1399327-76-4Relevant academic research and scientific papers
Palladium-catalyzed carbonylative synthesis of quinazolines: Silane act as better nucleophile than amidine
Lu, Jia-Ming,Huo, Yong-Wang,Qi, Xinxin,Wu, Xiao-Feng
, (2021/05/31)
A palladium-catalyzed reductive carbonylation reaction has been developed for the synthesis of quinazolines. With N-(2-iodophenyl)benzimidamide as starting materials, a series of quinazolines were obtained through the aromatic aldehyde intermediates in moderate to good yields with good functional group compatibilities. In this system, silane act as better nucleophile than amidine.
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.
Assembly of 4H-chromenes, imidazobenzothiazines and quinazolines via copper-catalyzed domino reactions using 2-halobenzyl tosylates as substrates
Omar, Mohamed A.,Conrad, Jürgen,Beifuss, Uwe
, p. 5682 - 5695 (2015/03/30)
The use of 2-halobenzyl tosylates as substrates in copper-catalyzed domino intermolecular substitution/intramolecular arylation processes for the efficient and selective preparation of heterocycles is reported for the first time. Reaction of 2-halobenzyl tosylates with β-ketoesters delivers 4H-chromenes with yields ranging between 59 and 89%. Imidazobenzothiazines are formed with yields up to 82% upon reaction of 2-halobenzyl tosylates with 2-mercaptoimidazoles. When 2-halobenzyl tosylates are reacted with benzamidines the corresponding quinazolines are obtained.
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
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).
