Copper-Catalyzed Synthesis of Substituted Quinazolines from Benzonitriles and 2-Ethynylanilines via Carbon–Carbon Bond Cleavage Using Molecular Oxygen

Wang, Xu; He, Dandan; Huang, Yubing; Fan, Qi-Hang; Wu, Wanqing; Jiang, Huanfeng

doi:10.1021/acs.joc.8b00378

Cited by 49 publications

(34 citation statements)

References 59 publications

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“…With benefits such as mild reaction conditions, simple synthetic procedures, and readily available starting materials, the technique developed could be considered as a promising technique. Further, very recently, Wang et al published Cu-catalyzed one-pot process for the preparation of substituted quinazolines 81 by reaction of 2-ethynylanilines 79 with benzonitriles 80 using O 2 as the sole oxidant (Wang et al, 2018). The reaction proceeded via effective cleavage of the carbon-carbon triple bond and formation of new carbon-nitrogen, and carbon-carbon bonds in a one-pot manner (Scheme 22F).…”

Section: Copper-mediated Catalytic Systemsmentioning

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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Section: Copper-mediated Catalytic Systemsmentioning

confidence: 99%

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Faisal

Saeed

2021

Front. Chem.

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“…The appropriate solvent and amount were determined for the effective catalysis.T he reaction could take place either toluene or methanol ( Table 1, entries 1-3). Ther eaction did not proceed in the presence of UiO-67-BPY alone (Table S1, entries [11][12][13][14][15][16][17][18] or Zn(BF 4 ) 2 ·x H 2 Oa lone (entries 27 and 28). Unsurprisingly,w ith lower amounts of Zn-UiO-67-BPY,t he yield decreased (entries 6-10).…”

Section: Zuschriftenmentioning

confidence: 99%

A Reusable MOF‐Supported Single‐Site Zinc(II) Catalyst for Efficient Intramolecular Hydroamination of o‐Alkynylanilines

Zhou

et al. 2019

Angewandte Chemie

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The exploitation of new and active earth-abundant metal catalysts is critical for sustainable chemicalp roduction. Herein, we demonstrate the design of highly efficient, robust, and reusable Zn II -bipyridine-based metal-organic framework (MOF) catalysts for the intramolecular hydroamination of oalkynylanilines to indoles.U nder similar conditions homogeneous catalytic systems mainly provide hydrolysate.O ur results prove that MOFs support unique internal environments that can affect the direction of chemical reactions.T he Zn IIcatalyzedh ydroamination reaction can be conducted without additional ligands,b ase,o ra cid, and is thus av ery clean reaction system with regardtoi ts environmental impact. Scheme 1. a) Previous hydroamination methods and b) the proposed MOF-supported single-site zinc catalyst for the intramolecular hydroamination of o-alkynylanilines.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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“…As illustrated in Fig. 2B, in the nucleophilic addition of nitriles, the most reported reaction partners have been focused on the highly reactive nitrogen, [44][45][46][47][48][49][50][51][52] oxygen, [53][54][55][56][57][58][59][60][61] and sulfur nucleophiles till now. [62][63][64] For carbon pronucleophiles, the related studies are only limited to sp, sp 2 , and sp 3 with α-electron withdrawing group (i.e.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of densely substituted pyridine derivatives from nitriles by a non-classical [4+2] cycloaddition/1,5-hydrogen shift strategy

Wu¹,

He²,

Duan³

et al. 2021

Preprint

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A novel strategy has been established to assemble an array of densely substituted pyridine derivatives from nitriles and o-substituted aryl alkynes or 1-methyl-1,3-enynes via a non-classical [4 + 2] cycloaddition along with 1,5-hydrogen shift process. The well-balanced affinities of two different alkali metal salts enable the C(sp3)-H bond activation as well as the excellent chemo- and regioselectivities. This protocol offers a new guide to construct pyridine frameworks from nitriles with sp3-carbon pronucleophiles, and shows potential applications in organic synthesis and medicinal chemistry.

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Copper-Catalyzed Synthesis of Substituted Quinazolines from Benzonitriles and 2-Ethynylanilines via Carbon–Carbon Bond Cleavage Using Molecular Oxygen

Cited by 49 publications

References 59 publications

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

Chemical Insights Into the Synthetic Chemistry of Quinazolines: Recent Advances

A Reusable MOF‐Supported Single‐Site Zinc(II) Catalyst for Efficient Intramolecular Hydroamination of o‐Alkynylanilines

Synthesis of densely substituted pyridine derivatives from nitriles by a non-classical [4+2] cycloaddition/1,5-hydrogen shift strategy

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