One-Pot Tandem Synthesis of 2-Arylquinazolines by a Multicomponent Cyclization Reaction

Ye, Leping; Yu, Lin; Zhu, Lijun; Xia, Xiaodong

doi:10.3390/molecules181113860

Cited by 18 publications

(7 citation statements)

References 26 publications

(42 reference statements)

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“…2- [ 4- ( Trifluoromethyl ) phenyl ] quinazoline ( 3ar ) [CAS no. 1208259-10-2] ( Ye et al, 2013 ). Yellow solid, 553.0 mg, 67% yield; 1 H NMR (400 MHz, CDCl 3 ): δ 9.39 (s, 1H), 8.69 (d, J = 8.2 Hz, 2H), 8.05 (d, J = 9.1 Hz, 1H), 7.90–7.86 (m, 2H), 7.74 (d, J = 8.2 Hz, 2H), 7.59 (m, 1H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ): δ 160.6, 159.6, 150.7, 141.3, 134.4, 132.2 (m), 128.9, 128.8, 127.9, 127.2, 125.5 (m), 123.8, 123.0.…”

Section: Methodsmentioning

confidence: 99%

“…7,158.9,150.6,149.2,143.9,134.6,129.4,128.8,128.3,127.2,123.9,phenyl]quinazoline (3ar) [CAS no. 1208259-10-2] (Ye et al, 2013). Yellow solid, 553.0 mg, 67% yield; 1 H NMR (400 MHz, CDCl 3 ): δ 9.39 (s, 1H), 8.69 (d, J 8.2 Hz, 2H), 8.05 (d, J 9.1 Hz, 1H), 7.90-7.86 (m, 2H), 7.74 (d, J 8.2 Hz, 2H), 7.59 (m, 1H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ): δ 160.…”

Section: General Informationmentioning

confidence: 99%

See 1 more Smart Citation

Metal-Free Synthesis of 2-Substituted Quinazolines via Green Oxidation of o-Aminobenzylamines: Practical Construction of N-Containing Heterocycles Based on a Salicylic Acid-Catalyzed Oxidation System

et al. 2022

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Conventional quinazoline synthesis methods involve a highly multistep reaction, and often require excess amounts of substrate to control the product selectivity, leading to significant resource wastage. Hence, in this study, from the viewpoint of green chemistry, we developed a novel metal-free synthetic method for 2-substituted quinazoline derivatives by the 4,6-dihydroxysalicylic acid-catalyzed oxidative condensation of o-aminobenzylamines and benzylamines using atmospheric oxygen. In this system, the use of a catalytic amount of BF3‧Et2O (10 mol%) as a Lewis acid successfully led to the efficient oxidative condensation and intramolecular cyclization of these amines, followed by aromatization to afford the corresponding 2-arylquinazolines in up to 81% yield with excellent atom economy and environmental factor. Furthermore, to expand this green oxidation method to gram-scale synthesis, we investigated the development of an oxidation process using salicylic acid itself as an organocatalyst, and established a method for the practical green synthesis of a series of nitrogen-containing heterocycles. We expect that the findings will contribute to the development of practical synthesis methods for pharmaceutical manufacturing and industrial applications, along with further advancements in green chemistry.

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Section: Methodsmentioning

confidence: 99%

Section: General Informationmentioning

confidence: 99%

Metal-Free Synthesis of 2-Substituted Quinazolines via Green Oxidation of o-Aminobenzylamines: Practical Construction of N-Containing Heterocycles Based on a Salicylic Acid-Catalyzed Oxidation System

et al. 2022

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“…A new one‐pot tandem protocol for the synthesis of a series of 2‐arylquinazolines from (2‐aminophenyl)methanol, aldehydes and ceric ammonium nitrate (CAN) has been reported . The initial reaction was performed using (2‐aminophenyl)methanol, benzaldehyde and CAN.…”

Section: Synthesis Of Heterocyclesmentioning

confidence: 99%

Copper‐Catalysed Multicomponent Syntheses of Heterocycles

Cherian¹,

Harry²,

Saranya³

et al. 2019

Asian J Org Chem

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Heterocycles cover a wide range of organic compounds and are ubiquitous in different areas of life sciences and technology. Multicomponent syntheses of heterocycles are very advantageous in comparison with the classical methods of heterocycle synthesis. In this review, copper-catalysed multicomponent reactions used for the synthesis of heterocycles published between 2004 and 2018 are summarised.[a] R. Scheme 1. Synthesis of 2-iminooxetanes and maleimides by Cu-catalysed three-component reaction and ring expansion respectively.

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“…Previously, various simple aryl-fused pyrimidines such as quinazolines were synthesized by using 2-(aminomethyl)anilines, (2-aminophenyl)methanol, 1-bromo-2-(bromomethyl)benzenes, (2-bromophenyl)methanamines, and 2-aminophenyl ketones as substrates under diverse conditions (Scheme ). In contrast, the present report describes a novel and efficient synthetic strategy to assemble pyrimidine-fused porphyrins through condensation of nickel(II) or copper(II) 2-( N , N -dimethylformamidine)-3-formyl-5,10,15,20-tetraarylporphyrins with ammonia followed by an intramolecular cascade aza-6π-annulation and aromatization (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Cascade Amination and Aza-6π-Annulation-Aromatization Strategy for the Synthesis of β-Pyrimidine-Fused Porphyrins

Singh

Nath

2023

J. Org. Chem.

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Novel nickel(II) and copper(II) complexes of 2-(N,N-dimethylformamidine)-3-formyl-5,10,15,20-tetraarylporphyrins have been synthesized for the first time from 2-aminoporphyrins under Vilsmeier−Haack conditions. These porphyrins are utilized as new building blocks to construct diverse β-pyrimidine-fused 5,10,15,20-tetraarylporphyrins in good yields via a cascade ammoniamediated condensation and intramolecular aza-6π-annulation/aromatization in 1,2-dichloroethane at 80 °C. Furthermore, copper(II) β-pyrimidine-fused porphyrins underwent demetallation in the presence of conc. H 2 SO 4 to afford free-base porphyrins, which on zinc insertion using Zn(OAc) 2 in CHCl 3 −MeOH provided zinc(II) β-pyrimidine-fused porphyrins in appreciable yields. Notably, these newly synthesized π-extended porphyrins displayed a modest bathochromic shift in their electronic absorption and emission spectra as compared to the traditional meso-tetraarylporphyrins. However, the protonated porphyrins (2a) and (3g) displayed a significant red-shifted absorption.

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One-Pot Tandem Synthesis of 2-Arylquinazolines by a Multicomponent Cyclization Reaction

Cited by 18 publications

References 26 publications

Metal-Free Synthesis of 2-Substituted Quinazolines via Green Oxidation of o-Aminobenzylamines: Practical Construction of N-Containing Heterocycles Based on a Salicylic Acid-Catalyzed Oxidation System

Metal-Free Synthesis of 2-Substituted Quinazolines via Green Oxidation of o-Aminobenzylamines: Practical Construction of N-Containing Heterocycles Based on a Salicylic Acid-Catalyzed Oxidation System

Copper‐Catalysed Multicomponent Syntheses of Heterocycles

Cascade Amination and Aza-6π-Annulation-Aromatization Strategy for the Synthesis of β-Pyrimidine-Fused Porphyrins

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