Direct observation of electron transfer between phenothiazines and 1,2-dioxetanes

Adam, Waldemar; Hückmann, Sabine; Vargas, Franklin

doi:10.1016/s0040-4039(01)93881-x

Tetrahedron Letters

1989

DOI: 10.1016/s0040-4039(01)93881-x

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Direct observation of electron transfer between phenothiazines and 1,2-dioxetanes

Waldemar Adam

Sabine Hückmann

Franklin Vargas

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Cited by 8 publications

(1 citation statement)

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“…On the contrary, the milder chromium based oxidizing agents like CrtVpyridine (20), resulted in sulfoxide formation. Ozone (21), electrochemical methods (22), tetramethyl oxirane (23) or perfluoroalkyloxaziridines (24) were also used for oxidizing phenothiazines to sulfoxides.…”

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confidence: 99%

Selective Oxidaton Methods for Preparation of N-Alkylphenothiazine Sulfoxides and Sulfones

Toşa

Paiz

Majdik

et al. 2001

Heterocyclic Communications

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Efficient and selective oxidation methods for preparation of jV-alkylphenothiazine sulfoxides 2a-h and sulfones 3a-h starting from jV-alkylphenothiazines la-h are described.In the metabolism of the phenothiazine-based drugs often occuring metabolites are the corresponding sulfoxides, 7-hydroxylated derivatives or even sulfones (1-4).Phenothiazines have been oxidized by various oxidizing agents. Most frequently H2O2 in various solvents has been used for S-oxidation (1). In ethanol (5) or in ethanol-acetone mixture (6), H2O2 produced phenothiazine-5-oxides. Sulfones were usually formed by H2O2/ACOH (7) which generates in situ peracetic acid. Similarly, oxidation with organic peracids, such as m-chloroperoxybenzoic acid (8), provided sulfones.Sulfone formation was also achieved with sodium perborate (9) or NaOCl (10). Sulfoxide formation by peracid systems was only reported for ammonium persulfate (11) or H202/oxalic acid (12). Transformation of phenothiazine derivatives into sulfoxides was achieved by several inorganic nitrogen oxides. Phenothiazines substituted with electron withdrawing groups were converted to sulfoxides by nitric acid (1). Sulfoxides were obtained by using nitrous acid generated in situ from NaN02 by acids like AcOH (13) or aqueous HCl (14).Phenothiazines were converted into sulfoxides by nitrogen dioxide/02 (15) or N0 ( " ) BF 4 (+) /02(16). Heavy metalbased systems were also used for ^-oxidation of phenothiazines. KMnO^O (17), Et 3 PhN (+> Mn04 ( " ) in organic

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mentioning

confidence: 99%

Selective Oxidaton Methods for Preparation of N-Alkylphenothiazine Sulfoxides and Sulfones

Toşa

Paiz

Majdik

et al. 2001

Heterocyclic Communications

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Decomposition of dioxetane induced by electron transfer from a photoexcited lanthanide ion

et al. 1993

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The oxidation of cyclic sulfides by tetramethyldioxetane and the isobutanal/O 2 /peroxidase system: Oxygen transfer versus electron transfer

Bechara

Catalani

1995

Free Radical Biology and Medicine

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Direct observation of electron transfer between phenothiazines and 1,2-dioxetanes

Cited by 8 publications

References 14 publications

Selective Oxidaton Methods for Preparation of N-Alkylphenothiazine Sulfoxides and Sulfones

Selective Oxidaton Methods for Preparation of N-Alkylphenothiazine Sulfoxides and Sulfones

Decomposition of dioxetane induced by electron transfer from a photoexcited lanthanide ion

The oxidation of cyclic sulfides by tetramethyldioxetane and the isobutanal/O 2 /peroxidase system: Oxygen transfer versus electron transfer

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