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Functionalization of substituted 2‐(1 H )pyridones. I. A novel synthesis of a‐arylgyloxylates and related systems
Author(s) -
Showalter H. D. Hollis,
Haskell Theodore H.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180228
Subject(s) - synthon , chemistry , surface modification , acetonitrile , trimethylsilyl , combinatorial chemistry , polarity (international relations) , organic chemistry , biochemistry , cell
A novel synthetic strategy is presented in which the heteroaryl[(trimethylsilyl)oxy]acetonitrile intermediate 3 is utilized either as a homologation or reverse‐polarity synthon for convenient entry into its corresponding α‐hydroxy‐ and α‐ketoarylalkanoate 4 and 6 , respectively. Further functionalization, including a stereo‐selective oximation procedure, is described.