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A novel non photochemical ring contraction of 4‐pyrones to cyclopent‐2‐enones
Author(s) -
Jakopčic K.,
Kojić J.,
Orhanović Z.,
Stiplošek Z.,
Nagl A.,
Hergold A.
Publication year - 1992
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.5570290118
Subject(s) - chemistry , cyclopentenone , contraction (grammar) , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , medicine
Unlike comenic acid or most other 4‐pyrones, methyl or ethyl comenate reacts with aromatic amines under mild conditions in the sense of ring contraction to 3‐arylamino‐2,4‐dihydroxy‐2‐cyclopentenone‐4‐carboxylates. The structure of the new cyclopentenone derivatives were determined from their characteristic spectroscopic behaviour and was confirmed by X‐ray crystallographic studies of compound Vb .