Base-Catalyzed Addition of Ketones to Alkynes as a Key Step in the One-Pot Synthesis of 1-Formyl-2-pyrazolines

Schmidt, Elena Yu.; Ivanova, Elena V.; Tatarinova, Inna V.; Semenova, Nadezhda V.; Ushakov, Igor А.; Трофимов, Б. А.

doi:10.1055/s-0034-1378687

Synthesis

2015

DOI: 10.1055/s-0034-1378687

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Base-Catalyzed Addition of Ketones to Alkynes as a Key Step in the One-Pot Synthesis of 1-Formyl-2-pyrazolines

Elena Yu. Schmidt

Elena V. Ivanova

Inna V. Tatarinova

et al.

Abstract: The reaction of ketones with alkynes in the presence of potassium tert-butoxide and dimethylsulfoxide followed by the treatment of the reaction mixture with hydrazine hydrate and formic acid leads to 2-pyrazoline-1-carbaldehydes in up to 81% yield.

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Cited by 9 publications

References 6 publications

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Selective P−C(sp³) Bond Cleavage and Radical Alkynylation of α‐Phosphorus Alcohols by Photoredox Catalysis

Jia

Chen

2018

Chemistry A European J

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Herein the first P-C(sp ) bond cleavage and radical alkynylation of α-phosphorus alcohols to construct phosphonoalkynes is reported. The phosphorus radical is generated upon P-C bond cleavage reaction via the alkoxyl radical through photoredox catalysis with cyclic iodine(III) reagents. Various arylphosphinoyl-, alkylphosphinoyl-, phosphonate-, and phosphonic amide alcohols serve as radical phosphorus precursors to construct phosphonoalkynes for the first time.

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Selective P−C(sp³) Bond Cleavage and Radical Alkynylation of α‐Phosphorus Alcohols by Photoredox Catalysis

Jia

Chen

2018

Chemistry A European J

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ChemInform Abstract: Base‐Catalyzed Addition of Ketones to Alkynes as a Key Step in the One‐Pot Synthesis of 1‐Formyl‐2‐pyrazolines.

et al. 2015

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An Expedient Access to γ‐Ketophosphine Chalcogenides via the Chemo‐ and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ‐Ethylenic Ketones

Artem’ev

Малышева

Белогорлова

et al. 2015

Heteroatom Chemistry

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γ‐Ketophosphine chalcogenides, precursors for plethora of novel functionalized phosphine chalcogenides and phosphines, are synthesized by chemo‐ and regioselective addition of secondary phosphine chalcogenides to β,γ‐ethylenic ketones under catalyst‐ and solvent‐free conditions (80–100°C, 8–70 h) in excellent yields. The straightforward superbase‐catalyzed synthesis of starting β,γ‐ethylenic ketones from ketones and acetylenes insures the expedient access to the target γ‐ketophosphine chalcogenides.

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Base-Catalyzed Addition of Ketones to Alkynes as a Key Step in the One-Pot Synthesis of 1-Formyl-2-pyrazolines

Abstract: The reaction of ketones with alkynes in the presence of potassium tert-butoxide and dimethylsulfoxide followed by the treatment of the reaction mixture with hydrazine hydrate and formic acid leads to 2-pyrazoline-1-carbaldehydes in up to 81% yield.

Cited by 9 publications

References 6 publications

Selective P−C(sp³) Bond Cleavage and Radical Alkynylation of α‐Phosphorus Alcohols by Photoredox Catalysis

Selective P−C(sp³) Bond Cleavage and Radical Alkynylation of α‐Phosphorus Alcohols by Photoredox Catalysis

ChemInform Abstract: Base‐Catalyzed Addition of Ketones to Alkynes as a Key Step in the One‐Pot Synthesis of 1‐Formyl‐2‐pyrazolines.

An Expedient Access to γ‐Ketophosphine Chalcogenides via the Chemo‐ and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ‐Ethylenic Ketones

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Base-Catalyzed Addition of Ketones to Alkynes as a Key Step in the One-Pot Synthesis of 1-Formyl-2-pyrazolines

Abstract: The reaction of ketones with alkynes in the presence of potassium tert-butoxide and dimethylsulfoxide followed by the treatment of the reaction mixture with hydrazine hydrate and formic acid leads to 2-pyrazoline-1-carbaldehydes in up to 81% yield.

Cited by 9 publications

References 6 publications

Selective P−C(sp3) Bond Cleavage and Radical Alkynylation of α‐Phosphorus Alcohols by Photoredox Catalysis

Selective P−C(sp3) Bond Cleavage and Radical Alkynylation of α‐Phosphorus Alcohols by Photoredox Catalysis

ChemInform Abstract: Base‐Catalyzed Addition of Ketones to Alkynes as a Key Step in the One‐Pot Synthesis of 1‐Formyl‐2‐pyrazolines.

An Expedient Access to γ‐Ketophosphine Chalcogenides via the Chemo‐ and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ‐Ethylenic Ketones

Contact Info

Product

Resources

About

Selective P−C(sp³) Bond Cleavage and Radical Alkynylation of α‐Phosphorus Alcohols by Photoredox Catalysis

Selective P−C(sp³) Bond Cleavage and Radical Alkynylation of α‐Phosphorus Alcohols by Photoredox Catalysis