1399327-71-9Relevant articles and documents
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.