group in anilines was directly functionalized under metal-free conditions. Two a
Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines
Cheung, Wing,Patch, Raymond J.,Player, Mark R.
supporting information, 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.
Synthesis of Quinazolines from N,N′-Disubstituted Amidines via I2/KI-Mediated Oxidative C-C Bond Formation
Lv, Zhigang,Wang, Bingnan,Hu, Zhiyuan,Zhou, Yiming,Yu, Wenquan,Chang, Junbiao
, p. 9924 - 9930 (2016/11/02)
An I2/KI-promoted oxidative C-C bond formation reaction from C(sp3)-H and C(sp2)-H bonds has been used to construct quinazoline skeletons from N,N′-disubstituted amidines. The required substrates are readily prepared from the corresponding acyl chlorides, anilines, and alkyl/benzylamines by sequential amidation, chlorination, and amination reactions. Under the optimal oxidative cyclization conditions, all these amidines were conveniently transformed into the expected products in moderate to good yields. This practical and environmentally benign approach works well with crude amidine intermediates and can also be carried out on a gram scale.
Synthesis of quinazolines via CuO nanoparticles catalyzed aerobic oxidative coupling of aromatic alcohols and amidines
Zhang, Wu,Guo, Fei,Wang, Fei,Zhao, Na,Liu, Liang,Li, Jia,Wang, Zhenghua
, p. 5752 - 5756 (2014/07/22)
CuO nanoparticles were found to be efficient catalysts for the synthesis of quinazoline derivatives; twenty-four products were obtained with good to excellent yields via reaction of N-arylamidines and aromatic aldehydes or benzyl alcohol in air. Neither a
One-pot synthesis of quinazoline derivatives via [2+2+2] cascade annulation of diaryliodonium salts and two nitriles
Su, Xiang,Chen, Chao,Wang, Yong,Chen, Junjie,Lou, Zhenbang,Li, Ming
supporting information, p. 6752 - 6754 (2013/07/26)
An efficient one-pot approach to multiple substituted quinazolines with diaryliodonium salt 1, and two nitriles 2 has been presented. The reaction enables great flexibility of the substitution patterns on quinazolines and is applicable to two different nitriles to give a regio-selective product.
Rearrangement Reactions of 1,3,6-Triaryl-1,4-dihydro-s-tetrazines leading to 2,4-Diarylquinazolines, 1-Anilino-3,5-diaryl-1H-1,2,4-triazoles, 1,3,5-Triaryl-1H-1,2,4-triazoles, and 2,5-Diaryl-1H-1,3,4-oxadiazoles. X-ray Structure Determination of 6-Isopropyl-2,4-diphenylquinazoline
Hunter, Daniel,Neilson, Douglas G.,Weakley, Timothy J.R.
, p. 2709 - 2712 (2007/10/02)
1,3,6-Triaryl-1,4-dihydro-s-tetrazines (2c-g) rearrange on heating at ca. 200 deg C to 2,4-diarylquinazolines (for which an X-ray determination was carried out on the 6-isopropyl compound) and 1-anilino-3,5-diaryl-1H-1,2,4-triazoles as major products.Hydrolysis in chloroform solution of the title compounds (2) and their 1-alkyl analogues gives rise to 1-aryl (or alkyl)-3,5-diaryl-1H-1,2,4-triazoles and 2,5-diaryl-1,3,4-oxadiazoles.
