Metal-free tandem Beckmann–electrophilic aromatic substitution cascade affording diaryl imines, ketones, amines, and quinazolines

Sarsah, Samuel Robert Smith; Lutz, Marlon R.; Bobb, Kailyn Chichi; Becker, Daniel P.

doi:10.1016/j.tetlet.2015.07.095

Cited by 7 publications

(2 citation statements)

References 18 publications

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“…[2] Therefore, considerable effort has been devoted to the development of effective approaches to the establishment of tetrahydroquinazoline derivatives. In recent years, different synthetic protocols for tetrahydroquinazoline derivatives have been developed using Bronsted acid, [3] p-toluenesulfonic acid (p-TSA), [4] iodine, [5] tin(II) chloride dehydrate, [6] triphenylphosphine gold(I) triflate, [7] iron, [8] copper(II) acetate monohydrate, [9] potassium carbonate, [10] acetic acid, [11] Oxone, [12] sodium acetate, [13] and sodium tetrahydrobo-rate [14] as catalysts. These protocols have greatly improved and enriched access to tetrahydroquinazoline derivatives.…”

Section: Introductionmentioning

confidence: 99%

New Use of Non-natural Catalytic Activity of Pepsin: Highly Efficient Synthesis of Tetrahydroquinazolines

Jiang¹,

Lu²,

Li³

et al. 2020

Chin. J. Org. Chem.

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Pepsin from porcine gastric mucosa has a non-natural ability to catalyze the cyclocondensation of aromatic amines and 2-aminobenzaldehyde. The corresponding tetrahydroquinazolines were obtained in good yields (41%～95%) in aqueous methanol solution. The catalytic activity of pepsin was evaluated by investigating solvent, temperature, enzyme loading, and substrate ratio in the enzyme-catalyzed reaction. Herein, a potential biocatalytic approach as an alternative to chemical synthesis for tetrahydroquinazoline derivatives was proposed.

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Section: Introductionmentioning

confidence: 99%

New Use of Non-natural Catalytic Activity of Pepsin: Highly Efficient Synthesis of Tetrahydroquinazolines

Jiang¹,

Lu²,

Li³

et al. 2020

Chin. J. Org. Chem.

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“…A well-established method is the direct condensation of the amine with a carbonyl compound often in the presence of a Lewis acid . Other efficient methods include oxidative self-condensation of amines, oxidative coupling of amines and alcohols, hydroamination of alkynes or alkenes, with amines, and tandem Beckmann–electrophilic aromatic substitution (TB-EAS) of benzophenone oximes . In addition, N -arylketimines can also be accessed from the reaction of ketones with different reagents such as N,N -bis(trimethylsilyl)amines, PhN(AlCl 2 ) 2 , and ArN(MgBr) 2 .…”

Section: Introductionmentioning

confidence: 99%

Preparation of Ketimines from Aryldiazonium Salts, Arenes, and Nitriles via Intermolecular Arylation of N-Arylnitrilium Ions

et al. 2018

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A transition-metal-free approach for the preparation of N-arylketimines has been developed from the direct reaction of aryldiazonium salts, arenes, and nitriles in a one-pot fashion with the consecutive formation of N-C and C-C bonds. This approach proceeds via an in situ generation of N-arylnitrilium intermediate, which then undergoes intermolecular arylation. This three-component strategy offers a step- and atom-efficient way to N-arylketimines from easily accessible reagents under mild reaction conditions. The characterization of stereochemistry of ketimine was achieved by X-ray crystallographic structure and theoretical calculation. Operational simplicity, shorter reaction time, excellent functional group compatibility, and scalability are the key features of this report.

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Ritter-Type Reaction

Zhang,

Chen,

Gan

2024

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Metal-free tandem Beckmann–electrophilic aromatic substitution cascade affording diaryl imines, ketones, amines, and quinazolines

Cited by 7 publications

References 18 publications

New Use of Non-natural Catalytic Activity of Pepsin: Highly Efficient Synthesis of Tetrahydroquinazolines

New Use of Non-natural Catalytic Activity of Pepsin: Highly Efficient Synthesis of Tetrahydroquinazolines

Preparation of Ketimines from Aryldiazonium Salts, Arenes, and Nitriles via Intermolecular Arylation of N-Arylnitrilium Ions

Ritter-Type Reaction

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