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On the Tautomerism of 2‐Phenacyl‐4‐pyrimidinones and Related Compounds
Author(s) -
Elguero José,
Goya Pilar,
Martinez Ana,
Rozas Isabel
Publication year - 1989
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19891220521
Subject(s) - tautomer , chemistry , phenacyl , pyrimidinones , computational chemistry , keto–enol tautomerism , ketone , medicinal chemistry , organic chemistry
3‐Methyl‐2‐phenacyl‐4‐pyrimidinones 1 , 2 have been synthesized using the sulfide contraction. According to the NMR data, the compounds 1 , 2 exist exclusively as the benzoylmethylene tautomers a both in solution and in the solid state. AM1 calculations of the parent system are in agreement with the experimental observations. The study of the tautomeric equilibrium by this semiempirical method has been extended to other cases of enamino‐ketone/enolimine tautomerism.