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Synthesis 2011(17): 2743-2750  
DOI: 10.1055/s-0030-1260112
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Application of a Double Aza-Michael Reaction in a ‘Click, Click, Cy-Click’ Strategy: From Bench to Flow

Qin Zanga, Salim Javeda, Farman Ullahb, Aihua Zhoua, Christopher A. Knudtsona, Danse Bia, Fatima Z. Bashac, Michael G. Organ*b, Paul R. Hanson*a
a Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582 , and the 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
Fax: +1(785)8645396; e-Mail: phanson@ku.edu;
b Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada
Fax: +1(416)7365936; e-Mail: organ@yorku.ca;
c H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological SciencesUniversity of Karachi, Pakistan
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Publication History

Received 18 March 2011
Publication Date:
14 July 2011 (online)

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Abstract

The development of a ‘click, click, cy-click’ process utilizing a double aza-Michael reaction to generate functionalized 1,2,5-thiadiazepane 1,1-dioxides is reported. Optimization in flow, followed by scale out of the inter-/intramolecular double aza-Michael addition has also been realized using a microwave-assisted, continuous flow organic synthesis platform (MACOS). In addition, a facile one-pot, sequential strategy employing in situ Huisgen cycloaddition post-double aza-Michael has been accomplished, and is applicable to library synthesis.

Key words

double-aza-Michael - click - MACOS - flow - 1,2,5-thiadiazepane 1,1-dioxides