Abstract
A new method was developed for the synthesis of 1-(2-tetrahydrofuryl) derivatives of uracil, 5-substituted uracils, 6-azauracil, and cytosine by alkylation of 2,4-bis(trimethylsilyl) derivatives of pyrimidine bases with 2-acetoxytetrahydrofuran in the presence of Lewis acids. In contrast to 2-chlorotetrahydrofuran, which is used in a previously described method, 2-acetoxytetrahydrofuran is stable at room temperature and reacts under these conditions with silyl derivatives of uracils in the presence of SnCl4 to give 1-(2-tetrahydrofuryl) derivatives of pyrimidine bases in 80–85% yields.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
S. A. Hiller (Giller), D. E. Zarin, and R. A. Zhuk, Nucleic Acids Res., 3, 721 (1976).
D. Ya. Sniker, R. A. Zhuk, É. I. Stankevich, G. Ya. Dubur, and S. A. Giller, Khim. Geterotsikl. Soedin., No. 2, 170 (1969).
S. A. Giller, M. Yu. Lidak, R. A. Zhuk, É. A. Berzinya, K. Ya. Pets, I. N. Getsova, and É. L Bruk, Khim. Geterotsikl. Soedin., No. 3, 375 (1969).
S. A. Giller, R. A. Zhuk, A. É. Berzin', L. A. Sherin', and A. A. Lazdyn'sh, U.S. Patent No. 3912734 (1975).
U. Nidballa and H. Vorbrüggen, J. Org. Chem., 39, 3654 (1974).
H. Normant, Compt. Rend., 226, 185 (1948).
S. A. Giller, R. A. Zhuk, and M. Yu. Lidak, Dokl. Akad. Nauk SSSR, 176, 332 (1967).
C. W. Noell and C. C. Cheng, J. Heterocycl. Chem., 5, 25 (1968).
Author information
Authors and Affiliations
Additional information
See [1] for communication X.
Deceased.
Translated from Khimiya Geterotsiklicheskikh Soedineaii, No. 9, pp. 1258–1259. September, 1977.
Rights and permissions
About this article
Cite this article
Zhuk, R.A., Berzinya, A.É., Sherin', L.A. et al. Analogs of pyrimidine nucleosides. Chem Heterocycl Compd 13, 1015–1016 (1977). https://doi.org/10.1007/BF00472462
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00472462