Multicapillary Flow Reactor: Synthesis of 1,2,5-Thiadiazepane 1,1-Dioxide Library Utilizing One-Pot Elimination and Inter-/Intramolecular Double aza-Michael Addition Via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)

Farman Ullah; Qin Zang; Salim Javed; Aihua Zhou; Christopher A. Knudtson; Danse Bi; Paul R. Hanson; Michael G. Organ

doi:10.1556/jfc-d-12-00015

Journal of Flow Chemistry

Volume/Issue:: Volume 2: Issue 4

Multicapillary Flow Reactor: Synthesis of 1,2,5-Thiadiazepane 1,1-Dioxide Library Utilizing One-Pot Elimination and Inter-/Intramolecular Double aza-Michael Addition Via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)

Authors:

Farman Ullah

Farman Ullah Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada
Center for Chemical Methodologies and Library Development at the University of Kansas (KU-CMLD), 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, KS, 66047-3761, USA

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Qin Zang

Qin Zang Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada
Center for Chemical Methodologies and Library Development at the University of Kansas (KU-CMLD), 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, KS, 66047-3761, USA

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Salim Javed

Salim Javed Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS, 66045-7582, USA
Center for Chemical Methodologies and Library Development at the University of Kansas (KU-CMLD), 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, KS, 66047-3761, USA

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Aihua Zhou

Aihua Zhou Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS, 66045-7582, USA
Center for Chemical Methodologies and Library Development at the University of Kansas (KU-CMLD), 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, KS, 66047-3761, USA

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Christopher A. Knudtson

Christopher A. Knudtson Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS, 66045-7582, USA
Center for Chemical Methodologies and Library Development at the University of Kansas (KU-CMLD), 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, KS, 66047-3761, USA

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Danse Bi

Danse Bi Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS, 66045-7582, USA
Center for Chemical Methodologies and Library Development at the University of Kansas (KU-CMLD), 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, KS, 66047-3761, USA

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Paul R. Hanson

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

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Michael G. Organ

Michael G. Organ Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada
Center for Chemical Methodologies and Library Development at the University of Kansas (KU-CMLD), 2034 Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, KS, 66047-3761, USA

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Pages:: 118–123

Online Publication Date:: 13 Dec 2012

Publication Date:: 13 Dec 2012

Article Category:: Research Article

DOI:: https://doi.org/10.1556/jfc-d-12-00015

Keywords:: double aza-Michael; MACOS; 1,2,5-thiadiazepane 1,1-dioxide library; sultams

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Abstract

A microwave-assisted, continuous-flow organic synthesis (MACOS) protocol for the synthesis of functionalized 1,2,5-thiadiazepane 1,1-dioxide library, utilizing a one-pot elimination and inter-/intramolecular double aza-Michael addition strategy is reported. The optimized protocol in MACOS was utilized for scale-out and further extended for library production using a multicapillary flow reactor. A 50-member library of 1,2,5-thiadiazepane 1,1-dioxides was prepared on a 100- to 300-mg scale with overall yields between 50 and 80% and over 90 % purity determined by proton nuclear magnetic resonance (¹H-NMR) spectroscopy.

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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)