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DOI: 10.1055/s-0034-1380434
Synthesis of the First Representatives of Spiro-1λ6-isothiazolidine-1,1,4-triones
Publikationsverlauf
Received: 30. März 2015
Accepted after revision: 28. Mai 2015
Publikationsdatum:
25. Juni 2015 (online)
Abstract
A strategy for the construction of spiro[cycloalkane-1,3′-1′λ6-isothiazolidine]-1′,1′,4′-triones through the sulfonylation of 1-aminocyclopropane- and 1-aminocyclobutanecarboxylates with methanesulfonyl chloride followed by alkylation with methyl iodide and subsequent cyclization in the presence of potassium tert-butoxide in N,N-dimethylformamide is reported. An efficient synthesis of starting 1-aminocyclopropane- and 1-aminocyclobutanecarboxylic acids was developed. The reaction of spiro[cycloalkane-1,3′-1′λ6-isothiazolidine]-1′,1′,4′-triones with N,N-dimethylformamide dimethyl acetal (DMFDMA) gives 5′-[(Z)-(dimethylamino)methylene]spiro[cycloalkane-1,3′-1′λ6-isothiazolidine]-1′,1′,4′-triones, the structure of which was confirmed by X-ray diffraction study.
Key words
amino acids - sulfonamides - spiro compounds - cyclization - X-ray structure determinationPrimary Data
- Primary data for this article are available online at http://www.thieme-connect.com/products/ejournals/journal/10.1055/s-00000084 and can be cited using the following DOI: 10.4125/pd0069th.
- Primary Data
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