New methods for the selective alkylation of 3-thioxo-1,2,4-triazin-5-ones

[Display omitted] •Selective S-alkylation of a polyfunctional heterocyclic system.•Rearrangements to the corresponding N-alkylated systems using either Claisen or Pd-catalysed rearrangements.•A new acid-catalysed rearrangement leading to useful thiols. A method for regioselective alkylation of the 3...

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Bibliographic Details
Published inTetrahedron letters Vol. 57; no. 21; pp. 2215 - 2218
Main Authors Ghanim, Amany M., Knight, David W., Osman, Nermine A., Abdel-Fattah, Hanan A., Kadry, Azza M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.05.2016
Elsevier
Subjects
3-Thionyl-1,2,4-triazin-5-ones
Acid-catalysed
Chemistry
Chemistry, Organic
Claisen
Physical Sciences
Rearrangement
S-alkylation
Science & Technology
Acid-catalysed
S-alkylation
3-Thionyl-1,2,4-triazin-5-ones
Claisen
Rearrangement
3-Thiony1-1,2,4-triazin-5-ones
DESIGN
1,2,4-TRIAZINE DERIVATIVES
TRIAZINES
DISCOVERY
HYPOGLYCEMIC AGENTS
AMINO-ACIDS
BIOLOGICAL EVALUATION
THIO-CLAISEN REARRANGEMENT
INHIBITORS
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Summary:[Display omitted] •Selective S-alkylation of a polyfunctional heterocyclic system.•Rearrangements to the corresponding N-alkylated systems using either Claisen or Pd-catalysed rearrangements.•A new acid-catalysed rearrangement leading to useful thiols. A method for regioselective alkylation of the 3-thiono-1,2,4-triazinone 10 at the sulfur atom is reported. Subsequent Claisen rearrangements, triggered either thermally or using a palladium catalyst, deliver N-alkylated products 13, while acid-catalysed rearrangements of examples where a tertiary carbenium ion can be generated, result in the formation of N-thioalkyl derivatives.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.03.065