Premium
Pyridinethiones. XI. Diastereoselective aldol condensations with 2(1 H )‐pyridones, 2(1 H )‐pyridinethiones, and the crystal structure of 3‐(1‐hydroxy‐2‐methyl‐3‐oxo‐3‐(4‐chlorophenyl)propyl‐1‐isoprpyl‐2(1 H )‐pyridinethione
Author(s) -
Becher Jan,
Asaad Fahmy M.,
Johansen Tea,
Hansen Jesper,
Larsen Sine,
Hansen Flemming
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.5570230252
Subject(s) - chemistry , propiophenone , aldol reaction , aldol condensation , benzaldehyde , methyl vinyl ketone , diastereomer , condensation , medicinal chemistry , stereochemistry , ketone , organic chemistry , catalysis , physics , thermodynamics
Aldol condensation of 3‐formyl‐2(1 H )‐pyridinethiones and the corresponding pyridones with ketones such as acetophenones in aqueous base yields 3‐hydroxy‐1‐propanones in high yields. Reaction with propiophenone showed this reaction to be highly diastereoselective as only the erythro ‐isomer is formed at room temperature. This assignment was based on an X‐ray crystallographic investigation of the compound given in the title. Aldol condensations of a number of related 3‐acetyl‐2(1 H )‐pyridinethiones with benzaldehyde yielded the corresponding trans ‐vinyl ketones.