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Synthesis of novel 3,4‐dihydropyrimidinones on water soluble solid support catalyzed by indium triflate
Author(s) -
Shanmugam P.,
Annie G.,
Perumal P. T.
Publication year - 2003
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.5570400521
Subject(s) - chemistry , trifluoromethanesulfonate , catalysis , combinatorial chemistry , steric effects , microwave irradiation , organic chemistry
Syntheses of several new 3,4‐dihydropyrimidinones (DHPMs) on sodium sulfate solid support have been reported. The microwave enhanced rapid synthesis of the title compounds yielded a good percentage of the DHPMs. The catalytic activity of indium triflate enables to prepare a wide range of DHPMs. Syntheses of 2‐hydroxyphenyl, 2‐hydroxy‐4‐methoxyphenyl pendant groups on DHPMs scaffold are advantages of the present method, which are rather prone towards cyclization and the presence of free hydroxyl groups on the phenyl ring is confirmed via D 2 O exchange study. The mechanism of the reaction is expected to proceed via absorption of substrates on the solid support followed by promotion of the reaction by In(OTf) 3 coupled with microwave irradiation.