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Heterocycles from Hydroxylamines and Hydroxamic Acids

Hydroxylamines, Oximes and Hydroxamic Acids (2010)

  1. Martins Katkevics,
  2. Tatyana Kukosha,
  3. Edmunds Lukevics

Published Online: 15 SEP 2010

DOI: 10.1002/9780470682531.pat0502

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Katkevics, M., Kukosha, T. and Lukevics, E. 2010. Heterocycles from Hydroxylamines and Hydroxamic Acids. Patai's Chemistry of Functional Groups. .

Author Information

  1. Latvian Institute of Organic Synthesis, Riga, Latvia

Publication History

  1. Published Online: 15 SEP 2010

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.

Keywords:

  • hydroxylamines;
  • hydroxamic acids;
  • heterocycles;
  • lactams;
  • nitrones;
  • nitroso compounds;
  • acylnitrenium ions;
  • cycloaddition;
  • electrophilic aromatic cylization;
  • hetero-Cope rearrangement