Nickel Peroxide Dehydrogenation of Oxygen-, Sulfur-, and Nitrogen-Containing Heterocycles

David L. Evans, David K. Minster, Ulrich Jordis, Sidney Hecht, Arthur L. Mazzu, A. I. Meyers

Research output: Contribution to journalArticle

129 Citations (Scopus)

Abstract

Twenty-seven partially reduced O-, S-, and N-containing heterocvcles have been oxidized by the use of nickel peroxide. Of particular interest were the conversions of several oxazolines to the corresponding oxazoles, a conversion apparently without precedent in the chemical literature, and the efficient oxidation of thiazolines to thiazoles. Since Ni02 can effect thiazoline dehydrogenations in the presence of other functionalities, as may be judged by the successful oxidation of phleomycin A2 to bleomycin A2, the oxidant should be of utility for the preparation of natural products containing thiazoles.

Original languageEnglish (US)
Pages (from-to)497-501
Number of pages5
JournalJournal of Organic Chemistry
Volume44
Issue number4
DOIs
StatePublished - 1979
Externally publishedYes

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Thiazoles
Peroxides
Dehydrogenation
Nickel
Sulfur
Phleomycins
Nitrogen
Oxazoles
Oxygen
Oxidation
Bleomycin
Biological Products
Oxidants

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Nickel Peroxide Dehydrogenation of Oxygen-, Sulfur-, and Nitrogen-Containing Heterocycles. / Evans, David L.; Minster, David K.; Jordis, Ulrich; Hecht, Sidney; Mazzu, Arthur L.; Meyers, A. I.

In: Journal of Organic Chemistry, Vol. 44, No. 4, 1979, p. 497-501.

Research output: Contribution to journalArticle

Evans, David L. ; Minster, David K. ; Jordis, Ulrich ; Hecht, Sidney ; Mazzu, Arthur L. ; Meyers, A. I. / Nickel Peroxide Dehydrogenation of Oxygen-, Sulfur-, and Nitrogen-Containing Heterocycles. In: Journal of Organic Chemistry. 1979 ; Vol. 44, No. 4. pp. 497-501.
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