Synthesis of <i>N</i>‐Sulfonyl Pyrazoles Through Cyclization Reactions of Sulfonyl Hydrazines with Enaminones Promoted by <i>p</i>‐TSA

Zhang, Qiaohe; Hu, Biao; Zhao, Yuxuan; Zhao, Siyun; Wang, Yanqin; Zhang, Biao; Yan, Sheng‐Jiao; Yu, Fuchao

doi:10.1002/ejoc.201901886

Cited by 31 publications

(11 citation statements)

References 65 publications

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“…Due to the chemical diversity of organic spacer cations, metal ions, and halide anions and their absorption/emission properties and photochemical stability, two-dimensional (2D) organic-inorganic perovskites have emerged for photodetectors, [1,2] optoelectronic, [3][4][5][6] lasers, [7][8][9] electroluminescence, [10,11] and spintronics. [12][13][14] Multiple quantum well structures of twodimensional (2D) perovskite materials, in which inorganic octahedra networks are alternately stacked with organic cation spacers, offer them an ideal platform for structural diversity and novel functionalities. [15][16][17][18] Attributed to the fact that the cesium cation Cs + (167 pm) has a smaller ionic radius than the methyl ammonium cation (MA) + (217 pm) cations, the perovskite crystal lattice contraction is expected.…”

Section: Introductionmentioning

confidence: 99%

Single Crystals of Mixed‐Cation Copper‐Based Perovskite with Trimodal Bandgap Behavior

Elattar

Suzuki

et al. 2022

Chemistry A European J

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Two‐dimensional (2D) hybrid perovskites with novel functionalities and structural diversity are a perfect platform for emerging optoelectronic devices such as photodetectors, light‐emitting diodes, and solar cells. Here, we demonstrate that excess concentration of Cesium bromide (CsBr) is key to the formation of easily exfoliated 2D Cs2Cu(Cl/Br)4 perovskite crystal. Furthermore, by employing this trick to 2D perovskite MA2Cu(Cl/Br)4 (MA=methylammonium), we achieve a phase‐pure easily exfoliated 2D mixed‐cation (MA/Cs)2Cu(Cl/Br)4 perovskite crystal, which exhibits reduced bandgap (1.53 eV) with ferromagnetic behavior and photovoltaic property. The resultant mixed‐cation structured device reveals enhanced efficiency compared to all MA and all Cs counterparts. These findings demonstrate the importance of cation‐engineering in developing innovative materials with novel properties.

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Section: Introductionmentioning

confidence: 99%

Single Crystals of Mixed‐Cation Copper‐Based Perovskite with Trimodal Bandgap Behavior

Elattar

Suzuki

et al. 2022

Chemistry A European J

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“…Recently, our group and Wan's group independently reported a facile approach for the synthesis of N-sulfonyl pyrazoles from readily available sulfonyl hydrazines and N,Ndimethyl enaminones under p-TSA-promoted and I 2 -catalyzed conditions, respectively (Scheme 31). 33,34 In our work, condensation of the carbonyl group of the N,N-dimethyl…”

Section: Synthesis Of Five-membered Heterocyclesmentioning

confidence: 83%

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Huang

2020

Synthesis

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Enaminones are gaining increasing interest because of their unique properties and their importance in organic synthesis as versatile building blocks. N,N-Dimethyl enaminones offer a better leaving group (a dimethylamine group) than other enaminones, and allow further elaboration via a range of facile chemical transformations. Over the past five years, there have been an increasing number of reports describing the synthetic applications of N,N-dimethyl enaminones. This review provides a comprehensive overview on the synthetic applications of N,N-dimethyl enaminones that have been reported since 2016.1 Introduction2 Direct C(sp2)–H α-Functionalization2.1 Synthesis of α-Sulfenylated N,N-Dimethyl Enaminones2.2 Synthesis of α-Thiocyanated N,N-Dimethyl Enaminones2.3 Synthesis of α-Acyloxylated N,N-Dimethyl Enaminones3 Functionalization Reactions via C=C Double Bond Cleavage3.1 Synthesis of Functionalized Methyl Ketones3.2 Synthesis of α-Ketoamides, α-Ketoesters and 1,2-Diketones3.3 Synthesis of N-Sulfonyl Amidines4 Construction of All-Carbon Aromatic Scaffolds4.1 Synthesis of Benzaldehydes4.2 Synthesis of the Naphthalenes5 Construction of Heterocyclic Scaffolds5.1 Synthesis of Five-Membered Heterocycles5.2 Synthesis of Six-Membered Heterocycles5.3 Synthesis of Quinolines 5.4 Synthesis of Functionalized Chromones5.5 Synthesis of Other Fused Polycyclic Heterocycles6 Conclusions and Perspectives

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“…Also, some of our reported N-arylsulfonylpyrazole derivatives (Elgemeie et al, 1998(Elgemeie et al, , 2013Elgemeie & Hanfy, 1999) proved to be inhibitors of the NS2B-NS3 virus and the enzyme cathepsin B16 (Myers et al, 2007;Sidique et al, 2009). In a continuation of our research investigating new approaches to other new derivatives of N-sulfonylpyrazoles, seeking various scaffolds for use as encouraging chemotherapeutics (Zhang et al, 2020;Elgemeie & Jones, 2002), we have now synthesized the N1-substituted derivative of N-sulfonylpyrazole 1 (the structure of which we have reported; Elgemeie et al, 2013).…”

Section: Chemical Contextmentioning

confidence: 91%

Crystal structure of ethyl 2-(3-amino-5-oxo-2-tosyl-2,5-dihydro-1H-pyrazol-1-yl)acetate

2021

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In the title compound, C14H17N3O5S, the five-membered ring is essentially planar. The substituents at the nitrogen atoms subtend a C—N—N—S torsion angle of −95.52 (6)°. The amino group forms an intramolecular hydrogen bond to a sulfonyl oxygen atom; two intermolecular hydrogen bonds from the amino group, to the other S=O group and to the oxo substituent, form a layer structure parallel to the ab plane. The structure determination confirms that the title compound is N- rather than O-alkylated.

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Synthesis of N‐Sulfonyl Pyrazoles Through Cyclization Reactions of Sulfonyl Hydrazines with Enaminones Promoted by p‐TSA

Cited by 31 publications

References 65 publications

Single Crystals of Mixed‐Cation Copper‐Based Perovskite with Trimodal Bandgap Behavior

Single Crystals of Mixed‐Cation Copper‐Based Perovskite with Trimodal Bandgap Behavior

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Crystal structure of ethyl 2-(3-amino-5-oxo-2-tosyl-2,5-dihydro-1H-pyrazol-1-yl)acetate

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