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Three-component, one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by bromodimethylsulfonium bromide

  • A. Shaabani EMAIL logo and A. Maleki
Published/Copyright: August 1, 2007
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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)87971-0Search 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.2006.01.007Search 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)00280-0Search 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)00455-6Search 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/jo000711fSearch 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/jo9919052Search 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)01645-2Search 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)01603-3Search 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/b102565cSearch 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)00424-4Search in Google Scholar

[11] Kappe, C. O., Kumar, D., and Varma, R. S., Synthesis 1999, 1799. 10.1055/s-1999-3592Search 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/jo005512aSearch in Google Scholar

[13] Yadav, J. S., Reddy, B. V. S., Reddy, E. J., and Ramalingam, T., J. Chem. Res., Synop. 2000, 354. 10.3184/030823400103167633Search 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/jo970846uSearch 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)02612-6Search 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-1987-05-1189Search 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/jo00286a020Search 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-XSearch in Google Scholar

[19] Furukawa, N., Inoue, T., Aida, T., and Oae, S., J. Chem. Soc., Chem. Commun. 1973, 212a. 10.1039/c3973000212aSearch in Google Scholar

[20] Olah, G. A., Yashwant, D. V., Massoud, A., and Suryaprakash, G. K., Synthesis 1979, 720. 10.1055/s-1979-28811Search 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.200300685Search 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.2005.05.042Search 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.2004.12.070Search 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.2005.10.015Search 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.2006.05.101Search 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.2006.04.059Search in Google Scholar

[27] Das, B., Ramu, R., Ravikanth, B., and Reddy, K. R., Synthesis 2006, 1419. 10.1055/s-2006-926421Search 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.2004.01.154Search in Google Scholar

[29] Shaabani, A., Bazgir, A., and Arab-Ameri, S., Phosphorus Sulfur 179, 2169 (2004). http://dx.doi.org/10.1080/1042650049047481510.1080/10426500490474815Search 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/s10562-004-3451-8Search 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.2005.08.101Search 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/ja01348a040Search in Google Scholar

Published Online: 2007-8-1
Published in Print: 2007-8-1

© 2007 Institute of Chemistry, Slovak Academy of Sciences

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