Tetrahydropyridinediols and related aldehydes from the reactions of pyridine N‐oxide with mercaptans
- 1 April 1976
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 13 (2) , 321-328
- https://doi.org/10.1002/jhet.5570130224
Abstract
A new series of tetrahydropyridines was isolated when 1‐adamantyl or t‐butyl mercaptan was added last to a solution of pyridine N‐oxide and triethylamine in acetic anhydride. Under these conditions, the predominant tetrahydropyridines proved to be 1‐acetyl‐2‐alkylthio‐3‐acetoxy‐6‐hydroxy‐1,2,3,6‐tetrahydropyridines. These carbinolamides were isomerized in part during silica gel column chromatography to trans‐4‐acetoxy‐5‐alkylthio‐5‐acetamido‐2‐pentenals.Keywords
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