Automated synthesis of a 184-member library of thiadiazepan-1,1-dioxide-4-ones
Erik Fenster1, Toby R Long, Qin Zang
1Center for Chemical Methodologies and Library Development at the University of Kansas, Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States.
Abstract:
The construction of a 225-member (3 × 5 × 15) library of thiadiazepan-1,1-dioxide-4-ones was performed on a Chemspeed Accelerator (SLT-100) automated parallel synthesis platform, culminating in the successful preparation of 184/225 sultams. Three sultam core scaffolds were prepared based upon the utilization of an aza-Michael reaction on a multifunctional vinyl sulfonamide linchpin. The library exploits peripheral diversity in the form of a sequential, two-step [3 + 2] Huisgen cycloaddition/Pd-catalyzed Suzuki-Miyaura coupling sequence.
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