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)

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 utiliz...

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Bibliographic Details
Published in:Journal of flow chemistry 2012-12, Vol.2 (4), p.118-123
Main Authors: Ullah, Farman, Zang, Qin, Javed, Salim, Zhou, Aihua, Knudtson, Christopher A., Bi, Danse, Hanson, Paul R., Organ, Michael G.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Green Chemistry
Industrial Chemistry/Chemical Engineering
Inorganic Chemistry
Nanochemistry
Organic Chemistry
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Summary: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 ( 1 H-NMR) spectroscopy.
ISSN:2062-249X
2063-0212
DOI:10.1556/JFC-D-12-00015