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Palladium‐catalyzed conjugate addition type reaction of 5‐iodopyrimidines with α,β‐unsaturated ketones
Author(s) -
Wada Akimori,
Ohki Kazuhiro,
Nagai Sotoo,
Kanatomo Shōichi
Publication year - 1991
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.5570280259
Subject(s) - chemistry , triethylamine , conjugate , triphenylphosphine , steric effects , palladium , medicinal chemistry , pyrimidine , catalysis , double bond , ring (chemistry) , addition reaction , organic chemistry , stereochemistry , mathematical analysis , mathematics
The reaction of various 5‐iodopyrimidines with α,β ‐unsaturated ketones in the presence of palladium diacetate‐triphenylphosphine complex in triethylamine are investigated. In the reaction of 2,4‐dialkoxy(or alkylthio)‐6‐methyl‐5‐iodopyrimidine the addition of pyrimidine to the carboncarbon double bond of α,β ‐unsaturated ketones occurs. In the case of other pyrimidines, according to the decrease of steric hindrance at the 5‐position on the pyrimidine ring, the ratio of conjugate addition product was decreased and the usual olefinic substituted product was increased.