92151-67-2Relevant 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.
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
A convenient one-pot procedure for the synthesis of 2-aryl quinazolines using active MnO2 as oxidant
Peng, Yi-Yuan,Zeng, Yuyun,Qiu, Ganyinsheng,Cai, Lisheng,Pike, Victor W.
experimental part, p. 1240 - 1245 (2010/11/18)
(Chemical Equation Presented) A variety of 2-aryl quinazolines were synthesized from the condensation of 2-aminobenzylamines and aryl aldehydes to form 2-aryl-1,2,3,4-tetrahydroquinazolines and subsequent oxidation of the intermediates with MnO2/sub
