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4‐Hydroxy‐6‐methyl‐2‐pyrone (triacetic acid lactone) and its 3‐phenylthiomethyl derivative towards aldehydes in the presence of piperidine
Author(s) -
MorenoMañas M.,
Papell E.,
Ribas J.,
Virgili A.,
Pleixats R.
Publication year - 1986
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.5570230220
Subject(s) - chemistry , piperidine , thiophenol , lactone , pyrone , derivative (finance) , organic chemistry , reactivity (psychology) , stereochemistry , medicine , alternative medicine , pathology , financial economics , economics
Aldehydes react with triacetic acid lactone, 1 , in the presence of piperidine to afford the pyrones 3a‐d and 5 . The intermediacy of quinone‐methides of type 2a‐e has been postulated, and experimental evidence for their existence has been achieved by generation by thiophenol elimination from 7 and subsequent trapping in Diels‐Alder reactions. Two examples are given in reactivity of 7 at the sluggish C‐5 position.