doi: 10.1556/JFC-D-12-00015.
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)
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- PMID:24244871
- PMCID: PMC3827364
- DOI: 10.1556/JFC-D-12-00015
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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 et al. J Flow Chem.2012 Dec.
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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.
Keywords: 1,2,5-thiadiazepane 1,1-dioxide library; MACOS; double aza-Michael; sultams.
Figures
1,2,5-thiadiazepane 1,1-dioxide library via MACOS
One-pot elimination and double aza-Michael (DaM) strategy in flow
Preparation of double aza-Michael precursors
Synthesis of 1,2,5-thiadiazepane 1,1-dioxide library via MACOS using multi-capillary flow reactor. (A) Schematic of the parallel, capillary multireactor system. (B) Photograph of the parallel, capillary multireactor system
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