Microwave-enhanced synthesis of 2,3,6-trisubstituted pyridazines: application to four-step synthesis of gabazine (SR-95531)

Org Biomol Chem. 2010 Sep 21;8(18):4131-6. doi: 10.1039/c0ob00004c. Epub 2010 Jul 26.

Abstract

Microwave-enhanced, highly efficient protocols for the synthesis of synthetically and biologically important 2,3,6-trisubstituted pyridazine architectures have been developed by sequential amination/Suzuki coupling/alkylation reactions. This powerful strategy is an economical and highly chemoselective protocol for the synthesis of diversified pyridazines. The total synthesis of gabazine (SR-95531) has been achieved using a versatile strategy in four steps and 73% overall yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Microwaves*
  • Molecular Structure
  • Pyridazines / chemical synthesis*
  • Pyridazines / chemistry
  • Stereoisomerism

Substances

  • Pyridazines
  • gabazine