1806-66-2Relevant academic research and scientific papers
Mn(iii)-mediated cascade cyclization of 1-(azidomethyl)-2-isocyanoarenes with organoboronic acids: Construction of quinazoline derivatives
Kumar, Gujjenahalli Ramalingaiah Yogesh,Begum, Noor Shahina
, p. 9811 - 9817 (2021/06/15)
A novel and efficient Mn(iii)-mediated oxidative radical cascade reaction of 1-(azidomethyl)-2-isocyanoarenes with organoboronic acids is reported. The single electron oxidation of a commercially available organo boronic acid in the presence of a mild oxidant, Mn(OAc)3·2H2O, resulted in moderate yields of the corresponding quinazoline derivatives.
Vinylene carbonate: Beyond the ethyne surrogate in rhodium-catalyzed annulation with amidines toward 4-methylquinazolines
Wang, Chang,Fan, Xiaodong,Chen, Fan,Qian, Peng-Cheng,Cheng, Jiang
supporting information, p. 3929 - 3932 (2021/04/26)
In this paper, we developed a rhodium-catalyzed annulation of vinylene carbonate with amidines, leading to 4-methylquinazolines with moderate to excellent yields. This procedure proceeded by sequentialortho-acylation and annulation, where vinylene carbonate served as the acetylation reagent rather than the ethyne surrogate.
Efficient synthesis of quinazolines by the iron-catalyzed acceptorless dehydrogenative coupling of (2-aminophenyl)methanols and benzamides
Zhang, Shi-Qi,Cui, Yao,Guo, Bin,Young, David J.,Xu, Ze,Li, Hong-Xi
, (2020/12/13)
The acceptorless dehydrogenation coupling (ADC) of (2-aminophenyl)methanols with benzamides was achieved with catalytic FeCl2·4H2O in an efficient synthesis of quinazolines. This simple catalytic system is atom-economical, environmentally benign and suited to a variety of substrates.
Hydrogen peroxide-mediated synthesis of 2,4-substituted quinazolines: Via one-pot three-component reactions under metal-free conditions
Nguyen, Khang X.,Nguyen, Tung T.,Pham, Phuc H.,Phan, Anh N. Q.,Phan, Nam T. S.,Trinh, Khang H.
, p. 29900 - 29909 (2020/10/06)
An efficient metal-free synthesis of 2,4-substituted quinazolines via a hydrogen peroxide-mediated one-pot three-component reaction of 2-aminoaryl ketones, aldehydes, and ammonium acetate has been developed. The transformation proceeded readily under mild conditions in the presence of commercially available hydrogen peroxide. The significant advantages of this approach are (1) the readily available atom-efficient and green hydrogen peroxide as oxidant; (2) no transition metal catalyst is required; (3) mild reaction conditions; and (4) wide substrate scope. To the best of our knowledge, utilizing hydrogen peroxide as an atom-efficient and green oxidant for the synthesis of 2,4-substituted quinazolines has not previously been reported in the literature. This method is complementary to previous protocols for the synthesis of 2,4-substituted quinazolines. This journal is
Sulfur-Mediated Decarboxylative Coupling of 2-Nitrobenzyl Alcohols and Arylacetic Acids
Le, Ha V.,Nguyen, Duyen K.,Nguyen, Khang X.,Nguyen, Tung T.,Pham, Phuc H.,Phan, Nam T. S.
supporting information, p. 1112 - 1116 (2020/07/04)
We report a new method for the synthesis of substituted quinazolines by the condensation of 2-nitrobenzyl alcohols with arylacetic acids. The transformation requires the use of urea as a nitrogen source, elemental sulfur as a promoter, DABCO as a base, and DMSO as a solvent. Functionalities such as chloro, fluoro, trifluoromethyl, thienyl, and indolyl groups were all compatible with the reaction conditions. Because our method uses stable simple substrates to obtain the N,N-heterocycles in the absence of transition metals, it offers a potential pathway for preparing complex structures under mild conditions.
Visible-Light-Induced Benzylic C-H Functionalization for the Synthesis of 2-Arylquinazolines
Zhang, Jingchang,Wang, Qibao,Guo, Yongen,Ding, Lin,Yan, Maocai,Gu, Yinglin,Shi, Jiajia
supporting information, p. 5934 - 5936 (2019/10/14)
This work reports a mild and efficient approach for the synthesis of substituted quinazolines using 1-(2-aminoaryl)ethan-1-ones in conjunction with arylmethanamines as starting materials via visible-light-induced benzylic C–H functionalization. The reaction proceeded at room temperature with low catalyst loading and the reaction system was clean from beginning to end. Significantly, this method exhibited good tolerance even to free hydroxyl group and amino group contained in substrates.
