Route to Highly Substituted Pyridines

Pyridine rings are common structural motifs found in a number of biologically active compounds, including some top-selling pharmaceuticals. We have developed a new approach to access substituted pyridines. The method aims to provide a reliable synthesis of a diverse range of substituted pyridines th...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 81; no. 21; pp. 10376 - 10382
Main Authors Hilf, Justin A, Holzwarth, Michael S, Rychnovsky, Scott D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
OLEFINATION
LIGANDS
SYNTHESE SUBSTITUIERTER PYRIDINE
CHEMISTRY
ELECTRON-DEFICIENT ARENES
CONDENSATION
DERIVATIVES
ALLYLTRIMETHYLSILANE
CONJUGATE ADDITION
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Summary:Pyridine rings are common structural motifs found in a number of biologically active compounds, including some top-selling pharmaceuticals. We have developed a new approach to access substituted pyridines. The method aims to provide a reliable synthesis of a diverse range of substituted pyridines through a three-step procedure. Readily available enones are first converted into 1,5-dicarbonyls through a two-step Hosomi–Sakurai allylation/oxidative cleavage sequence, which is followed by subsequent cyclization to the corresponding pyridine using hydroxylamine hydrochloride. A variety of substituted pyridines have been synthesized using this method.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01370