Heterocycles from Hydroxylamines and Hydroxamic Acids

Abstract

Hydroxylamines and hydroxamic acids are polyfunctional organic molecules and several reactive intermediates can be generated from them, therefore they have found broad application in the synthesis of various nitrogen and oxygen containing heterocycles by means of nulceophilic substitution or addition, electrophilic intramolecular aromatic substitution, as well as [2+4] and [3+2] cycloaddition reactions. This chapter surveys synthesis of heterocycles from the title compounds highlighting some distinguished reaction mechanism aspects, regio‐ and stereo selectivity issues and experimental details. It is arranged according to the size and type of heterocycles that allows fast but also explanatory insight into synthesis of the particular cycles.

Synthesis of small and medium size monocyclic hydroxamic acids (Review)*

“…7-Membered CHA, as well as exochelin MN, a 6-membered CHA, are among commonly found siderophores (Fe 3+ -binding ligands) [5] (Fig. 2 Some of the methods for cyclic hydroxamic acid synthesis starting from hydroxylamines or hydroxamic acids have been reviewed in a recent book [6]. We have organized this review in the following way: we start with specific synthetic methods for each of the 4-6 membered heterocycles and then turn to methods for the formation of CHA of several cycle sizes.…”