Caesium carbonate promoted regioselective O-functionalization of 4,6-diphenylpyrimidin-2(1H)-ones under mild conditions and mechanistic insight
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Date
2023-06-05T00:00:00
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Publisher
Royal Society of Chemistry
Abstract
A facile one-step catalyst free methodology has been developed for the regioselective functionalization of 4,6-diphenylpyrimidin-2(1H)-ones under mild conditions. Selectivity towards the O-regioisomer was achieved by using Cs2CO3 in DMF without use of any coupling reagents. A total of 14 regioselective O-alkylated 4,6-diphenylpyrimidines were synthesized in 81-91% yield. In the DFT studies it was observed that the transition state for the formation of the O-regioisomer is more favourable with Cs2CO3 as compared to K2CO3. Furthermore, this methodology was extended to increase the O/N ratio for the alkylation of 2-phenylquinazolin-4(3H)-one derivatives. � 2023 The Royal Society of Chemistry.
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Keywords
Potash, Regioselectivity, Catalyst-free, Condition, Coupling reagents, DFT study, Functionalizations, Mechanistics, Regio-selective, Regioisomers, Regioselective functionalization, Synthesised, Cesium compounds