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    Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)

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    Issue Date
    2012-07-04
    Author
    Ullah, Farman
    Zang, Qin
    Javed, Salim
    Porubsky, Patrick R.
    Neuenswander, Benjamin
    Lushington, Gerald H.
    Hanson, Paul R.
    Organ, Michael G.
    Publisher
    Thieme Publishing
    Type
    Article
    Article Version
    Scholarly/refereed, publisher version
    Published Version
    https://www.thieme-connect.de/products/ejournals/html/10.1055/s-0031-1289791
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    Abstract
    A microwave-assisted, continuous-flow organic synthesis (MACOS) protocol for the synthesis of an isoindoline-annulated, tricyclic sultam library, utilizing a Heck–aza-Michael (HaM) strategy, is reported. This sequence involves a Heck reaction on vinylsulfonamides with batch microwave heating followed by a one-pot, sequential intramolecular aza-Michael cyclization/Boc-deprotection using MACOS. Subsequent cyclization with either 1,1′-carbonyldiimidazole or chloromethyl pivalate using MACOS provided an array of tricyclic sultams. This efficient three-step protocol requires only a few hours to produce the target sultams starting from simple starting materials. Using this strategy, a 38-member library of isoindoline-annulated sultams was generated in good to excellent overall yields (53–87%).
    URI
    http://hdl.handle.net/1808/22461
    DOI
    https://doi.org/10.1055/s-0031-1289791
    Collections
    • Chemistry Scholarly Works [601]
    Citation
    Hanson, Paul, Michael Organ, Farman Ullah, Qin Zang, Salim Javed, Patrick Porubsky, Benjamin Neuenswander, and Gerald Lushington. "Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)." Synthesis 44.16 (2012): 2547-554.

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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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