An effective method has been developed for the synthesis of N-(4-oxo(thioxo)-1,3,5-triazinan-1-yl)-arylamides by heterocyclization of (thio)carbamides with hydrazides of aromatic carboxylic acids and bis(N,N-dimethylamino)methane, using samarium salts as catalysts.
Similar content being viewed by others
References
H. Petersen, Synthesis, 243 (1973).
D. B. Lazarev, S. M. Ramsh, and A. G. Ivanenko, Zh. Obshch. Khim., 70, 475 (2000). [Russ. J. Gen. Chem., 70, 442 (2000).]
E. N. Garibov, I. A. Rzaeva, N. G. Shihaliev, A. I. Kuliev, V. M. Farzaliev, and M. A. Allahverdiev, Zh. Prikl. Khim., 83, 655 (2010). [Russ. J. Appl. Chem., 83, 707 (2010).]
A. Dandia, A. Kapil, and M. Sati, Synth. Commun., 34, 1141 (2004).
P. T. Kaye and X. W. Nocanda, ARKIVOC, vi, 923 (2000).
O. N. Gorbatova, A. V. Zherbev, and O. V. Koroleva, Usp. Biol. Khim., 46, 323 (2006).
M. D. Mashkovskii, Drugs, Novaya Volna, Moscow (2008), p. 991.
M. Movassaghi, D. S. Siegel, and S. Han, Chem. Sci., 1, 561 (2010).
M. D'Ambrosio, A. Guerriero, C. Debitus, O. Ribes, J. Pusset, S. Leroy, and F. Pietra, J. Chem. Soc., Chem. Commun., 1305 (1993).
M. Walter and L. Heilmeyer, Antibiotika–Fibel, Thieme Verlag, Stuttgart (1965), S. 419.
R. R. Hairullina, A. R. Geniyatova, A. G. Ibragimov, and U. M. Dzhemilev, Zh. Org. Khim., 49, 918 (2013). [Russ. J. Org. Chem., 49, 904 (2013).]
R. R. Hairullina, B. F. Akmanov, R. V. Kunakova, A. G. Ibragimov, and U. M. Dzhemilev, Izv. Akad. Nauk, Ser. Khim., 98 (2013). [Russ. Chem. Bull., Int. Ed., 62, 98 (2013).]
M. Tramontini and L. Angiolini, Tetrahedron, 46, 1791 (1990).
Yu. N. Kukushkin, The Reactivity of Coordination Compounds [in Russian], Khimiya, Leningrad (1987), p. 115.
The work received financial support from the Russian Foundation for Basic Research (projects 13-03-12027 ofi_m, 14-03-00240 _a, 14-03-97023 r_povolzhye_a, and 14-03-31360 mol_a), and from the Federal Agency of Science and Innovations (grant by the President of the Russian Federation NSh-2136.2014.3).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 777-781, May, 2014.
Rights and permissions
About this article
Cite this article
Hairullina, R.R., Geniyatova, A.R., Ibragimov, A.G. et al. Synthesis of N-(4-oxo(thioxo)-1,3,5-triazinan-1-yl)arylamides Using Samarium-Containing Catalysts. Chem Heterocycl Comp 50, 715–719 (2014). https://doi.org/10.1007/s10593-014-1525-0
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-014-1525-0