1130682-58-4Relevant articles and documents
Formation of N-heterocycles by the reaction of thiols with glyoxamides: Exploring a connective Pummerer-type cyclisation
Miller, Marc,Vogel, Johannes C.,Tsang, William,Merrit, Andrew,Procter, David J.
experimental part, p. 589 - 597 (2009/07/18)
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. The Royal Society of Chemistry 2009.