Peroxide-mediated oxidative coupling of primary alcohols and disulfides: Synthesis of 2-substituted benzothiazoles

[Display omitted] •Benzothiazoles were efficiently prepared starting from disulfides and primary alcohols.•2-Alkylbenzothiazoles were prepared from primary alcohols using DTBP as oxidant.•Bis(o-aminophenyl) disulfides were converted to 2-arylbenzothiazoles.•2-Arylbenzothiazoles were prepared from be...

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Published inTetrahedron letters Vol. 60; no. 24; pp. 1587 - 1591
Main Authors Padilha, Nathalia B., Penteado, Filipe, Salomão, Maria C., Lopes, Eric F., Bettanin, Luana, Hartwig, Daniela, Jacob, Raquel G., Lenardão, Eder J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.06.2019
Elsevier
Subjects
Benzothiazoles
C-S bond formation
Chemistry
Chemistry, Organic
Disulfides
Oxidative coupling
Physical Sciences
Science & Technology
Oxidative coupling
C-S bond formation
Disulfides
Benzothiazoles
ALZHEIMERS-DISEASE
ANTITUMOR BENZOTHIAZOLES
PHOTOPHYSICAL PROPERTIES
THIOFLAVINE-T INTERACTION
CATALYZED ARYLATION
H BOND ADJACENT
PROMOTED SYNTHESIS
AMYLOID-BETA
N-ALKYLATION
BIOLOGICAL-PROPERTIES
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Summary:[Display omitted] •Benzothiazoles were efficiently prepared starting from disulfides and primary alcohols.•2-Alkylbenzothiazoles were prepared from primary alcohols using DTBP as oxidant.•Bis(o-aminophenyl) disulfides were converted to 2-arylbenzothiazoles.•2-Arylbenzothiazoles were prepared from benzylic alcohols in the presence of DTBP. A peroxide-mediated protocol for the synthesis of 2-substituted benzothiazoles was developed, starting from bis(o-aminophenyl) disulfides and primary alcohols. Eleven differently 2-substituted benzothiazoles were prepared in moderate to excellent yields using di-tert-butyl peroxide (DTBP) as an oxidant.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.05.021