Accessing Stereochemically Rich Sultams via Microwave-assisted, Continuous-flow Organic Synthesis (MACOS) Scale-out

Michael G. Organ; Paul R. Hanson; Alan Rolfe; Thiwanka B. Samarakoon; Farman Ullah

doi:10.1556/jfchem.2011.00008

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Journal of Flow Chemistry

Volume/Issue:: Volume 1: Issue 1

Accessing Stereochemically Rich Sultams via Microwave-assisted, Continuous-flow Organic Synthesis (MACOS) Scale-out

Authors:

Michael G. Organ

Michael G. Organ Department 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. Hanson

Paul R. Hanson 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
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA

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Alan Rolfe

Alan Rolfe 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
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA

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Thiwanka B. Samarakoon

Thiwanka B. Samarakoon 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
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA

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, and

Farman Ullah

Farman Ullah Department 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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Pages:: 32–39

Online Publication Date:: 29 Feb 2012

Publication Date:: 29 Feb 2012

Article Category:: Research Article

DOI:: https://doi.org/10.1556/jfchem.2011.00008

Keywords:: microwave-assisted; continuous-flow organic synthesis (MACOS); Sultam; SNAr; diversity-oriented synthesis (DOS); high-throughput screening (HTS)

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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/S_NAr cyclization protocol. Diversification of these sultam scaffolds was attained via a microwave-assisted intermolecular S_NAr 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 A Journal of the Flow Chemistry Society

Print ISSN:: 2062-249X

Online ISSN:: 2063-0212

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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)