Synthesis of 2<i>H</i>-Chromene-4-Carbonitriles Via Trimethylsilyl Cyanide

Ren, Demin; Liu, Hexiu; Huang, Yangen; Fu, Xin; Li, Xiaofang

doi:10.3184/174751918x15287198150613

Cited by 4 publications

(1 citation statement)

References 18 publications

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“…The 2-aryl-2H-chromene-4-carbonitriles were reported ( Figure 4R ) under the TMSCN catalysis in the presence of tetrabutylammonium fluoride, followed by a Michael addition/elimination pathway, which led to give the moderate yields of products (Ren et al, 2018 ).…”

Section: Synthetic Strategies Of 2h/4h-chromenesmentioning

confidence: 99%

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2020

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2H/4H-chromene (2H/4H-ch) is an important class of heterocyclic compounds with versatile biological profiles, a simple structure, and mild adverse effects. Researchers discovered several routes for the synthesis of a variety of 2H/4H-ch analogs that exhibited unusual activities by multiple mechanisms. The direct assessment of activities with the parent 2H/4H-ch derivative enables an orderly analysis of the structure-activity relationship (SAR) among the series. Additionally, 2H/4H-ch have numerous exciting biological activities, such as anticancer, anticonvulsant, antimicrobial, anticholinesterase, antituberculosis, and antidiabetic activities. This review is consequently an endeavor to highlight the diverse synthetic strategies, synthetic mechanism, various biological profiles, and SARs regarding the bioactive heterocycle, 2H/4H-ch. The presented scaffold work compiled in this article will be helpful to the scientific community for designing and developing potent leads of 2H/4H-ch analogs for their promising biological activities.

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Section: Synthetic Strategies Of 2h/4h-chromenesmentioning

confidence: 99%

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2020

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Multicomponent Cyanation of 2‐Amino‐3‐cyano‐4H‐chromenes in Aqueous Media

Ardevines,

Garcés‐Marín,

Cervantes‐Cerrada

et al. 2024

Asian J Org Chem

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Chromenes represent a pivotal molecular structure found in a diverse range of biologically active compounds. Specifically, derivatives of 2‐amino‐3‐cyano‐4H‐chromene have demonstrated pharmacological applications, displaying potential antioxidant and anticancer activities. This has heightened interest in the exploration of new and more efficient methods for their synthesis. In recent years, few examples have emerged, focusing on the organocatalytic and enantioselective synthesis of 2‐amino‐3‐cyano‐4H‐chromene derivatives, although the overall number of works to date is limited. In this study, we present the results of the synthesis of 2‐amino‐4H‐chromen‐3,4‐dicarbonitriles through a Michael addition of cyanide to 2‐iminochromenes. To achieve this, we utilized a mild source of cyanide (acetone cyanohydrin), green solvents and catalytic conditions at room temperature, via a multicomponent approach. Furthermore, we initiated the enantioselective study of this process using chiral organocatalysts obtaining promising preliminary results.

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Organosilicon azoles: Structure, silylotropy and NMR spectroscopy

Ларина

2021

Advances in Heterocyclic Chemistry

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Synthesis of 2H-Chromene-4-Carbonitriles Via Trimethylsilyl Cyanide

Cited by 4 publications

References 18 publications

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

Multicomponent Cyanation of 2‐Amino‐3‐cyano‐4H‐chromenes in Aqueous Media

Organosilicon azoles: Structure, silylotropy and NMR spectroscopy

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