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Title: Synthesis of fused dihydropyrimidinones from cyclic-1,3-dicarbonyl compounds: Modified Biginelli synthesis of 1,2,3,4,5,6,7,8-octahydroquinazolinediones and 3 ,4-dihydro-l H -indeno [1,2-d] pyrimidine-2,5-diones
Authors: Shanmugam, Pachaiyappan
Sabastein, Cruz
Perumal, Paramasivan T
Issue Date: Jan-2004
Publisher: NISCAIR-CSIR, India
Abstract: Syntheses of bicyclo-3,4-dihydropyrimidinediones from cyclic 1,3-diketones such as 5,5-dimethyl-1, 3- cyclohexanedione (dimedone) and 1,3- indanedione have been attempted. During the multicomponent coupling of dimedone with (thio)urea and aldehydes, the unprecedented products of 9-aryl xanthene derivatives are obtained instead of the expected 4-aryl-1,2,3,4,5,6,7,8-octahydroquinazolinediones. Also, this reaction is senstive to solvent and the mole ratio of the ingredients used. High yields of bicyclic and tricyclic DHPMs with good selectivity are obtained using excess of urea and 1,3-dicarbonyl compounds. Interestingly, DHPMs are also formed in good to excellent yields by neat stirring of 1,3-dicarbonyl compounds, aldehydes and urea, keeping oil -bath temperature at 110°C. The mechanistic aspects of the reaction are also mentioned.
Page(s): 135-140
ISSN: 0975-0975(Online); 0376-4710(Print)
Appears in Collections:IJC-B Vol.43B(01) [January 2004]

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