Solid-Phase Synthesis of Biologically Interesting Compounds Containing Hydroxamic Acid Moiety

Abstract

Chemical strategies developed for the solid-phase synthesis of hydroxamates are divided into four groups: (i) the traditional synthesis of hydroxamates via cleavage of resin-bound esters by hydroxylamine and its derivatives, (ii) introduction of hydroxamic acid moiety on the resin-bound precursor, (iii) transformation of polymer-supported hydroxylamine, attached to a solid supported linker either by oxygen (O-linking strategy) or by nitrogen (N-linking strategy), and (iv) synthesis of N-alkyl hydroxamates. The scope and limitation of individual approaches are discussed.

Mining the Chemical Space: Application of 2/4-Nitrobenzenesulfonamides in Solid-Phase Synthesis

“…A similar approach developed a set of novel benzyloxy, benzylamine, and benzhydrylamine linkers. ,, Whereas linkers 48 and 49 have been designed for synthesis of N -alkyl and N -aryl hydroxamates (as discussed in subchapter , Scheme ), linkers 50 and 51 have been developed as an alternative to backbone amide linkers (BALs) Scheme depicts the individual types of linkers along with a representative example of the synthetic procedure.…”

Polymer-Supported N-Derivatized, O-Linked Hydroxylamine for Concurrent Solid-Phase Synthesis of Diverse N-Alkyl and N−H Hydroxamates

“…The current prevailing route for solid-phase synthesis of hydroxamates is through immobilized hydroxylamine. Typically, the hydroxylamine derivatives are attached to a solid support via the oxygen (Scheme ), although attachment through the nitrogen has also been utilized . The most common preparative route to O-immobilized hydroxylamine is by the reaction of N- hydroxyphthalimide with Wang or Sasrin resins under Mitsunobu conditions. − Alternatively, hydroxyl resins can be converted to mesylate resins and reacted with N- hydroxyphthalimide, or trityl chloride resins can be directly reacted with either N- hydroxyphthalimide − or N- Fmoc hydroxylamine .…”