Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source

Yan, Yiyan; Xu, Xiaohe; Jie, Xiaokang; Cheng, Jingya; Bai, Renren; Shuai, Qi; Xie, Yuanyuan

doi:10.1016/j.tetlet.2018.06.011

Cited by 5 publications

(5 citation statements)

References 44 publications

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“…Cinnamamides 2a-h were efficiently prepared from cinnamic acids 1a-h through a two-step procedure. [19][20][21] The acids were converted to their succinic esters using EDC•HCl and N-hydroxysuccinimide (NHS) in CH 2 Cl 2 at room temperature. The crude active ester was subsequently converted to the corresponding amide after slow addition of 25% aq.…”

Section: Chemistrymentioning

confidence: 99%

Novel styryl-thiazole hybrids as potential anti-Alzheimer's agents

Gouleni,

Di Rienzo,

Yılmaz

et al. 2023

RSC Med. Chem.

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Section: Chemistrymentioning

confidence: 99%

Novel styryl-thiazole hybrids as potential anti-Alzheimer's agents

Gouleni,

Di Rienzo,

Yılmaz

et al. 2023

RSC Med. Chem.

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“…Acrylonitriles can be obtained from a wide variety of starting materials such as carbonyl compounds, alkynenitriles, vinyl halides, vinyl anions, alkynes, and alkenes. [ 59,60 ] The general synthetic routes for the preparation of acrylonitriles are shown in Figure 5.…”

Section: Synthetic Strategies Of Acrylonitrilesmentioning

confidence: 99%

“…It was found that when water was used as the solvent, α , β ‐unsaturated amides were obtained as the main product (Scheme 6). [ 60 ]…”

Section: Synthetic Strategies Of Acrylonitrilesmentioning

confidence: 99%

Insights into the chemistry and therapeutic potential of acrylonitrile derivatives

Tan

Zengin

2021

Archiv der Pharmazie

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Acrylonitrile is a fascinating scaffold widely found in many natural products, drugs, and drug candidates with various biological activities. Several drug molecules such as entacapone, rilpivirine, teriflunomide, and so forth, bearing an acrylonitrile moiety have been marketed. In this review, diverse synthetic strategies for constructing desired acrylonitriles are discussed, and the different biological activities and medicinal significance of various acrylonitrile derivatives are critically evaluated. The information gathered is expected to provide rational guidance for the development of clinically useful agents from acrylonitriles.

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“…α , β ‐unsaturated compounds can be prepared through Knoevenagel condensation reaction catalyzed by various materials such as metal–organic frameworks (MOFs), porous organic polymers, functionalized silica‐based compounds, and magnetic nanoparticle‐supported catalysts 4–7 . α , β ‐unsaturated nitriles are important chemicals for the preparation of pharmaceuticals and functional compounds, which can be synthesized via one‐pot reactions 8–11 . One‐pot tandem deacetalization‐Knoevenagel reaction has been explored for the straightforward preparation of α , β ‐unsaturated nitriles 12,13 .…”

Section: Introductionmentioning

confidence: 99%

“…[4][5][6][7] α,β-unsaturated nitriles are important chemicals for the preparation of pharmaceuticals and functional compounds, which can be synthesized via one-pot reactions. [8][9][10][11] Onepot tandem deacetalization-Knoevenagel reaction has been explored for the straightforward preparation of α,β-unsaturated nitriles. 12,13 For such a reaction, Lewis or Brønsted acid sites promote deacetalization step, while base centers can accelerate the Knoevenagel reaction.…”

Section: Introductionmentioning

confidence: 99%

A new 2D coordination polymer as bifunctional heterogeneous catalyst for tandem deacetalization‐Knoevenagel reaction

Najafi,

Janczak

2023

Applied Organom Chemis

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Designing multifunctional catalysts for one‐pot organic transformations is highly important due to economic and environmental point of views. Synthesis of bifunctional acid–base tandem catalysts has drawn attention owing to the incorporation of antagonistic active sites in a single catalyst. In the current work, a novel coordination polymer, [NaZn(btc)(H2O)3].1.5H2O (1) (1,3,5‐benzenetricarboxylic acid [H3btc]), was prepared by solvothermal method. Single crystal analysis of 1 revealed that the structure is two dimensional and contains the coexisted Lewis acid–base sites. The material was further characterized by powder X‐ray diffraction, FT‐IR, thermogravimetric analysis, and temperature programed desorption of NH3 (NH3‐TPD) and CO2 (CO2‐TPD). Compound 1 was utilized as a heterogeneous catalyst for tandem deacetalization‐Knoevenagel reaction of benzaldehyde dimethyl acetal and malononitrile. It exhibited good activity and structural stability during the reaction.

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Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source

Cited by 5 publications

References 44 publications

Novel styryl-thiazole hybrids as potential anti-Alzheimer's agents

Novel styryl-thiazole hybrids as potential anti-Alzheimer's agents

Insights into the chemistry and therapeutic potential of acrylonitrile derivatives

A new 2D coordination polymer as bifunctional heterogeneous catalyst for tandem deacetalization‐Knoevenagel reaction

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