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Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)
dc.contributor.author | Ullah, Farman | |
dc.contributor.author | Zang, Qin | |
dc.contributor.author | Javed, Salim | |
dc.contributor.author | Porubsky, Patrick R. | |
dc.contributor.author | Neuenswander, Benjamin | |
dc.contributor.author | Lushington, Gerald H. | |
dc.contributor.author | Hanson, Paul R. | |
dc.contributor.author | Organ, Michael G. | |
dc.date.accessioned | 2017-01-05T18:28:10Z | |
dc.date.available | 2017-01-05T18:28:10Z | |
dc.date.issued | 2012-07-04 | |
dc.identifier.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. | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/22461 | |
dc.description.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%). | en_US |
dc.publisher | Thieme Publishing | en_US |
dc.relation.isversionof | https://www.thieme-connect.de/products/ejournals/html/10.1055/s-0031-1289791 | en_US |
dc.subject | MACOS | en_US |
dc.subject | Continuous flow | en_US |
dc.subject | Sultams | en_US |
dc.subject | Heck reaction | en_US |
dc.subject | Aza-Michael addition | en_US |
dc.subject | Isoindolines | en_US |
dc.title | Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS) | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Javed, Salim | |
kusw.kudepartment | Chemistry | en_US |
dc.identifier.doi | 10.1055/s-0031-1289791 | en_US |
kusw.oaversion | Scholarly/refereed, publisher version | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.rights.accessrights | openAccess |