34637-66-6Relevant academic research and scientific papers
Access to 2-arylquinazolinesviacatabolism/reconstruction of amino acids with the insertion of dimethyl sulfoxide
Ma, Jin-Tian,Wang, Li-Sheng,Chai, Zhi,Chen, Xin-Feng,Tang, Bo-Cheng,Chen, Xiang-Long,He, Cai,Wu, Yan-Dong,Wu, An-Xin
supporting information, p. 5414 - 5417 (2021/06/09)
Quinazoline skeletons are synthesized by amino acid catabolism/reconstruction combined with the insertion/cyclization of dimethyl sulfoxide for the first time. The amino acid acts as a carbon and nitrogen source through HI-mediated catabolism and is then reconstructed using aromatic amines and dimethyl sulfoxide (DMSO) as a one-carbon synthon. This protocol is of great significance for the further study of the conversion of amino acids.
Niacin as a Potent Organocatalyst towards the Synthesis of Quinazolines Using Nitriles as C–N Source
Gujjarappa, Raghuram,Vodnala, Nagaraju,Reddy, Velma Ganga,Malakar, Chandi C.
, p. 803 - 814 (2020/02/18)
An efficient and cost-effective Vitamin-B3-catalyzed protocol towards the synthesis of diversely substituted quinazolines is illustrated using 2-aminobenzylamines and nitriles as substrates. An organocatalytic transformation has been investigat
Divergent Synthesis of Quinazolines Using Organocatalytic Domino Strategies under Aerobic Conditions
Gujjarappa, Raghuram,Maity, Suvik K.,Hazra, Chinmoy K.,Vodnala, Nagaraju,Dhiman, Shiv,Kumar, Anil,Beifuss, Uwe,Malakar, Chandi C.
, p. 4628 - 4638 (2018/09/13)
An easy and efficient organocatalytic approach to the synthesis of 2-substituted quinazolines is described based on the reaction between 2-aminobenzylamines and aldehydes or alcohols or amines. Three organocatalytic platforms were investigated, using 3-nitropyridine, pyridine N-oxide, and vitamin B3. Having established the new catalytic systems, the tandem transformations of 2-aminobenzylamines to give substituted quinazolines were achieved in excellent yields and with a broad substrate scope, with no formation of toxic side-products. The investigated conditions are not restricted to the use of aldehydes; the protocol also works well with alcohols or amines as substrates. These are oxidized in situ to the corresponding aldehydes to achieve the successful transformation. A mechanistic proposal has been drawn up based on control experiments. We found that under aerobic conditions, catalytic amounts of H2O2 can be generated; this plays a key role in the efficacy of the described approach. The green chemistry metrics of the developed method are also presented. The E factor of 8.18 mg/1 mg demonstrates that the reported method is an excellent complement to previous protocols.
Base-Promoted Synthesis of 2-Aryl Quinazolines from 2-Aminobenzylamines in Water
Chatterjee, Tanmay,Kim, Dong In,Cho, Eun Jin
, p. 7423 - 7430 (2018/07/29)
A transition-metal-free procedure for the synthesis of a highly valuable class of heteroaromatics, quinazolines, was developed by using easily available 2-aminobenzylamines and α,α,α-trihalotoluenes. The transformation proceeded smoothly in the presence of only sodium hydroxide and molecular oxygen in water at 100 °C, furnishing a variety of 2-aryl quinazolines. The crystallization process of the crude reaction mixture for the purification of the solid products circumvents huge solvent-consuming workup and column chromatographic techniques, which make the overall process more sustainable and economical.
ABNO-Catalyzed Aerobic Oxidative Synthesis of 2-Substituted 4H-3,1-Benzoxazines and Quinazolines
Ma, Jiaqi,Wan, Yan,Hong, Chao,Li, Meichao,Hu, Xinquan,Mo, Weimin,Hu, Baoxiang,Sun, Nan,Jin, Liqun,Shen, Zhenlu
, p. 3335 - 3342 (2017/06/29)
A new transition-metal-free 9-azabicyclo[3.3.1]nonan-N-oxyl (ABNO) catalyzed aerobic oxidative synthesis of 2-substituted 4H-3,1-benzoxazines and quinazolines has been developed through cascade reaction of aldehydes with 2-aminobenzyl alcohols and 2-amino
A quinazoline compound of the catalytic oxidation synthesis method (by machine translation)
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Paragraph 0050; 0051; 0052, (2017/08/30)
The invention discloses a quinazoline compound of the catalytic oxidation synthesis method, the method is: in order to 2 - amido amine compounds and aqueous reaction substrate and the two feeding molar ratio of 100:100 - 120, in order to 9 - azabicyclo [3
Lewis acid-catalyzed 2-arylquinazoline formation from: N ′-arylbenzimidamides and paraformaldehyde
Cheng, Xiufang,Wang, Huamin,Xiao, Fuhong,Deng, Guo-Jun
supporting information, p. 5773 - 5776 (2016/11/06)
An efficient procedure for the synthesis of 2-arylquinazolines from N′-arylbenzimidamides has been developed under transition-metal-free conditions. In this process, stable and low-toxicity paraformaldehyde was used as the carbon source. A broad range of
Copper-Catalyzed Multicomponent Domino Reaction of 2-Bromoaldehydes, Benzylamines, and Sodium Azide for the Assembly of Quinazoline Derivatives
Xu, Cheng,Jia, Feng-Cheng,Zhou, Zhi-Wen,Zheng, Si-Jie,Li, Han,Wu, An-Xin
supporting information, p. 3000 - 3006 (2016/04/26)
An efficient three-component domino reaction of 2-bromoaldehydes, benzylamines, and sodium azide has been developed for the synthesis of quinazoline derivatives. This domino process involves copper-catalyzed SNAr, oxidation/cyclization, and denitrogenation sequences. The mild catalytic system enabled the effective construction of three C-N bonds in one operation.
Palladium-catalyzed one pot 2-arylquinazoline formation via hydrogen-transfer strategy
Wang, Huamin,Chen, Hui,Chen, Ya,Deng, Guo-Jun
, p. 7792 - 7799 (2014/12/10)
The palladium catalytic system was first applied to 2-arylquinazoline synthesis via hydrogen transfer methodology. Various (E)-2-nitrobenzaldehyde O-methyl oximes reacted easily with alcohols or benzyl amines to provide N-heterocyclic compounds in good to
Synthesis of quinazolines and tetrahydroquinazolines: Copper-catalyzed tandem reactions of 2-bromobenzyl bromides with aldehydes and aqueous ammonia or amines
Fan, Xuesen,Li, Bin,Guo, Shenghai,Wang, Yuanyuan,Zhang, Xinying
supporting information, p. 739 - 743 (2014/03/21)
An efficient synthesis of diversely substituted quinazolines and 1,2,3,4-tetrahydroquinazolines through copper-catalyzed tandem reactions of the readily available 2-bromobenzyl bromides, aldehydes, and aqueous ammonia or amines has been developed. By using ammonia and simple aliphatic amines as the nitrogen source, the present method provides a versatile and practical protocol for the synthesis of quinazolines and 1,2,3,4-tetrahydroquinazolines. Copper on the beat: An efficient, simple and economical synthesis of diversely substituted quinazolines and 1,2,3,4-tetrahydroquinazolines has been developed through copper-catalyzed tandem reactions of the readily available 2-bromobenzyl bromides, aldehydes, and aqueous ammonia or simple aliphatic amines. Copyright
