Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 7, Issue 3, Pages 589-597Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b816608k
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Funding
- GlaxoSmithKline
- University of Manchester
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The reaction of thiols with glyoxamides provides a convenient method for the generation of thionium ions and the initiation of Pummerer-type reactions. When the glyoxamides contain tethered aromatic nucleophiles, N-heterocycles are formed by a thionium ion cyclisation. The scope and mechanism of the connective Pummerer-type process has been investigated using a range of thiols, Lewis acids and both mono- and bis-glyoxamides. The utility of the process has been illustrated in a synthesis of the indoloquinoline natural product, neocryptolepine.
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