One-pot, three-component, domino Heck-aza-Michael approach to libraries of functionalized 1,1-dioxido-1,2-benzisothiazoline-3-acetic acids.
A sequential three-component synthesis of functionalized benzisothiazoline-3-acetic acid 1,1-dioxides utilizing a domino Heck-aza-Michael pathway is reported. This one-pot procedure rapidly assembles functionalized benzylsulfonamides, which undergo a palladium-catalyzed, domino, Heck-aza-Michael transformation in an experimentally straightforward manner. This attractive protocol has been utilized to synthesize three combinatorial sublibraries (I-III) comprising a total of 95 compounds in high purities (> or =95% for 75 compounds), yield and quantities.
Rolfe
Alan
A
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA.
Young
Kyle
K
Volp
Kelly
K
Schoenen
Frank
F
Neuenswander
Benjamin
B
Lushington
Gerald H
GH
Hanson
Paul R
PR
D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000191:economics / Q000379:methods*; D010087:Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry*
D000085:Acetates; D010087:Oxides; D054852:Small Molecule Libraries; D013844:Thiazoles; C015699:1,2-benzisothiazoline-3-one