Ru‐Catalyzed C(sp<sup>2</sup>)−H Bond Arylation of Benzamides Bearing a Novel 4‐Aminoantipyrine as a Directing Group

Mamari, Hamad H. Al; Kiumi, Diana Al; Rashdi, Tamadher Al; Quraini, Huda Al; Rashdi, Malak Al; Sheraiqi, Sumayya Al; Harmali, Sara Al; Lamki, Mohammed Al; Sheidi, Ahmed Al; Zadjali, Asma Al

doi:10.1002/ejoc.202100513

Eur J Org Chem

2021

DOI: 10.1002/ejoc.202100513

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Ru‐Catalyzed C(sp²)−H Bond Arylation of Benzamides Bearing a Novel 4‐Aminoantipyrine as a Directing Group

Hamad H. Al Mamari

Diana Al Kiumi

Tamadher Al Rashdi

et al.

Abstract: A novel design-based removable N,O-bidentate directing group based on cheap and commercially available 4-aminoantipyrine (AAP) is reported. Aromatic AP amides bearing 4-aminoantipyrine underwent efficient Ru-catalyzed C(sp 2 )À H arylation using [RuCl 2 (PPh 3 ) 3 ] as a catalyst and aryl bromides as electrophiles. The novel bidentate directing group enabled the CÀ H functionalization reaction with good scope, good functional group tolerance and in decent yields.

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High-throughput crystallization and crystal structure of N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-methylbenzamide: a benzamide bearing the 4-aminoantipyrine moiety

Al Mamari,

Al Sulaimi,

Mardiana

et al. 2024

Acta Crystallogr C Struct Chem

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A recent communication on Ru-catalyzed C—H bond arylation with 4-aminoantipyrine (AP) reported the synthesis of AP benzamides. In order to provide additional support to the published structures of AP benzamides, crystallization by high-throughput (HTP) encapsulated nanodroplet crystallization (ENaCt) was undertaken. This allowed for conclusive structure determination by single-crystal X-ray diffraction analysis (SCXRD). This article describes the crystallization and X-ray crystal structure of N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-methylbenzamide, C19H19N3O2, as a benzamide bearing 4-aminoantipyrine, providing structural confirmation. X-ray structure analysis reveals intermolecular hydrogen-bonding interactions between the AP benzamide N—H proton and the carbonyl O atom of the AP moiety.

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High-throughput crystallization and crystal structure of N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-methylbenzamide: a benzamide bearing the 4-aminoantipyrine moiety

Al Mamari,

Al Sulaimi,

Mardiana

et al. 2024

Acta Crystallogr C Struct Chem

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show abstract

Synthesis, In Silico Studies, Antimicrobial, Antioxidant Activities, Docking Simulation, and Computational Analysis of Novel Acrylamide Derivatives

Bayrak,

Fahim,

Boyraci

et al. 2024

Russ J Gen Chem

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Ru‐Catalyzed C(sp²)−H Bond Arylation of Benzamides Bearing a Novel 4‐Aminoantipyrine as a Directing Group

Cited by 2 publications

References 96 publications

High-throughput crystallization and crystal structure of N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-methylbenzamide: a benzamide bearing the 4-aminoantipyrine moiety

High-throughput crystallization and crystal structure of N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-methylbenzamide: a benzamide bearing the 4-aminoantipyrine moiety

Synthesis, In Silico Studies, Antimicrobial, Antioxidant Activities, Docking Simulation, and Computational Analysis of Novel Acrylamide Derivatives

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Ru‐Catalyzed C(sp2)−H Bond Arylation of Benzamides Bearing a Novel 4‐Aminoantipyrine as a Directing Group

Cited by 2 publications

References 96 publications

High-throughput crystallization and crystal structure of N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-methylbenzamide: a benzamide bearing the 4-aminoantipyrine moiety

High-throughput crystallization and crystal structure of N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-methylbenzamide: a benzamide bearing the 4-aminoantipyrine moiety

Synthesis, In Silico Studies, Antimicrobial, Antioxidant Activities, Docking Simulation, and Computational Analysis of Novel Acrylamide Derivatives

Contact Info

Product

Resources

About

Ru‐Catalyzed C(sp²)−H Bond Arylation of Benzamides Bearing a Novel 4‐Aminoantipyrine as a Directing Group