Palladium‐Catalyzed Tandem Reaction of Quinazolinone‐Based Nitriles with Arylboronic Acids: Synthesis of 2‐(4‐Arylquinazolin‐2‐yl)anilines

Zhang, Yetong; Shao, Yinlin; Gong, Julin; Hu, Kun; Cheng, Tanyu; Chen, Jiuxi

doi:10.1002/adsc.201800615

Cited by 36 publications

(14 citation statements)

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“…Many 3,4-dihydroquinazolin-2(1 H )-one derivatives have been previously synthesized (Huang et al, 2008; Khan et al, 2014, 2015, 2016; Kshirsagar, 2015; Camacho et al, 2016; Maiden and Harrity, 2016; Awad et al, 2018; Zhang et al, 2018; Elkholy et al, 2019; Gatadi et al, 2019; Long et al, 2019; Wang et al, 2019). For example, Wang et al (2009) reported the synthesis of 4-alkyl-2(1H)-quinazolinones via the cyclization of 1-(2-alkynyl-phenyl)ureas catalyzed by TfOH and Saunthwal et al (2015) described a green and catalyst-free straightforward tandem synthesis of functionalized tetrahydroquinazolines from 2-aminophenylacrylate.…”

Section: Introductionmentioning

confidence: 99%

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

et al. 2019

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A new series of 3-substituted 4-methylene-quinazolinthiones and 4-methylene-quinazolinones were synthesized in moderate to excellent yield through a simple reaction of 2-aminoacetophenones with isocyanates or isothiocyanates. The reaction shows good tolerance of many important functional groups in the presence of air and water under metal-free conditions. Only water is produced as a coproduct, rendering this “green” methodology a highly versatile and eco-friendly alternative to the existing methods for the construction of the quinazolinone/quinazolinthione framework. We have interpreted the reaction mechanism by use of quantum chemical calculations on the basis of state-of-the-art computational methods SMD-B3LYP-D3(BJ)/BS1//B3LYP/BS1.

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Section: Introductionmentioning

confidence: 99%

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

et al. 2019

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“…A similar combination of reactions has been extended to the synthesis of quinazolines by using quinazolinone-based aryl nitriles as the substrates (Scheme 28). 39 In this reaction, the mechanism is almost the same as that of their previous synthetic approach for the synthesis of isoquinolines, 37 except for the ring-opening by a nucleophile and subsequent hydrolytic quenching of the imine moiety to obtain the desired quinazolines with an aniline substituent (Scheme 29).…”

Section: Scheme 27 Proposed Mechanism For the Pd-catalyzed Formation mentioning

confidence: 88%

Synthesis of N-Heterocycles via Transition-Metal-Catalyzed Tandem Addition/Cyclization of a Nitrile

Hsieh

2020

Synthesis

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The diverse methodologies to synthesize N-heterocycles through transition-metal-catalyzed cascade addition/cyclization of a nitrile are discussed in this review. Aspects relating to three types of transition-metal-catalyzed addition of a nitrile with subsequent cyclization include (1) a transition-metal acting as a Lewis acid to accelerate the nucleophilic addition of a nitrile, (2) the late-transition-metal-catalyzed 1,2-insertion of a nitrile, and (3) an in situ generated radical by transition-metal catalysis to implement a radical addition/cyclization tandem reaction. Applications for the synthesis of natural alkaloids, their derivatives, and some bioactive compounds are also summarized herein.1 Introduction2 Nucleophilic Addition of a Nitrile Accelerated by a Lewis Acid2.1 Late-Transition-Metal Catalysis2.2 Early-Transition-Metal Catalysis2.3 Lanthanide-Metal Catalysis2.4 Cyclization from N-Arylnitriliums3 Transition-Metal-Catalyzed Insertion of a Nitrile4 Transition-Metal-Catalyzed Radical Addition of a Nitrile5 Conclusions

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“…Later, the same research group disclosed another methodology for quinazoline scaffolds 65 from reaction of aryl boronic acids 61 with 2-(quinazolinone-3(4 H )-yl)benzonitriles 64 . This tandem synthesis involved nucleophilic addition, followed by intramolecular cyclization and subsequent ring-opening, delivering the corresponding product in moderate to excellent isolated yields (31–93%) ( Scheme 21C ) (Zhang et al, 2018 ). In another interesting report by Chen et al, the synthesis of 2,4-disubstituted quinazoline derivatives 66 through Pd–catalyzed reaction of aryl boronic acids 61 with N -(2-cyanoaryl)benzamides 60 by employing 1,10-phen, trifluoroacetic acid in THF at 80°C has been described ( Scheme 21D ).…”

Section: Transition Metal-catalyzed Methodologiesmentioning

confidence: 99%

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Faisal

Saeed

2021

Front. Chem.

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In medicinal chemistry, one of the most significant heterocyclic compounds are quinazolines, possessing broad range of biological properties such as anti-bacterial, anti-fungal, anti-HIV, anti-cancer, anti-inflammatory, and analgesic potencies. Owing to its numerous potential applications, in the past two decades, there is an increase in the importance of designing novel quinazolines, exploring promising routes to synthesize quinazolines, investigating different properties of quinazolines, and seeking for potential applications of quinazolines. The present review article describes synthesis of quinazolines via eco-friendly, mild, atom-efficient, multi-component synthetic strategies reported in the literature. The discussion is divided into different parts as per the key methods involved in the formation of quinazoline skeletons, aiming to provide readers an effective methodology to a better understanding. Consideration has been taken to cover the most recent references. Expectedly, the review will be advantageous in future research for synthesizing quinazolines and developing more promising synthetic approaches.

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Palladium‐Catalyzed Tandem Reaction of Quinazolinone‐Based Nitriles with Arylboronic Acids: Synthesis of 2‐(4‐Arylquinazolin‐2‐yl)anilines

Cited by 36 publications

References 50 publications

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

Synthesis of N-Heterocycles via Transition-Metal-Catalyzed Tandem Addition/Cyclization of a Nitrile

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

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