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.

No abstract

The reaction of a range of thiols with mono- and bis-glyoxamides derived from secondary anilines, triggers a new, connective Pummerer cyclisation process and leads to the formation of oxindoles.

No abstract

Failure to resolve the aryl olefins II, III, IV and V was reported in the preceding paper.1 Compound I, on the other hand, was resolved2 and an active form had a half-life period of 173 minutes in ra-butanol at 44°. The difference between I and