Authors:
Michael G. OrganDepartment of Chemistry, York University, 4700 Keele Street, ON, Toronto, Canada M3J 1P3
The University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD), 2034 Becker Drive, Del Shankel Structural Biology Center, Lawrence, KS 66047-3761, USA

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Paul R. HansonThe University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD), 2034 Becker Drive, Del Shankel Structural Biology Center, Lawrence, KS 66047-3761, USA
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA

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Alan RolfeThe University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD), 2034 Becker Drive, Del Shankel Structural Biology Center, Lawrence, KS 66047-3761, USA
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA

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Thiwanka B. SamarakoonThe University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD), 2034 Becker Drive, Del Shankel Structural Biology Center, Lawrence, KS 66047-3761, USA
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA

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Farman UllahDepartment of Chemistry, York University, 4700 Keele Street, ON, Toronto, Canada M3J 1P3
The University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD), 2034 Becker Drive, Del Shankel Structural Biology Center, Lawrence, KS 66047-3761, USA

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Abstract

The generation of stereochemically rich benzothiaoxazepine-1,1´-dioxides for enrichment of high-throughput screening collections is reported. Utilizing a microwave-assisted, continuous-flow organic synthesis platform (MACOS), scale-out of core benzothiaoxazepine-1,1´-dioxide scaffolds has been achieved on multigram scale using an epoxide opening/SNAr cyclization protocol. Diversification of these sultam scaffolds was attained via a microwave-assisted intermolecular SNAr reaction with a variety of amines. Overall, a facile, two-step protocol generated a collection of benzothiaoxazepine-1,1´-dioxides possessing stereochemical complexity in rapid fashion, where all eight stereoisomers were accessed from commercially available starting materials.

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Journal of Flow Chemistry
Language English
Size A4
Year of
Foundation
2011
Volumes
per Year
1
Issues
per Year
4
Founder Áramlásos Kémiai Tudományos Társaság
Founder's
Address
H-1031 Budapest, Hungary Záhony utca 7.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 2062-249X (Print)
ISSN 2063-0212 (Online)