Abstract
The α-ureidoalkylation of imidazolidine-2,4-dione, urea, carboxylic acid amides, and sulfonamides has been studied using 1,3-bis(hydroxymethyl)-imidazolidin-2-one as ureidoalkylating agent. Methods have been developed for the synthesis of 1,3-bis(2,4-dioxoimidazolidin-1-ylmethyl)-, 1,3-bis(acetylaminomethyl)-, 1,3-bis(benzoylaminomethyl)-, 1,3-bis(phenylsulfonylaminomethyl)-, and 1,3-bis(p-toluenesulfonylaminomethyl)imidazolidin-2-ones.
Similar content being viewed by others
References
E. Jagiello-Wojtowicz, I. Zebrowska-Lupina, M. Wielosz, M. Stelmasiak, G. Szurska, A. Porowska, and Z. Kleinrok, Acta Polon. Pharm., 41, 495 (1984).
W. J. Brouillette, V. P. Jestkov, M. L. Brown, and M. S. Akhar, J. Med. Chem., 37, 3289 (1994).
M. D. Mashkovskii, Drugs [in Russian], Vol. 1, Novaya Volna, Moscow (2000), p. 146.
N. N. Melnikov, K. V. Novozhilov, and S. R. Belan, Handbook. Pesticides and Growth Regulators [in Russian], Khimiya, Moscow (1995), p. 81.
A. N. Kravchenko, A. S. Sigachev, E. Yu. Maksareva, G. A. Gazieva, N. S. Trunova, B. V. Lozhkin, T. S. Pivina, M. M. Ilin, Yu. V. Nelyubina, V. A. Davankov, O. V. Lebedev, N. N. Makhova, and V. A. Tartakovskii, Izv. Akad. Nauk, Ser. Khim., 680 (2005).
A. N. Kravchenko, E. Yu. Maksareva, P. A. Belyakov, A. S. Sigachev, K. Yu. Chegaev, K. A. Lyssenko, O. V. Lebedev, and N. N. Makhova, Izv. Akad. Nauk, Ser. Khim., 180 (2003).
A. N. Kravchenko and I. E. Chikunov, Usp. Khim., 75, 217 (2006).
A. S. Sigachev, A. N. Kravchenko, K. A. Lysenko, P. A. Belyakov, O. V. Lebedev, and N. N. Makhova, Izv. Akad. Nauk, Ser. Khim., 836 (2006).
G. A. Gazieva, A. N. Kravchenko, O. V. Lebedev, and V. I. Abelentsev, Khim.-farm. Zh., 35, No. 2, 14 (2001).
G. A. Petropavlovskii, Zh. Prikl. Khim., 42, 2072 (1969).
B. V. Zametta, N. V. Platonova, and I. B. Klimenko, Zh. Prikl. Khim., 44, 1916 (1971).
Yu. Miyahara, K. Goto, M. Oka, and T. Inazu, Angew. Chem., 38, 5019 (2004).
H. Staudinger and G. Niessen, Makromol. Chem., 15, 75 (1995).
A. V. Bogatsky, N. G. Lukyanenko, V. N. Pastushok, and R. G. Kostyanovsky, Synthesis, 992 (1983).
A. S. Galabov, E. Velichkova, A. Karparov, D. Sidzhakova, D. Danchev, and N. Chakova, Arzneim.-Forsch., 34, 9 (1984).
A. S. Sigachev, A. N. Kravchenko, E. Yu. Maksareva, B. V. Lozhkin, K. A. Lyssenko, and N. N. Makhova, Mendeleev Commun., 80 (2006).
G. F. Whitfield, H. S. Beilan, D. Saika, and D. Swern, J. Org. Chem., 39, 2148 (1974).
A. B. Pepperman, D. J. Daigle, and S. L. Vail, J. Org. Chem., 41, 675 (1976).
R. Roesch and M. H. Gold, J. Am. Chem. Soc., 73, 2959 (1951).
D. J. Dusemund, Arch. Pharm. (Weinheim), 310, 404 (1977).
D. J. Dusemund and T. Schurreit, Arch. Pharm. (Weinheim), 319, 826 (1986).
Author information
Authors and Affiliations
Corresponding author
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1655–1659, November, 2007.
Rights and permissions
About this article
Cite this article
Gazieva, G.A., Lozhkin, P.V. & Kravchenko, A.N. α-Ureidoalkylation of 1,3-bis(hydroxymethyl)-imidazolidin-2-one. Chem Heterocycl Comp 43, 1406–1410 (2007). https://doi.org/10.1007/s10593-007-0217-4
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-007-0217-4