DBU-Promoted Facile, Chemoselective Cleavage of Acetylenic TMS Group

Yeom, Chang-Eun; Kim, Mi Jeong; Choi, Whail; Kim, B. Moon

doi:10.1055/s-2008-1032078

Cited by 4 publications

(1 citation statement)

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“…8a,28a Nevertheless, one cannot exclude a priori chance of the substrate desilylation because of the influence of hydrazine as a base. 33 For determining conditions of the 3-alkynylpyrazolines selective synthesis, we have examined interactions of easily available 8c,14,34 enynones 1 with a wide variety of monosubstituted hydrazines 2 (Figure 2). Substituents in the substrates 1a-n were chosen consistently by selection of their electronic and steric effects.…”

Section: Paper Synthesismentioning

confidence: 99%

Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs

Golovanov,

Odin,

Gordon

et al. 2023

Synthesis

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On the basis of the selective reactions of hydrazines with trialkylsilyl-substituted cross-conjugated enynones (pent-1-en-4-yn-3-ones) as fundamental building blocks, this work presents the developed common methodology for the synthesis of polysubstituted luminescent derivatives of acetylenic pyrazolines, pyrazoles, and combined polyheterocycles containing structural fragments from pyrazolines, isoxazoles, thiophenes, thiazoles, benzo[d]thiazoles, and benzo[d]imidazoles. In reactions with hydrazine and its monosubstituted aromatic and heteroaromatic derivatives, the mentioned pent-1-en-4-yn-3-ones, containing Me3Si, Et3Si, and t-BuMe2Si groups at the triple bond, give 3-(trialkylsilyl)ethynylpyrazolines. Following stages of desilylation and 1,3-dipolar cycloaddition with nitrile oxides, the 3-(trialkylsilyl)ethynylpyrazolines provide the formation of combined polyheterocyclic derivatives. Thus, a one-pot synthetic route to pyrazoline-containing isoxazoles from cross-conjugated enynones, arylhydrazines, and α-chlorobenzaldoximes has been developed. Some aspects of cyclocondensation mechanism and luminescent properties of synthesized azoles derivatives were examined.

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Section: Paper Synthesismentioning

confidence: 99%

Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs

Golovanov,

Odin,

Gordon

et al. 2023

Synthesis

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ChemInform Abstract: DBU‐Promoted Facile, Chemoselective Cleavage of Acetylenic TMS Group.

et al. 2008

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Identification of a Covalent Importin-5 Inhibitor, Goyazensolide, from a Collective Synthesis of Furanoheliangolides

et al. 2021

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Sesquiterpenes are a rich source of covalent inhibitors with a long history in traditional medicine and include several important therapeutics and tool compounds. Herein, we report the total synthesis of 16 sesquiterpene lactones via a build/couple/pair strategy, including goyasensolide. Using an alkyne-tagged cellular probe and proteomics analysis, we discovered that goyazensolide selectively targets the oncoprotein importin-5 (IPO5) for covalent engagement. We further demonstrate that goyazensolide inhibits the translocation of RASAL-2, a cargo of IPO5, into the nucleus and perturbs the binding between IPO5 and two specific viral nuclear localization sequences.

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DBU-Promoted Facile, Chemoselective Cleavage of Acetylenic TMS Group

Cited by 4 publications

References 1 publication

Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs

Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs

ChemInform Abstract: DBU‐Promoted Facile, Chemoselective Cleavage of Acetylenic TMS Group.

Identification of a Covalent Importin-5 Inhibitor, Goyazensolide, from a Collective Synthesis of Furanoheliangolides

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