Copper-Catalyzed Tandem Reaction of 2-Aminobenzamides with Tertiary Amines for the Synthesis of Quinazolinone Derivatives

Xü, Wei; Zhu, Xiao-Rui; Qian, Peng‐Cheng; Zhang, Xing‐Guo; Deng, Chen‐Liang

doi:10.1055/s-0036-1588881

Cited by 12 publications

(1 citation statement)

References 6 publications

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“…91% (26.8 mg) using 6a , 2a , and b for 3 h; a white solid (EtOAc: n -Hexane = 1:4), mp 118–120 °C; 1 H NMR (CDCl 3 , 400 MHz) δ 8.26 (dd, J = 7.8, 1.0 Hz, 1H), 7.75 (td, J = 7.6, 1.2 Hz, 1H), 7.70 (d, J = 7.6 Hz, 1H), 7.55 (t, J = 7.2 Hz, 2H), 7.50 (t, J = 7.2 Hz, 1H), 7.45 (td, J = 7.5, 1.0 Hz, 1H), 7.25 (d, J = 8.4 Hz, 2H), 2.39 (t, J = 7.8 Hz, 2H), 1.72 (sextet, J = 7.5 Hz, 2H), 0.86 (t, J = 7.4 Hz, 3H); 13 C{ 1 H} NMR (CDCl 3 , 100 MHz) δ 162.4, 156.8, 147.5, 137.3, 134.4, 129.7, 129.1, 128.3, 127.0, 126.9, 126.4, 120.7, 37.6, 20.4, 13.7; EIMS m / z 264 (M + ), 249, 235, 221, 160, 119, 77. Spectral data of 7g were consistent with data reported in the literature …”

Section: Methodsmentioning

confidence: 99%

One-Pot Three-Component Reaction for the Synthesis of 3,4-Dihydroquinazolines and Quinazolin-4(3H)-ones

Chen,

Ji,

Choi

et al. 2024

J. Org. Chem.

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A highly efficient and straightforward one-pot synthesis of diversely substituted 3,4-dihydroquinazolines and quinazolin-4(3H)-ones has been achieved through a domino three-component assembly reaction of arenediazonium salts, nitriles, and bifunctional aniline derivatives. This new protocol involves three C−N bond formations through the initial formation of N-arylnitrilium intermediates from arenediazonium salts and nitriles, followed by the sequential nucleophilic addition and cyclization reactions with bifunctional anilines, leading to such Nheterocyclic compounds of biological and pharmacological importance. This method offers a simple, expedient, and robust approach with the use of amenable and easily accessible reactants/ reagents under metal-free mild conditions, good functional group tolerance, and high efficiency. The synthetic applications were also demonstrated by derivatization of the products obtained from these processes and syntheses of a diverse range of valuable polycyclic N-heterocycles.

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Section: Methodsmentioning

confidence: 99%

One-Pot Three-Component Reaction for the Synthesis of 3,4-Dihydroquinazolines and Quinazolin-4(3H)-ones

Chen,

Ji,

Choi

et al. 2024

J. Org. Chem.

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Sulfur‐Promoted Synthesis of 2‐Aroylquinazolin‐4(3H)‐ones by Oxidative Condensation of Anthranilamide and Acetophenones

2019

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A sulfur‐promoted three‐component reaction of isatoic anhydride, primary aliphatic or aromatic amines, and acetophenones leading to densely substituted 3‐substituted 2‐aroylquinazolin‐4(3H)‐ones is reported. The key step involves a cascade reaction of selective oxidation of the methyl group of the acetophenones, followed by a condensation with anthranilamides. The scope of the reaction is applicable to the synthesis of tryptanthrin and various 3‐unsubstituted 2‐aroylquinazolin‐4(3H)‐ones.magnified image

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Metal‐Free, Photoredox‐Catalyzed Synthesis of Quinazolin‐4(3H)‐ones and Benzo[4,5]imidazo[1,2‐c]quinazolines Using Trialkylamines as Alkyl Synthon

et al. 2023

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Highly functionalized quinazolin‐4(3H)‐ones were synthesized from reactions of N‐aryl‐2‐aminobenzamides with trialkylamines under photocatalytic conditions by using eosin Y (EY) as a catalyst. The reaction proceeds under mild conditions in aqueous acetonitrile and has a broad substrate scope. Mechanistic studies disclosed the electron‐donor nature of the intermediate 2,3‐dihydroquinazolin‐4(1H)‐one (3’) in the photocatalytic cycle to afford the 2,3‐disubstituted‐quinazolin‐4(3H)‐ones (3). This methodology has been extended to synthesize benzo [4,5] imidazole[1,2‐c] quinazolines and 3 aa on a large scale. Furthermore, the synthesis of potent central nervous system depressant (CNS) drug molecules such as methaqualone (3 la) and mecloqualone (3 pa) was also achieved successfully.

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Copper-Catalyzed Tandem Reaction of 2-Aminobenzamides with Tertiary Amines for the Synthesis of Quinazolinone Derivatives

Cited by 12 publications

References 6 publications

One-Pot Three-Component Reaction for the Synthesis of 3,4-Dihydroquinazolines and Quinazolin-4(3H)-ones

One-Pot Three-Component Reaction for the Synthesis of 3,4-Dihydroquinazolines and Quinazolin-4(3H)-ones

Sulfur‐Promoted Synthesis of 2‐Aroylquinazolin‐4(3H)‐ones by Oxidative Condensation of Anthranilamide and Acetophenones

Metal‐Free, Photoredox‐Catalyzed Synthesis of Quinazolin‐4(3H)‐ones and Benzo[4,5]imidazo[1,2‐c]quinazolines Using Trialkylamines as Alkyl Synthon

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