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Paper | Special issue | Vol 74, No. 1, 2007, pp.369-382
Published online, 4th October, 2007
DOI: 10.3987/COM-07-S(W)15
Synthesis of New 1,3,8-Trisubstituted Purine-2,6-diones and 1,3,6-Trisubstituted Thiazolo[2,3-f]purine -2,4-diones

Alaa M. Hayallah and Michael Famulok*

*Institute of Chemical Biology and Medicinal Chemistry Unit, University of Bonn, Gerhard-Domagk-Str.1, D-53121 Bonn, Germany


New 1,3,8-trisubstituted purine-2,6-diones and 1,3,6-trisubstituted thiazolo[2,3-f]purine-2,4-diones were designed and synthesized as agents with potential biological activities. The final products were obtained by cyclization of carboxamide intermediates using 1,1,1,3,3,3,-hexamethyldisilazane. This procedure gave higher yields, and was more convenient and easier in purification compared to other methods. We also found polyphosphoric acid to be the most efficient agent in the cyclization of 8-[2-(p-(un)substituted-phenyl)-2-oxo-ethylsulfanyl]-1,3-dipropyl-3,7-dihydro-purine-2,6-diones to 1,3-dipropyl-6-substituted)-1H-thiazolo[2,3-f]purine-2,4-diones.