Three-component, one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by bromodimethylsulfonium bromide
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A. Shaabani
und
A. Maleki
Abstract
An efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives by one-pot three-component condensation reaction between an alkyl or aryl aldehyde, a 1,3-dicarbonyl compound, and urea or thiourea in the presence of catalytic amount of bromodimethylsulfonium bromide has been developed. The condensation product was obtained in excellent yields in refluxing ethanol and easily separated from the reaction mixture and purified.
[1] Kappe, C. O., Tetrahedron 49, 6937 (1993) and references cited therein. http://dx.doi.org/10.1016/S0040-4020(01)87971-010.1016/S0040-4020(01)87971-0Suche in Google Scholar
[2] Stefani, H. A., Oliveira, C. B., Almeida, R. B., Pereira, C. M. P., Braga, R. C., Cella, R., Borges, V. C., Savegnago, L., and Nogueira, C. W., Eur. J. Med. Chem. 41, 513 (2006). http://dx.doi.org/10.1016/j.ejmech.2006.01.00710.1016/j.ejmech.2006.01.007Suche in Google Scholar
[3] Reddy, C. V., Mahesh, M., Raju, P. V. K., Babu, T. R., and Reddy, V. V. N., Tetrahedron Lett. 43, 2657 (2002). http://dx.doi.org/10.1016/S0040-4039(02)00280-010.1016/S0040-4039(02)00280-0Suche in Google Scholar
[4] Fu, N. Y., Yuan, Y. F., Cao, Z., Wang, S. W., Wang, J. T., and Peppe, C., Tetrahedron 58, 4801 (2002). http://dx.doi.org/10.1016/S0040-4020(02)00455-610.1016/S0040-4020(02)00455-6Suche in Google Scholar
[5] Ranu, B. C., Hajra, A., and Jana, U., J. Org. Chem. 65, 6270 (2000). http://dx.doi.org/10.1021/jo000711f10.1021/jo000711fSuche in Google Scholar
[6] Ma, Y., Qian, C., Wang, L., and Yang, M., J. Org. Chem. 65, 3864 (2000). http://dx.doi.org/10.1021/jo991905210.1021/jo9919052Suche in Google Scholar
[7] Lu, J., Bai, Y., Wang, Z., Yang, B., and Ma, H., Tetrahedron Lett. 41, 9075 (2000). http://dx.doi.org/10.1016/S0040-4039(00)01645-210.1016/S0040-4039(00)01645-2Suche in Google Scholar
[8] Kumar, K. A., Kasthuraiah, M., Reddy, C. S., and Reddy, C. D., Tetrahedron Lett. 42, 7873 (2001). http://dx.doi.org/10.1016/S0040-4039(01)01603-310.1016/S0040-4039(01)01603-3Suche in Google Scholar
[9] Yadav, J. S., Reddy, B. V. S., Reddy, K. B., Raj, K. S., and Prasad, A. R., J. Chem. Soc., Perkin Trans. 1 2001, 1939. 10.1039/b102565cSuche in Google Scholar
[10] Bigi, F., Carloni, S., Frullanti, B., Maggi, R., and Sartori, G., Tetrahedron Lett. 40, 3465 (1999). http://dx.doi.org/10.1016/S0040-4039(99)00424-410.1016/S0040-4039(99)00424-4Suche in Google Scholar
[11] Kappe, C. O., Kumar, D., and Varma, R. S., Synthesis 1999, 1799. 10.1055/s-1999-3592Suche in Google Scholar
[12] Bussolari, J. C. and McDonnell, P. A., J. Org. Chem. 65, 6777 (2000). http://dx.doi.org/10.1021/jo005512a10.1021/jo005512aSuche in Google Scholar
[13] Yadav, J. S., Reddy, B. V. S., Reddy, E. J., and Ramalingam, T., J. Chem. Res., Synop. 2000, 354. 10.3184/030823400103167633Suche in Google Scholar
[14] Hu, E. H., Sidler, D. R., and Dolling, U. H., J. Org. Chem. 63, 3454 (1998). http://dx.doi.org/10.1021/jo970846u10.1021/jo970846uSuche in Google Scholar
[15] Shaabani, A., Bazgir, A., and Teimouri, F., Tetrahedron Lett. 44, 857 (2003). http://dx.doi.org/10.1016/S0040-4039(02)02612-610.1016/S0040-4039(02)02612-6Suche in Google Scholar
[16] Atwal, K. S., O’Reilly, B. C., Gougoutas, J. Z., and Malley, M. F., Heterocycles 26, 1189 (1987). http://dx.doi.org/10.3987/R-1987-05-118910.3987/R-1987-05-1189Suche in Google Scholar
[17] Atwal, K. S., Rovnyak, G. C., O’Reilly, B. C., and Schwartz, J., J. Org. Chem. 54, 5898 (1989). http://dx.doi.org/10.1021/jo00286a02010.1021/jo00286a020Suche in Google Scholar
[18] Saloutin, V. I., Burgart, Ya. V., Kuzueva, O. G., Kappe, C. O., and Chupakhin, O. N., J. Fluorine Chem. 103, 17 (2000). http://dx.doi.org/10.1016/S0022-1139(99)00216-X10.1016/S0022-1139(99)00216-XSuche in Google Scholar
