Unusual sulfanylation through ring transformation of arene-tethered 2 H-pyran-2-ones by in situ built Michael adduct

A novel synthesis of highly functionalized alkylsulfanylmethyl arenes 8a– m through the ring transformation of 6-aryl-4-methyl/ethylsulfanyl-2 H-pyran-2-one-3-carbonitriles 1a– j, by reaction with methyl vinyl ketone 2, is delineated and illustrated. To ascertain the course of reaction, 3-arylsulfan...

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 22; pp. 3759 - 3762
Main Authors Sil, Diptesh, Pratap, Ramendra, Kumar, Rishi, Maulik, P.R., Ram, Vishnu Ji
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 2006
Subjects
2 H-Pyran-2-one
Ring transformation reactions
Sulfanylated arenes
Sulfanylated arenes
Ring transformation reactions
2 H-Pyran-2-one
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Summary:A novel synthesis of highly functionalized alkylsulfanylmethyl arenes 8a– m through the ring transformation of 6-aryl-4-methyl/ethylsulfanyl-2 H-pyran-2-one-3-carbonitriles 1a– j, by reaction with methyl vinyl ketone 2, is delineated and illustrated. To ascertain the course of reaction, 3-arylsulfanylmethyl-2-methyl-6-methylsulfanyl-4-phenylbenzonitriles 8k– m were also prepared from the reaction of 1 with 4-arylsulfanyl-butan-2-ones 7c, d.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.03.119