Copyright (c) 2017 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Microwave Promoted Y(NO3)3·6H2O Catalyzed Biginelli Synthesis of Dihydropyrimidin-2-ones
Corresponding Author(s) : M.A. Mondal
Asian Journal of Chemistry,
Vol. 29 No. 3 (2017): Vol 29 Issue 3
Abstract
Biginelli synthesis of 3,4-dihydropyrimidinones from aldehydes, b-keto ester and urea using yttrium nitrate hexahydrate, as an efficient catalyst are demonstrated under microwave condition. This method offers significant advantages, such as high yields, short reaction times, easy isolation and mild reaction conditions. We have also investigated mechanism of Y(NO3)3 catalyzed 3,4-dihydropyrimidinones synthesis and identified the key intermediate benzal-bisurea by LC-MS.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- C.O. Kappe, K. Peters and E.-M. Peters, J. Org. Chem., 62, 3109 (1997).
- D. Nagarathnam, S.W. Miao, B. Lagu, G. Chiu, J. Fang, T.G. Murali Dhar, J. Zhang, S. Tyagarajan, M.R. Marzabadi, F. Zhang, W.C. Wong, W. Sun, D. Tian, J.M. Wetzel, C. Forray, R.S.L. Chang, T.P. Broten, R.W. Ransom, T.W. Schorn, T.B. Chen, S. O’Malley, P. Kling, K. Schneck, R. Bendesky, C.M. Harrell, K.P. Vyas and C. Gluchowski, J. Med. Chem., 42, 4764 (1999).
- M. Brands, R. Endermann, R. Gahlmann, J. Krüger and S. Raddatz, Bioorg. Med. Chem. Lett., 13, 241 (2003).
- J.P. Wan and Y. Pan, Mini Rev. Med. Chem., 12, 337 (2012).
- F. Bossert and W. Vater, Med. Res. Rev., 9, 291 (1989).
- C.O. Kappe, Acc. Chem. Res., 33, 879 (2000).
- J.S.S. Suresh, ARKIVOC, 57 (2012).
- A. de Fátima, T.C. Braga, L.S. Neto, B.S. Terra, B.G.F. Oliveira, D.L. da Silva and L.V. Modolo, J. Adv. Res., 6, 363 (2015).
- C.O. Kappe, Tetrahedron, 49, 6937 (1993).
- P. Biginelli, Ber. Dtsch. Chem. Ges., 24, 2962 (1891).
- E.H. Hu, D.R. Sidler and U.-H. Dolling, J. Org. Chem., 63, 3454 (1998).
- N.-Y. Fu, Y.-F. Yuan, Z. Cao, S.-W. Wang, J.-T. Wang and C. Peppe, Tetrahedron, 58, 4801 (2002).
- J. Lu and Y. Bai, Synthesis, 466 (2002).
- J. Lu, Y.-J. Bai, Y.-H. Guo, Z.-J. Wang and H.-R. Ma, Chin. J. Chem., 20, 681 (2002).
- M.M. Alam, R. Varala and S.A. Adapa, Tetrahedron Lett., 44, 5115 (2003).
- I. Cepanec, M. Litvic, A. Bartolincic and M. Lovric, Tetrahedron, 61, 4275 (2005).
- S.V. Ryabukhin, A.S. Plaskon, E.N. Ostapchuk, D.M. Volochnyuk and A.A. Tolmachev, Synthesis, 417 (2007).
- D. Song, R. Wang, Y. Chen, S. Zhang, C. Liu and G. Luo, React. Kinet. Catal. Lett., 95, 385 (2008).
- S.K. De and R.A. Gibbs, Synthesis, 1748 (2005).
- A. Debache, R. Boulcina, R. Tafer, A. Belfaitah, S. Rhouati and B. Carboni, Chin. J. Chem., 26, 2112 (2008).
- B.A. Dar, P. Patidar, S. Kumar, M.A. Wagay, A.K. Sahoo, P.R. Sharma, S. Pandey, M. Sharma and B. Singh, J. Chem. Sci., 125, 545 (2013).
- S. Nagarajan, T.M. Shaikh and E. Kandasamy, J. Chem. Sci., 127, 1539 (2015).
- A.N. Dadhania, V.K. Patel and D.K. Raval, J. Chem. Sci., 124, 921 (2012).
- D.V. Jawale, U.R. Pratap, A.A. Mulay, J.R. Mali and R.A. Mane, J. Chem. Sci., 123, 645 (2011).
- S.K. Prajapti, K.K. Gupta and B.N. Babu, J. Chem. Sci., 127, 1047 (2015).
- C. James and L.A. Pratt, J. Am. Chem. Soc., 32, 873 (1910).
