A rapid and facile synthesis of new spiropyrimidines from 5-(2-arylethylidene-2-oxo)-1,3-dimethylpyrimidine-2,4,6-triones / Gozalishvili L.L., Beryozkina T.V., Omelchenko I.V., Zubatyuk R.I., Shishkin O.V., Kolos N.N. // Tetrahedron. - 2008. - V. 64, l. 37. - P. 8759-8765.

ISSN:
00404020
Type:
Article
Abstract:
A series of new tetraazaspiro[5,5]-undec-4-ene-2,7,9,11-tetraones have been obtained by reaction of 5-(2-arylethylidene-2-oxo)-1,3-dimethylpyrimidine-2,4,6-triones with ureas. A three-component one-pot procedure to the spiranes synthesis was also developed. One-pot reaction of arylglyoxals, 1,3-dimethylbarbituric acid, and dimethylurea led to imidazolyl-1,3-dimethylbarbituric acids. Mechanisms of studied reactions were discussed. © 2008 Elsevier Ltd. All rights reserved.
Author keywords:
α,β-Unsaturated ketones; Arylglyoxals; Knoevenagel reaction; One-pot synthesis; Spiropyrimidines; Ureas
Index keywords:
barbituric acid derivative; dimethylurea; glyoxal derivative; pyrimidine derivative; urea; article; carbon nuclear magnetic resonance; chemical reaction; one pot synthesis; priority journal; proton nu
DOI:
10.1016/j.tet.2008.06.097
Смотреть в Scopus:
https://www.scopus.com/inward/record.uri?eid=2-s2.0-48049114187&doi=10.1016%2fj.tet.2008.06.097&partnerID=40&md5=6bc1d60c3ef4d98dc423c74e35d9e2e7
Соавторы в МНС:
Другие поля
Поле Значение
Link https://www.scopus.com/inward/record.uri?eid=2-s2.0-48049114187&doi=10.1016%2fj.tet.2008.06.097&partnerID=40&md5=6bc1d60c3ef4d98dc423c74e35d9e2e7
Affiliations Organic Chemistry Department, V.N. Karazin Kharkiv National University, Svoboda sq. 4, 61077 Kharkiv, Ukraine; STC 'Institute of Single Crystals', Lenina ave. 60, 61001 Kharkiv, Ukraine
Author Keywords α,β-Unsaturated ketones; Arylglyoxals; Knoevenagel reaction; One-pot synthesis; Spiropyrimidines; Ureas
Chemicals/CAS dimethylurea, 1320-50-9; urea, 57-13-6
References Tietze, L.F., (1996) Chem. Rev., 96, p. 115; Parsons, P.J., Penkett, C.S., Shell, A.I., (1996) Chem. Rev., 96, p. 195; Ishmuratov, G.Yu., Kharisov, R.Ya., Latypova, E.R., Talipov, R.F., (2006) Chem. Nat. Compd., 42, p. 367; Dhar, N.D., (1981) The Chemistry of Chalcones and Related Compounds, , Wiley-Interscience, New York, NY 285; March, J., Smith, M.B., (2007) Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, , Wiley-Interscience, New York, NY 2357; Kolos, N.N., Orlov, V.D., Chebanov, V.A., Shishkin, O.V., Kulikov, A.Yu., (1999) Chem. Heterocycl. Compd., 9, p. 1230; Kolos, N.N., Orlov, V.D., Arisa, D., (1996) Chem. Heterocycl. Compd., 1, p. 87; Kolos, N., Beryozkina, T., Orlov, V., (2003) Heterocycles, 60, p. 2115; Kolos, N.N., Beryozkina, T.V., Orlov, V.D., (2002) Mendeleev Commun., p. 91; Desenko, S.M., (1994) Chem. Heterocycl. Compd., 30, p. 125; Toth, G., Levai, A., Szollosy, A., (1992) Liebigs Ann. Chem., p. 803; Krause, N., Hoffmann-Roder, A., (2001) Synthesis, 2, p. 171; Hakiki, A., Mossadak, M., Mokhles, M., Duddeck, H., Nikhlova, B., (1995) Tetrahedron, 51, p. 2293; Negwer, M., (1994) Organic-Chemical Drugs and their Synonyms. 7th revised and enlarged ed., 4. , Akademie, Berlin pp 2873, 2957; Kolos, N.N., Orlov, V.D., Chebanov, V.A., Shishkin, O.V., Kuznetsov, V.P., Kulikov, A.Yu., (1996) Chem. Heterocycl. Compd., p. 978; Kolos, N.N., Beryozkina, T.V., Yaremenko, F.G., Enina, L.S., Musatov, V.I., (2005) Funct. Mater., 12, p. 569; Ramasamy, K., Imamura, N., Hanna, N.B., Finch, R.A., Avery, T.L., Robins, R.K., Revankar, G.K., (1990) J. Med. Chem., 33, p. 1220; Bhattachary, B.K., Ojwang, J.O., Rando, R.F., Huffman, J.H., Rewankar, G.R., (1995) J. Med. Chem., 38, p. 3957; Figueras, J., (1966) J. Org. Chem., 31, p. 803; Sabri, S.S., Hussein, A.Q., Al-Hajjar, F.H., (1985) J. Chem. Eng. Data, 30, p. 512; Burgi, H.-B., Dunitz, J.D., (1994) Structure Correlation, 2. , VCH, Weinheim 741; Zefirov, Yu.V., Zorkii, P.M., (1989) Russ. Chem. Rev., 58, p. 421; Balalai, S., Soleiman, M., Rominger, F., (2005) J. Iran. Chem. Soc., 2, p. 319; Al-Hajjar, F.H., Al-Farkh, Y.A., Hamoud, H.S., (1979) Can. J. Chem., 57, p. 2734; Mamaev, V.P., Weis, A.L., (1975) Khim. Geterotsikl. Soedin., p. 1555; Weis, A.L., Mamaev, V.P., (1977) Khim. Geterotsikl. Soedin., p. 674; Butler, A.R., Hussain, J., Leitch, E., (1980) J. Chem. Soc., Perkin Trans. 2, p. 106; Sheldrick, G.M., (1998) SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data, , Bruker AXS, Madison, Wisconsin, USA Rev. 5.1; Spek, A.L., (2001) PLATON, , University of Utrecht, The Netherlands
Correspondence Address Kolos, N.N.; Organic Chemistry Department, V.N. Karazin Kharkiv National University, Svoboda sq. 4, 61077 Kharkiv, Ukraine; email: kolos@univer.kharkov.ua
CODEN TETRA
Language of Original Document English
Abbreviated Source Title Tetrahedron
Source Scopus