2,1-Benzisothiazolium salts react with several stabilized carbanions to give products that are derived by attack at the carbon atom of the heterocyclic ring.
Several 3-aminothiophene-2-carboxylic ester derivatives are made by reaction of potassium 3-ethoxy-3-oxopropanoate with isothiazolium salts or by reaction with 2-ethoxy-2-oxoethylidenedimethylsulfurane. In the latter case deaminated products are also isolated. These products are consistent with initial nucleophilic attack on the sulfur atom of the isothiazolium salt. In one case a pyrrole derivative is formed by a novel rearrangement of an intermediate aziridine derivative. Some further derivatives of 3-benzylaminobenzo[b]thiophene are described.
Beim Behandeln des Benzothiazoliumsalzes (Ia) mit Triethylamin und Aufarbeiten des Produkts mit HCl/HZO entstehen infolge einer Dismutation des durch einen nucleophilen Angriff des Wassers auf den Heteroring von (Ia) gebildeten Reaktionsprodukts der Aldehyd (II) und das Thion (III), wobei ein S‐Atom zwischen den Molekülen transferiert wird.
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