Abstract
C-Phosphorylation of 2-thiazolylformamidines by phosphorus tribromide was studied. It was shown that the 1,3-diazabut-1-enyl (formamidine) substituent can be used as both an activating and protective group. 5-Phosphorylated thiazoles containing either a formamidine fragment or an amino group were obtained. Some properties of the compounds synthesized were studied.
Similar content being viewed by others
References
M. I. Kabachnik and T. Ya. Medved',Dokl. Akad. Nauk SSSR, 1952,83, 689.
E. K. Fields,J. Am. Chem. Soc., 1952,74, 1528.
V. P. Kukhar' and V. A. Solodenko,Usp. Khim., 1986,59, 1504 [Russ. Chem. Rev., 1986,59 (Engl. Transl.)].
M. I. Kabachnik, T. Ya. Medved', N. M. Dyatlova, and M. V. Rudomino,Usp. Khim., 1974,43, 1554 [Russ. Chem. Rev., 1974,43 (Engl. Transl.)].
A. A. Tolmachev, G. V. Oshovskii, A. S. Merkulov, and A. M. Pinchuk,Khim. Geterotsikl. Soedin. 1996, 1288 [Chem. Heterocycl. Compd., 1996 (Engl. Transl.)].
G. V. Oshovskii, A. A. Tolmachev, A. S. Merkulov, and A. M. Pinchuk,Khim. Geterotsikl. Soedin., 1997, 1422 [Chem. Heterocycl. Compd., 1997 (Engl. Transl.)].
E. D. Raczynska and T. Drapala,J. Chem. Res. (S), 1993, 54.
D. K. Anderson, D. L. Deuwer, and J. A. Sikorski,J. Heterocycl. Chem., 1995,32, 893.
D. Redmore,Chem. Rev., 1971,71, 315.
V. S. Brovarets, K. V. Zyuz' R. N. Vydzhak, T. K. Vinogradova, and B. S. Drach,Zh. Obshch. Khim., 1994,64, 1642 [Russ. J. Gen. Chem. 1994,64, (Engl. Transl.)].
The Chemistry of Amidines and Imidates, Ed. S. Patai, J. Wiley and Sons, 1975, 603.
E. D. Raczynska, C. Laurence, and P. Nicolet,J. Chem. Soc., Perkin Trans. 2, 1988, 1491.
A. A. Tolmachev, A. S. Merkulov, G. V. Oshovskii, and A. B. Rozhenko,Zh. Obshch. Khim., 1996,66, 1930 [Russ. J. Gen. Chem., 1996,66 (Engl. Transl.)].
A. A. Tolmachev, A. S. Merkulov, and G. V. Oshovskii,Khim. Geterotsikl. Soedin., 1997, 1000 [Chem. Heterocycl. Compd., 1997 (Engl. Transl.)].
A. A. Tolmachev, A. A. Yurchenko, M. G. Semenova, and N. G. Feshchenko,Zh. Obshch. Khim., 1993,63, 714 [Russ. J. Gen. Chem., 199363 (Engl. Transl.)].
P. N. Gaponik, Yu. V. Grigor'ev, and V. P. Karavai,Khim. Geterotsikl. Soedin.; 1985, 566 [Chem. Heterocycl. Compd., 1985 (Engl. Transl.)].
M. L. Weiner,J. Org. Chem., 1960,25, 2245.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1353–1359, July, 1999.
Rights and permissions
About this article
Cite this article
Oshovskii, G.V., Tolmachev, A.A., Yurchenko, A.A. et al. C-PhosphorylatedN 2-2-thiazolylformamidines. Russ Chem Bull 48, 1341–1347 (1999). https://doi.org/10.1007/BF02495301
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02495301