Synthesis of Quinazoline and Quinazolinone Derivatives via Ligand-Promoted Ruthenium-Catalyzed Dehydrogenative and Deaminative Coupling Reaction of 2-Aminophenyl Ketones and 2-Aminobenzamides with Amines
Kirinde Arachchige, Pandula T.,Yi, Chae S.
supporting information, (2019/05/08)
The in situ formed ruthenium catalytic system ([Ru]/L) was found to be highly selective for the dehydrogenative coupling reaction of 2-aminophenyl ketones with amines to form quinazoline products. The deaminative coupling reaction of 2-aminobenzamides with amines led to the efficient formation of quinazolinone products. The catalytic coupling method provides an efficient synthesis of quinazoline and quinazolinone derivatives without using any reactive reagents or forming any toxic byproducts.
Maximizing the Catalytic Activity of Nanoparticles through Monolayer Assembly on Nitrogen-Doped Graphene
Yu, Chao,Guo, Xuefeng,Shen, Mengqi,Shen, Bo,Muzzio, Michelle,Yin, Zhouyang,Li, Qing,Xi, Zheng,Li, Junrui,Seto, Christopher T.,Sun, Shouheng
supporting information, p. 451 - 455 (2018/02/21)
We report a facile method for assembly of a monolayer array of nitrogen-doped graphene (NG) and nanoparticles (NPs) and the subsequent transfer of two layers onto a solid substrate (S). Using 3 nm NiPd NPs as an example, we demonstrate that NiPd-NG-Si (Si=silicon wafer) can function as a catalyst and show maximum NiPd catalysis for the hydrolysis of ammonia borane (H3NBH3, AB) with a turnover frequency (TOF) of 4896.8 h?1 and an activation energy (Ea) of 18.8 kJ mol?1. The NiPd-NG-S catalyst is also highly active for catalyzing the transfer hydrogenation from AB to nitro compounds, leading to the green synthesis of quinazolines in water. Our assembly method can be extended to other graphene and NP catalyst materials, providing a new 2D NP catalyst platform for catalyzing multiple reactions in one pot with maximum efficiency.
Accessing Polysubstituted Quinazolines via Nickel Catalyzed Acceptorless Dehydrogenative Coupling
Parua, Seuli,Sikari, Rina,Sinha, Suman,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
, p. 11154 - 11166 (2018/09/06)
Two environmentally benign methods for the synthesis of quinazolines via acceptorless dehydrogenative coupling of 2-aminobenzylamine with benzyl alcohol (Path A) and 2-aminobenzylalcohol with benzonitrile (Path B), catalyzed by cheap, earth abundant and easy to prepare nickel catalysts, containing tetraaza macrocyclic ligands (tetramethyltetraaza[14]annulene (MeTAA) or 6,15-dimethyl-8,17-diphenyltetraaza[14]annulene (MePhTAA)) are reported. A wide variety of substituted quinazolines were synthesized in moderate to high yields starting from cheap and easily available starting precursors. A few control reactions were performed to understand the mechanism and to establish the acceptorless dehydrogenative nature of the catalytic reactions.
Lewis-Acid-Catalysed Activation of Nitriles: A Microwave-Assisted Solvent-Free Synthesis of 2,4-Disubstituted Quinazolines and 1,3-Diazaspiro[5.5]undec-1-enes
Saikia, Ujwal Pratim,Borah, Geetika,Pahari, Pallab
supporting information, p. 1211 - 1217 (2018/03/21)
Two different modes of cyclization take place to synthesize quinazoline, quinazolinone, and 1,3-diazaspiro[5.5]undec-1-ene derivatives through the Lewis-acid-catalysed activation of both aliphatic and aromatic nitriles in a single-step, solvent-free, and transition-metal-free reaction. An amidine is expected to form as an intermediate; this then undergoes intramolecular cyclization in a one-pot reaction sequence. The reaction is carried out under microwave irradiation using trimethylsilyltrifluoromethane sulfonate (TMSOTf) as a catalyst and nitriles as a nitrogen source with the respective reaction partners.
