F. A. Khaliullin, E. E. Klen
2010
Citations
0
Influential Citations
0
Citations
Journal
ChemInform
Abstract
Several methods of synthesis of 6,7-dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones have been reported, e.g., from 8-brom-7-(2-haloethyl)-3,7-dihydro1H-purine-2,6-diones and sodium sulfide [1], by reaction of 8-halo-7-(thiiran-2-ylmethyl)-3,7-dihydro-1Hpurin-2,6-diones with nucleophilic reagents [2], etc. We now propose a new one-step procedure for the preparation of 6,7-dihydro[1,3]thiazolo[2,3-f]purin2,4(1H,3H)-dione derivatives via reaction of 8-halo3,7-dihydro-1H-purine-2,6-diones with thiiranes. The reactions were carried out in DMF with 8-halo-3,7-dihydro-1H-purine-2,6-diones Ia–Ic as free bases (in the presence of a base) or potassium salts and an equimolar amount of thiirane IIa–IIc. 6,7-Dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones IIIa–IIIc were thus obtained in 59–68% yield.