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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Published in | Tetrahedron letters Vol. 57; no. 21; pp. 2215 - 2218 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
25.05.2016
Elsevier |
Subjects | |
Online Access | Get full text |
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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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2016.03.065 |