New Synthetic Technology for the Rapid Construction of Novel Heterocycles. Part 1. The Reaction of Dess-Martin Periodinane with Anilides and Related Compounds.

The unusual behavior of hypervalent iodine reagents, Dess – Martin periodinane and IBX, with an array of anilides leads to the formation of complex heterocycles in only one synthetic operation (see scheme). Furthermore, the substrates for these transformations are available in one step from readily available commercial building blocks. The mechanism by which these periodinanes interact with anilides is also explored. This exciting new class of chemical reactions was discovered during the course of the total synthesis of the CP molecules and leads to compounds which are relevant to chemical biology investigations and pharmaceutical research.