Intramolecular electrophilic cyclization of functional derivatives of unsaturated Compounds: I. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones from cinnamylacetamides and arylsulfenyl chlorides View Full Text


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Article Info

DATE

2011-08

AUTHORS

A. I. Vas’kevich, N. M. Tsizorik, E. B. Rusanov, V. I. Stanitets, M. V. Vovk

ABSTRACT

Sterically nonhindered N-alkyl(aryl)amides of cinnamylacetic acid in the reaction with phenyl(4-tolyl)sulfenyl chlorides in acetic acid in the presence of lithium perchlorate undergo a selective cyclization into 5-arylsulfanyl-6-phenylpiperidin-2-ones. Under similar conditions the reaction with arylsulfenyl chlorides of amides containing bulky substituents at the nitrogen atom resulted in 5-arylsulfanyl-6-phenyltetrahydropyran-2-iminium perchlorates, which by treatment with aqueous ethanol were converted into the corresponding derivatives of pyran-2-ones. More... »

PAGES

1146

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428011080057

DOI

http://dx.doi.org/10.1134/s1070428011080057

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1007170924


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