[19] Furukawa, N., Inoue, T., Aida, T., and Oae, S., J. Chem. Soc., Chem. Commun. 1973, 212a. 10.1039/c3973000212aSuche in Google Scholar
[20] Olah, G. A., Yashwant, D. V., Massoud, A., and Suryaprakash, G. K., Synthesis 1979, 720. 10.1055/s-1979-28811Suche in Google Scholar
[21] Khan, A. T., Mondal, E., Ghosh, S., and Islam, S., Eur. J. Org. Chem. 2004, 2002 and references cited therein. 10.1002/ejoc.200300685Suche in Google Scholar
[22] Khan, A. T., Islam, S., Majee, A., Chattopadhyay, T., and Ghosh, S., J. Mol. Catal. A:Chem. 239, 158 (2005). http://dx.doi.org/10.1016/j.molcata.2005.05.04210.1016/j.molcata.2005.05.042Suche in Google Scholar
[23] Kudrimoti, S. and Bommena, V. R., Tetrahedron Lett. 46, 1209 (2005). http://dx.doi.org/10.1016/j.tetlet.2004.12.07010.1016/j.tetlet.2004.12.070Suche in Google Scholar
[24] Das, B., Ramu, R., Ravikanth, B., and Reddy, V. S., J. Mol. Catal. A: Chem. 246, 76 (2006). http://dx.doi.org/10.1016/j.molcata.2005.10.01510.1016/j.molcata.2005.10.015Suche in Google Scholar
[25] Das, B., Ravikanth, B., Thirupathi, P., and Rao, B. V., Tetrahedron Lett. 47, 5041 (2006). http://dx.doi.org/10.1016/j.tetlet.2006.05.10110.1016/j.tetlet.2006.05.101Suche in Google Scholar
[26] Das, B., Krishnaiah, M., and Venkateswarlu, K., Tetrahedron. Lett. 47, 4457 (2006). http://dx.doi.org/10.1016/j.tetlet.2006.04.05910.1016/j.tetlet.2006.04.059Suche in Google Scholar
[27] Das, B., Ramu, R., Ravikanth, B., and Reddy, K. R., Synthesis 2006, 1419. 10.1055/s-2006-926421Suche in Google Scholar
[28] Shaabani, A. and Bazgir, A., Tetrahedron Lett. 45, 2575 (2004). http://dx.doi.org/10.1016/j.tetlet.2004.01.15410.1016/j.tetlet.2004.01.154Suche in Google Scholar
[29] Shaabani, A., Bazgir, A., and Arab-Ameri, S., Phosphorus Sulfur 179, 2169 (2004). http://dx.doi.org/10.1080/1042650049047481510.1080/10426500490474815Suche in Google Scholar
[30] Shaabani, A. and Rahmati, A., Catal. Lett. 100, 177 (2005). http://dx.doi.org/10.1007/s10562-004-3451-810.1007/s10562-004-3451-8Suche in Google Scholar
[31] Shaabani, A., Rahmati, A., and Naderi, S., Bioorg. Med. Chem. Lett. 15, 5553 (2005). http://dx.doi.org/10.1016/j.bmcl.2005.08.10110.1016/j.bmcl.2005.08.101Suche in Google Scholar PubMed
[32] Folkers, K., Harwood, H. J., and Johnson, T. B., J. Am. Chem. Soc. 54, 3751 (1932). http://dx.doi.org/10.1021/ja01348a04010.1021/ja01348a040Suche in Google Scholar
© 2007 Institute of Chemistry, Slovak Academy of Sciences
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Artikel in diesem Heft
- Step by step towards understanding gold glyconanoparticles as elements of the nanoworld
- Structure—activity relationships for in vitro oxime reactivation of chlorpyrifos-inhibited acetylcholinesterase
- Separation and characterization of products from thermal cracking of individual and mixed polyalkenes
- Mobility of important toxic analytes in urban dust and simulated air filters determined by sequential extraction and GFAAS/ICP-OES methods
- Effect of addition of ameliorative materials on the distribution of As, Cd, Pb, and Zn in extractable soil fractions
- Effect of gamma irradiation on trichromatic values of spices
- Homo- and heteronuclear complexes of a new, vicinal dioxime ligand
- Synthesis of new triphenodithiazine- and indolocarbazolediones of biological interest
- Dielectric relaxation of butyl acrylate—alcohol mixtures using time domain reflectometry
- Ab initio study of small coinage metal telluride clusters AunTem (n, m = 1, 2)
- Binding affinities and spectra of complexes formed by dehydrotetrapyrido[20]annulene and small molecules
- Comparison of spectrophotometric and HPLC methods for determination of lipid peroxidation products in rat brain tissues
- Enantioselective extraction of mandelic acid enantiomers by L-dipentyl tartrate and β-cyclodextrin as binary chiral selectors
- Mechanism of thermal decomposition of cobalt acetate tetrahydrate
- Three-component, one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by bromodimethylsulfonium bromide
