2008
DOI: 10.1016/j.tet.2008.06.097
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A rapid and facile synthesis of new spiropyrimidines from 5-(2-arylethylidene-2-oxo)-1,3-dimethylpyrimidine-2,4,6-triones

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Cited by 28 publications
(7 citation statements)
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“…Again, Nmethylated pyrrolo [2,3-d]pyrimidine-2,4-diones were more reactive than the partially unsubstituted pyrrolo [2,3-d] pyrimidine-2,4-diones. However, although the condensation of glyoxal [B] and 1,3-dimethylbarbituric acid 4 took place very easily, 24 the Michael addition of pyrrolo [2,3-d]pyrimidine-2,4diones 1 to the condensed product did not occur under our reaction conditions (Scheme 4). It might be because of the keto group which deactivates the nucleophilic addition.…”
Section: Resultsmentioning
confidence: 90%
“…Again, Nmethylated pyrrolo [2,3-d]pyrimidine-2,4-diones were more reactive than the partially unsubstituted pyrrolo [2,3-d] pyrimidine-2,4-diones. However, although the condensation of glyoxal [B] and 1,3-dimethylbarbituric acid 4 took place very easily, 24 the Michael addition of pyrrolo [2,3-d]pyrimidine-2,4diones 1 to the condensed product did not occur under our reaction conditions (Scheme 4). It might be because of the keto group which deactivates the nucleophilic addition.…”
Section: Resultsmentioning
confidence: 90%
“…Gozalishvili et al described a similar reaction using 1,3-dimethylbarbituric acid 136 . The reaction was conducted by heating the solution of equimolar amounts of 136 , AGs, and 116 in MeOH in the presence of a catalytic amount of AcOH under reflux conditions for 25–40 min to produce imidazol-4-yl-pyrimidine-2,4,6-triones 137 in 62–87% yields (Scheme ).…”
Section: Synthesis Of Five-membered Heterocyclesmentioning
confidence: 99%
“…(D) The interaction of 1,3-dimethylbarbituric acid, glyoxals, and DMU in methanol with a catalytic amount of glacial acetic acid led to 5-(5-aryl-1,3-dimethyl-2-oxo-2,3-dihydro-1H-imidazol-4-yl)-1,3-dimethylpyrimidine-2,4,6-triones. 7 (E) N-methyl imines can be synthesized by the reaction of DMU and aldehydes in the presence of solid clay-montmorrilonite K10. 8 (F) The regioisomeric diene DMU 1,2-adducts A/B were synthesized by reacting isoprene with DMU using palladium(II) catalyst (O 2 /cat.)…”
Section: Preparationmentioning
confidence: 99%