44 research outputs found

    Synthesis of Fused Pyran Derivatives via Visible-Light-Induced Cascade Cyclization of 1,7-Enynes with Acyl Chlorides

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    A photocatalytic cascade cyclization of 1,7-enynes with acyl chlorides has been established. This method offers an operationally simple access to diverse fused pyran derivatives with a broad substrate scope in high yields from simple acyl chlorides via an acyl radical intermediate

    Synthesis of Fused Pyran Derivatives via Visible-Light-Induced Cascade Cyclization of 1,7-Enynes with Acyl Chlorides

    No full text
    A photocatalytic cascade cyclization of 1,7-enynes with acyl chlorides has been established. This method offers an operationally simple access to diverse fused pyran derivatives with a broad substrate scope in high yields from simple acyl chlorides via an acyl radical intermediate

    α‑Oxo-γ-Butyrolactam, <i>N</i>‑Containing Pronucleophile in Organocatalytic One-Pot Assembly of Butyrolactam-Fused Indoloquinolizidines

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    The ambident reactivity of α-oxo-γ-butyrolactam has been explored in an organocatalytic one-pot Michael/Pictet–Spengler sequence. The synthetically interesting and medicinally important pentacyclic butyrolactam-fused indoloquinolizidines can be efficiently constructed in a highly stereocontrolled manner. Importantly, the chemistry described herein provides a general catalytic method for the enantioselective synthesis of butyrolactam-incorporated chemical entities

    α‑Oxo-γ-Butyrolactam, <i>N</i>‑Containing Pronucleophile in Organocatalytic One-Pot Assembly of Butyrolactam-Fused Indoloquinolizidines

    No full text
    The ambident reactivity of α-oxo-γ-butyrolactam has been explored in an organocatalytic one-pot Michael/Pictet–Spengler sequence. The synthetically interesting and medicinally important pentacyclic butyrolactam-fused indoloquinolizidines can be efficiently constructed in a highly stereocontrolled manner. Importantly, the chemistry described herein provides a general catalytic method for the enantioselective synthesis of butyrolactam-incorporated chemical entities

    Visible-Light-Induced Aza-Pinacol Rearrangement: Ring Expansion of Alkylidenecyclopropanes

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    A novel visible-light-induced aza-pinacol rearrangement was developed for the first time. In this approach, the addition of the N-centered radical to the CC bond of alkylidenecyclopropanes delivers a variety of cyclobutanimines and γ-butyrolactones, with all-carbon quaternary centers via the ring expansion of the cyclopropyl group, in moderate to good yields under mild reaction conditions

    Visible-Light-Induced Alkoxypyridylation of Alkenes Using N‑Alkoxypyridinium Salts as Bifunctional Reagents

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    Considering the ubiquitous presence of pyridine moieties in pharmaceutical compounds, it holds immense value to develop practical and straightforward methodologies for accessing heterocyclic aromatic hydrocarbons. In recent years, N-alkoxypyridinium salts have emerged as convenient radical precursors, enabling the generation of the corresponding alkoxy radicals and pyridine through single-electron transfer. Herein, we present the first report on visible-light-mediated intermolecular alkoxypyridylation of alkenes employing N-alkoxylpyridinium salts as bifunctional reagents with an exceptionally low catalyst loading (0.5 mol %)

    TiCl<sub>4</sub> Promoted Formal [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters with Azides: Synthesis of Highly Functionalized Triazinines and Azetidines

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    A TiCl<sub>4</sub> promoted formal [3 + 3] cycloaddition of cyclopropane 1,1-diesters with azides has been developed for the synthesis of highly functionalized triazinines. Both stoichiometric and substoichiometric versions of this reaction were accomplished dependent on the choice of solvent. It is noteworthy that the corresponding products could be easily converted to biologically important azetidines by simple thermolysis

    3,4,5-Trimethylphenol and Lewis Acid Dual-Catalyzed Cascade Ring-Opening/Cyclization: Direct Synthesis of Naphthalenes

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    A 3,4,5-trimethylphenol and Lewis acid dual-catalyzed cascade reaction of donor–acceptor (D–A) cyclopropanes via ring-opening and cyclization is developed. In this reaction, a phenolic compound was used as a covalent catalyst for the first time. Additionally, control experiments proved that 3,4,5-trimethylphenol completed the catalytic cycle by accomplishing the C–C bond cleavage. Using this strategy, a wide variety of substituted naphthalenes has been synthesized from D–A cyclopropanes in moderate to high yields under mild conditions

    Rh(II) Catalyzed High Order Cycloadditions of 8‑Azaheptafulvenes with <i>N</i>‑Sulfonyl 1,2,3-Triazloes or α‑Oxo Diazocompounds

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    A novel strategy was developed for the application of Rh carbenes generated from readily accessible <i>N</i>-sulfonyl 1,2,3,-triazoles or diazocompouds in the high order cycloadditions, which offered an efficient route to a variety of N-containing medium-sized rings. The process provided a wide range of cyclo­hepta­[<i>b</i>]­pyrazine and cyclo­hepta­[<i>b</i>]­pyrrolone derivatives with high yields
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