Biopolym. Cell. 1996; 12(6):82-86.
http://dx.doi.org/10.7124/bc.000459
The tetrahydrofuranylic derivatives of C6 substituted 3,5-dioxo- and 3,5-thioxo-1,2,4-triazines as a structural analogs of azapyrimidine nucleosides
1Palchikovskaya L. I., 1Alexeeva I. V., 1Shalamay A. S.
  1. Institute of Molecular Biology and Genetics, NAS of Ukraine
    150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680

Abstract

Influence of C6-aminoalkyl-, C6-mercaptoalkyl-substitutes of 3,5-dioxo- and 3,5-thioxo-derivatives 1,2,4-triazines on the process of tetrahydrofuranylation has been studied. This study was conducted in the conditions, similar to the one-step reaction of nucleic bases glycosylation. We discovered significant dependence of the regiospecifity of this reaction from electronic nature of substitutes in the 6-position.
Full text: (PDF, in Russian)

References

[1] Vorbr?ggen H. Methods of Nucleoside Synthesis. Nucleoside Analogues. Chemistry, Biolody and Medical Application. Ed. R. T. Walker. New York: Plenum press, 1980. Vol. 26: 35-69.
[2] Vorbruggen H, Benua B. Nucleoside Synthesis. XXIII. The One-Step. One-Pot-Reaction. Chem Ber. 1981. 114: 1280-5.
[3] Alekseeva IV, Pal’chikovskaya LI, Shalamai AS, Ognyanik SS, Morgart NV, Petrusha NA. Synthesis of N1-substituted 6-azacytosines and their biological activity. Pharmaceutical Chemistry Journal. 1994;28(4):227–30.
[4] Ognyanik SS, Tarnavsky SS, Kobylinskaya VI, Alekseeva IV, Shalamai AS. Glycosylation of 5-N-aminoacidic derivatives of 6-azauracyl and 2-thio-6-azauracyl. Ukr Khim Zh. 1988;54(10):1094-8.
[5] Wierenga W, Skulnick HI. Investigations of the mechanism of nucleoside synthesis. I. 13C-NMR studies of dihydro--triazine-SnCl4 complexes. Tetrahedron Lett. 1979;20(38):3631–4.
[6] Cristescu C. as-Triasin-Derivate, die moglieherweise therapeutische Wirkung besitzen, 15. Mitt.: Synthese von neuen blockierten 5-substituten 4-thio-6-azauridinen. Monatsh Chem. 1977; 108(6):1455-9.