26 research outputs found

    Divergent Synthesis of Benzene Derivatives: Brønsted Acid Catalyzed and Iodine-Promoted Tandem Cyclization of 5,2-Enyn-1-ones

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    Highly substituted benzene derivatives, including alkoxy-, iodoalkoxy-, and diiodo-substituted benzenes, can be selectively synthesized via Brønsted acid catalyzed and iodine-promoted tandem carbocyclization respectively. This reaction involved a direct process for C–C bond formation from 5,2-enyn-1-ones, and different reaction systems (Brønsted acids/electrophiles with solvents) afforded different substituted benzenes. Furthermore, the halogenated moiety and alkoxy group can be readily introduced into the benzene in a position which has not been easily obtained previously

    Gold-Catalyzed Tandem [3,3]-Propargyl Ester Rearrangement Leading to (<i>E</i>)‑1<i>H</i>‑Inden-1-ones

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    An efficient method for the synthesis of (<i>E</i>)-1<i>H</i>-inden-1-ones using gold-catalyzed tandem [3,3]-propargyl ester rearrangement followed by Michael addition under mild reaction conditions has been developed. The resulting products are important frameworks found in numerous natural products and pharmaceutically active compounds, as well as being valuable intermediates in organic synthesis

    Gold-Catalyzed Tandem [3,3]-Propargyl Ester Rearrangement Leading to (<i>E</i>)‑1<i>H</i>‑Inden-1-ones

    No full text
    An efficient method for the synthesis of (<i>E</i>)-1<i>H</i>-inden-1-ones using gold-catalyzed tandem [3,3]-propargyl ester rearrangement followed by Michael addition under mild reaction conditions has been developed. The resulting products are important frameworks found in numerous natural products and pharmaceutically active compounds, as well as being valuable intermediates in organic synthesis

    Gold-Catalyzed Tandem [3,3]-Propargyl Ester Rearrangement Leading to (<i>E</i>)‑1<i>H</i>‑Inden-1-ones

    No full text
    An efficient method for the synthesis of (<i>E</i>)-1<i>H</i>-inden-1-ones using gold-catalyzed tandem [3,3]-propargyl ester rearrangement followed by Michael addition under mild reaction conditions has been developed. The resulting products are important frameworks found in numerous natural products and pharmaceutically active compounds, as well as being valuable intermediates in organic synthesis

    Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4‑Pyrone, 4‑Pyridone, and 3‑Pyrrolone Derivatives

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    Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

    Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4‑Pyrone, 4‑Pyridone, and 3‑Pyrrolone Derivatives

    No full text
    Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

    Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4‑Pyrone, 4‑Pyridone, and 3‑Pyrrolone Derivatives

    No full text
    Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

    Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4‑Pyrone, 4‑Pyridone, and 3‑Pyrrolone Derivatives

    No full text
    Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

    TMSCl-Mediated Synthesis of α,β-Unsaturated Amides via C–C Bond Cleavage and C–N Bond Formation of Propargyl Alcohols with Trimethylsilyl Azide

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    A new method with high efficiency for the synthesis of α,β-unsaturated amides from the easily prepared propargyl alcohols and TMSN<sub>3</sub> using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C–C bond cleavage, and C–N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents

    Copper-Catalyzed Three-Component Cyano­trifluoro­methyla­tion/Azido­trifluoro­methyla­tion and Carbo­cycli­zation of 1,6-Enynes

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    A novel three-component strategy for the cyano­trifluoro­methyla­tion/azido­trifluoro­methyla­tion and carbocyclization of 1,6-enynes is developed. The reaction proceeds smoothly under a moderate temperature by using a copper catalyst, which provides a rapid and concise access to addition–carbocyclization products. Furthermore, the products obtained can be useful building blocks in discoveries of lead compounds and other biologically active CF<sub>3</sub>-containing heterocycles
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