16107-83-8Relevant 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.).
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.
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.
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
Palladium-Catalyzed Three-Component Tandem Process: One-Pot Assembly of Quinazolines
Hu, Kun,Zhen, Qianqian,Gong, Julin,Cheng, Tianxing,Qi, Linjun,Shao, Yinlin,Chen, Jiuxi
supporting information, p. 3083 - 3087 (2018/05/28)
The first example of the palladium-catalyzed, three-component tandem reaction of 2-aminobenzonitriles, aldehydes, and arylboronic acids has been developed, providing a new approach for one-pot assembly of diverse quinazolines in moderate to good yields. A noteworthy feature of this method is the tolerance of bromo and iodo groups, which affords versatility for further synthetic manipulations. Preliminary mechanistic experiments indicate that this tandem process involves two possible mechanistic pathways for the formation of quinazolines via catalytic carbopalladation of the cyano group.
Ru(II)-Catalyzed C-H Activation and Annulation Reaction via Carbon-Carbon Triple Bond Cleavage
Prakash, Rashmi,Bora, Bidisha R.,Boruah, Romesh C.,Gogoi, Sanjib
, p. 2297 - 2300 (2018/04/30)
An unprecedented Ru(II)-catalyzed C-H activation and annulation reaction, which proceeds via C-C triple bond cleavage, is reported. This reaction of 2-phenyldihydrophthalazinediones with alkynes, which works most efficiently in the presence of bidented ligand 1,3-bis(diphenylphosphino)propane, affords good yields of substituted quinazolines.
Metal-Free One-Pot Synthesis of (Tetrahydro)Quinolines through Three-Component Assembly of Arenediazonium Salts, Nitriles, and Styrenes
Youn, So Won,Yoo, Huen Ji,Lee, Eun Mi,Lee, Seo Young
supporting information, p. 278 - 283 (2017/12/26)
A highly efficient and convenient metal-free, one-pot synthesis of diversely substituted (tetrahydro)quinolines has been achieved through a three-component assembly reaction of arenediazonium salts, nitriles, and styrenes. In sharp contrast to the prior works with the same reagent blend, the formation of N-arylnitrilium intermediates from arenediazonium salts and nitriles was followed by reaction with styrenes, leading to 3,4-dihydroquinolinium salts as a common intermediate. These could be further transformed to quinolines and tetrahydroquinolines depending on the reaction conditions. The advantages of this protocol include its simplicity, metal-free and mild conditions, readily available starting materials, and good functional group tolerance. (Figure presented.).
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.
Transition Metal-Free Visible Light-Driven Photoredox Oxidative Annulation of Arylamidines
Shen, Zi-Chao,Yang, Pan,Tang, Yu
, p. 309 - 317 (2016/01/15)
A fast catalytic synthesis of multisubstituted quinazolines from readily available amidines via visible light-mediated oxidative C(sp3)-C(sp2) bond formation has been established. This reaction is a metal-free oxidative coupling catalyzed by a photoredox organocatalyst. The protocol features low catalyst loading (1 mol %).
Efficient synthesis of 2-arylquinazolines via copper-catalyzed dual oxidative benzylic C-H aminations of methylarenes
Liu, Li-Yan,Yan, Yi-Zhe,Bao, Ya-Jie,Wang, Zhi-Yong
, p. 1216 - 1220 (2015/12/30)
A novel copper-catalyzed dual oxidative benzylic C-H aminations of methylarenes with 2-aminobenzoketones in the presence of ammonium acetate was developed. This reaction represents a new avenue for 2-arylquinazolines with good yields. A key intermediate was detected and the kinetics isotope effect (KIE) indicated that C-H bond cleavage was the rate-determining step.
