Abstract: N, O-Disubstituted hydroxylamines (R(1)NHOR2 or NODHA), unlike the O-monosubstituted derivatives, have received little attention so far. However, they have recently become important as intermediates for synthesizing complex nitrogen-containing compounds, especially natural products and their analogues. The formation of NODHA by stereoselective reduction, nucleophile and radical additions provides access to acyclic, carbo- and heterocyclic amines, many of which are naturally occurring and biologically active. New methods developed for. the acylation of N, O-dimethylhydroxylamine and polymer-bound N, O-disubstituted hydroxylamines are an improvement on the Weinreb amide methodology and provide convenient routes to complex aldehydes and ketones as well as hydroxamic acids. Reductive and base-induced cleavage of the N-O bond of N, O-disubstituted hydroxylamines makes them valuable intermediates for preparing highly functionalized amines. Methods for the synthesis of bis(alkoxyamines) and their use as precursors to alkoxy-substituted heterocycles are described. Their bisnitroso derivatives on intramolecular cyclization provide an entry to hitherto unknown 4,5-dihydro-1,2,3-triazole 2-oxides. Finally, the review describes recent studies of naturally occurring and biologically active N, O-disubstituted hydroxylamines.

Cite: Khlestkin V. , Mazhukin D.
Recent advances in the application of N,O-dialkylhydroxylamines in organic chemistry
Current Organic Chemistry. 2003. V.7. N10. P.967-993. DOI: 10.2174/1385272033486639 WOS Scopus

Dates:

Published print:

Jul 1, 2003

Identifiers:

Web of science	WOS:000183381300004
Scopus	2-s2.0-0037789567
OpenAlex	W2952181246

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