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

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Issue Date
2012-07-04Author
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
Metadata
Show full item recordAbstract
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%).
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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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