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Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)
Ullah, Farman Zang, Qin Javed, Salim Porubsky, Patrick R. Neuenswander, Benjamin Lushington, Gerald H. Hanson, Paul R. Organ, Michael G.
Ullah, Farman
Zang, Qin
Javed, Salim
Porubsky, Patrick R.
Neuenswander, Benjamin
Lushington, Gerald H.
Hanson, Paul R.
Organ, Michael G.
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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%).
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Date
2012-07-04
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Thieme Publishing
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Keywords
MACOS, Continuous flow, Sultams, Heck reaction, Aza-Michael addition, Isoindolines
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.