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)

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 ( 1 H-NMR) spectroscopy. © 2012 Akadémiai Kiadó.