ISSN 0235-7216
ISSN 2424-4538 (online)
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2015 m. Nr. 2
2,4-Diazidopyrrolo[2,3-d]pyrimidines: synthesis, ring–chain tautomerism and Cu(I)-catalyzed azide–alkyne cycloaddition reaction
Jonas BUCEVIČIUS, Sigitas TUMKEVIČIUS
2,4-Diazidopyrrolo[2,3-d]pyrimidines were synthesized by the reaction of the corresponding 2,4-dichloropyrrolo[2,3-d]pyrimidines with sodium azide at room temperature. 2,4-Diazidopyrrolo[2,3-d]pyrimidines were shown to exist in an equilibrium with the corresponding 5-azidopyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine. The proportion of the tetrazole tautomer increases with increasing solvent polarity. The CuAAC reaction of the obtained azides with 3-methylphenyl- and 4-biphenylylethynes afforded the corresponding 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines
Keywords: azides, nitrogen heterocycles, tautomerism, 1,2,3-triazoles, cycloaddition reaction
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