1399327-91-3Relevant academic research and scientific papers
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.
Copper-catalyzed domino reaction between 1-(2-halophenyl)methanamines and amidines or imidates for the synthesis of 2-substituted quinazolines
Omar, Mohamed A.,Conrad, Jürgen,Beifuss, Uwe
, p. 3061 - 3072 (2014/04/17)
The CuI-catalyzed domino reaction between 1-(2-bromophenyl)methanamines and amidines using K3PO4 as the base, pivalic acid as the additive, and aerial oxygen as the oxidant gives access to substituted quinazolines in a single step wi
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
Copper-catalyzed annulation of amidines for quinazoline synthesis
Lv, Yunhe,Li, Yan,Xiong, Tao,Pu, Weiya,Zhang, Hongwei,Sun, Kai,Liu, Qun,Zhang, Qian
, p. 6439 - 6441 (2013/08/23)
An efficient Cu-catalyzed synthesis of quinazolines via the C-N bond formation reactions between N-H bonds of amidines and C(sp3)-H bonds adjacent to sulfur or nitrogen atoms in the commonly used solvents, such as DMSO, DMF, DMA, NMP or TMEDA,
Copper-catalyzed synthesis of quinazolines in water starting from o-bromobenzylbromides and benzamidines
Malakar, Chandi C.,Baskakova, Alevtina,Conrad, Jürgen,Beifuss, Uwe
supporting information; experimental part, p. 8882 - 8885 (2012/09/22)
Water makes it possible: The Cu2O-catalyzed reaction between easily available o-bromobenzylbromides and benzamidines by using Cs 2CO3 as the base and N,N'-dimethylethylenediamine (DMEDA) as the additive in water as the solvent gives access to substituted quinazolines in a single step with yields ranging from 57 to 85 % (see scheme).
