One-pot, three-component, domino Heck-aza-Michael approach to libraries of functionalized 1,1-dioxido-1,2-benzisothiazoline-3-acetic acids

J Comb Chem. 2009 Jul-Aug;11(4):732-8. doi: 10.1021/cc900025e.

Abstract

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemical synthesis*
  • Acetates / chemistry
  • Combinatorial Chemistry Techniques / economics
  • Combinatorial Chemistry Techniques / methods*
  • Oxides / chemical synthesis*
  • Oxides / chemistry
  • Small Molecule Libraries / chemical synthesis*
  • Small Molecule Libraries / chemistry
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry*

Substances

  • Acetates
  • Oxides
  • Small Molecule Libraries
  • Thiazoles
  • 1,2-benzisothiazoline-3-one