- N.S. Nandurkar, M.J. Bhanushali, M.D. Bhor and B.M. Bhanage, J. Mol. Catal. Chem., 271, 14 (2007).
- K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 55, 3784 (1933).
- F. Sweet and J.D. Fissekis, J. Am. Chem. Soc., 95, 8741 (1973).
- M. Das, Inorg. Chim. Acta, 83, L1 (1984).
References
C.O. Kappe, K. Peters and E.-M. Peters, J. Org. Chem., 62, 3109 (1997).
D. Nagarathnam, S.W. Miao, B. Lagu, G. Chiu, J. Fang, T.G. Murali Dhar, J. Zhang, S. Tyagarajan, M.R. Marzabadi, F. Zhang, W.C. Wong, W. Sun, D. Tian, J.M. Wetzel, C. Forray, R.S.L. Chang, T.P. Broten, R.W. Ransom, T.W. Schorn, T.B. Chen, S. O’Malley, P. Kling, K. Schneck, R. Bendesky, C.M. Harrell, K.P. Vyas and C. Gluchowski, J. Med. Chem., 42, 4764 (1999).
M. Brands, R. Endermann, R. Gahlmann, J. Krüger and S. Raddatz, Bioorg. Med. Chem. Lett., 13, 241 (2003).
J.P. Wan and Y. Pan, Mini Rev. Med. Chem., 12, 337 (2012).
F. Bossert and W. Vater, Med. Res. Rev., 9, 291 (1989).
C.O. Kappe, Acc. Chem. Res., 33, 879 (2000).
J.S.S. Suresh, ARKIVOC, 57 (2012).
A. de Fátima, T.C. Braga, L.S. Neto, B.S. Terra, B.G.F. Oliveira, D.L. da Silva and L.V. Modolo, J. Adv. Res., 6, 363 (2015).
C.O. Kappe, Tetrahedron, 49, 6937 (1993).
P. Biginelli, Ber. Dtsch. Chem. Ges., 24, 2962 (1891).
E.H. Hu, D.R. Sidler and U.-H. Dolling, J. Org. Chem., 63, 3454 (1998).
N.-Y. Fu, Y.-F. Yuan, Z. Cao, S.-W. Wang, J.-T. Wang and C. Peppe, Tetrahedron, 58, 4801 (2002).
J. Lu and Y. Bai, Synthesis, 466 (2002).
J. Lu, Y.-J. Bai, Y.-H. Guo, Z.-J. Wang and H.-R. Ma, Chin. J. Chem., 20, 681 (2002).
M.M. Alam, R. Varala and S.A. Adapa, Tetrahedron Lett., 44, 5115 (2003).
I. Cepanec, M. Litvic, A. Bartolincic and M. Lovric, Tetrahedron, 61, 4275 (2005).
S.V. Ryabukhin, A.S. Plaskon, E.N. Ostapchuk, D.M. Volochnyuk and A.A. Tolmachev, Synthesis, 417 (2007).
D. Song, R. Wang, Y. Chen, S. Zhang, C. Liu and G. Luo, React. Kinet. Catal. Lett., 95, 385 (2008).
S.K. De and R.A. Gibbs, Synthesis, 1748 (2005).
A. Debache, R. Boulcina, R. Tafer, A. Belfaitah, S. Rhouati and B. Carboni, Chin. J. Chem., 26, 2112 (2008).
B.A. Dar, P. Patidar, S. Kumar, M.A. Wagay, A.K. Sahoo, P.R. Sharma, S. Pandey, M. Sharma and B. Singh, J. Chem. Sci., 125, 545 (2013).
S. Nagarajan, T.M. Shaikh and E. Kandasamy, J. Chem. Sci., 127, 1539 (2015).
A.N. Dadhania, V.K. Patel and D.K. Raval, J. Chem. Sci., 124, 921 (2012).
D.V. Jawale, U.R. Pratap, A.A. Mulay, J.R. Mali and R.A. Mane, J. Chem. Sci., 123, 645 (2011).
S.K. Prajapti, K.K. Gupta and B.N. Babu, J. Chem. Sci., 127, 1047 (2015).
C. James and L.A. Pratt, J. Am. Chem. Soc., 32, 873 (1910).
N.S. Nandurkar, M.J. Bhanushali, M.D. Bhor and B.M. Bhanage, J. Mol. Catal. Chem., 271, 14 (2007).
K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 55, 3784 (1933).
F. Sweet and J.D. Fissekis, J. Am. Chem. Soc., 95, 8741 (1973).
M. Das, Inorg. Chim. Acta, 83, L1 (1984).