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Synthesis of Novel Acidic Ionic Liquid [BBSA-DBU][HSO4] and Its Catalytic Activities for Synthesis of Pyrazolopyranopyrimidine Derivatives
Corresponding Author(s) : S. Patil
Asian Journal of Chemistry,
Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018
Abstract
A novel Brønsted acid ionic liquid 1,8-bis(butanesulphonic acid)diazobicyclo[5.4.0]undec-7-enium hydrogen sulphate [BBSA-DBU][HSO4] has been synthesized from 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU). The synthesised ionic liquid was characterized by 1H and 13C NMR spectroscopic techniques. The room-temperature derived ionic liquid is highly acidic due to presence of two -SO3H groups and two -HSO4– anions. The ionic liquid [BBSA-DBU][HSO4]showed high catalytic activity (5 mol %) for the synthesis pyrazolpyrano-pyrimidine derivatives with good to excellent yields in short reaction time at 60 °C under solvent-free conditions. Moreover, ionic liquid could be easily recovered and reused at least five times without change in its catalytic activity.
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- N. Gupta, Sonu, G.L. Kad and J. Singh, Catal. Commun., 8, 1323 (2007); https://doi.org/10.1016/j.catcom.2006.11.030.
- R. Sugimura, K. Qiao, D. Tomida and C. Yokoyama, Catal. Commun., 8, 770 (2007); https://doi.org/10.1016/j.catcom.2006.08.049.
- A. Kamal and G. Chouhan, Tetrahedron Lett., 44, 3337 (2003); https://doi.org/10.1016/S0040-4039(03)00580-X.
- X. Liu, Z. Song and H. Wang, Struct. Chem., 20, 509 (2009); https://doi.org/10.1007/s11224-009-9448-6.
- D. Fang, X. Zhou, Z. Ye and Z. Liu, Ind. Eng. Chem. Res., 45, 7982 (2006); https://doi.org/10.1021/ie060365d.
- Y.Y. Wang, X. Gong, Z. Wang and L. Dai, J. Mol. Catal. Chem., 322, 7 (2010); https://doi.org/10.1016/j.molcata.2010.01.011.
- S. Tang, G.A. Baker and H. Zhao, Chem. Soc. Rev., 41, 4030 (2012); https://doi.org/10.1039/c2cs15362a.
- D.B. Zhao, Z. Fei, T.J. Geldbach, R. Scopelliti and P.J. Dyson, J. Am. Chem. Soc., 126, 15876 (2004); https://doi.org/10.1021/ja0463482.
- D. Kuang, S. Uchida, R. Humphry-Baker, S.M. Zakeeruddin and M. Grätzel, Angew. Chem. Int. Ed., 47, 1923 (2008); https://doi.org/10.1002/anie.200705225.
- T. Singh and A. Kumar, J. Phys. Chem., 112, 4079 (2008); https://doi.org/10.1021/jp711711z.
- F. Fu, Y.C. Teo and T.P. Loh, Org. Lett., 8, 5999 (2006); https://doi.org/10.1021/ol062481i.
- P.N. Davey, S.A. Forsyth, H.Q.N. Gunaratne, C. Hardacre, A. McKeown, S. McMath, D.W. Rooney and K.R. Seddon, Green Chem., 7, 224 (2005); https://doi.org/10.1039/B416021E.
- C. Yue, A. Mao, Y. Wei and M. Lu, Catal. Commun., 9, 1571 (2008); https://doi.org/10.1016/j.catcom.2008.01.002.
- Y.O. Sharma and M.S. Degani, J. Mol. Catal. Chem., 277, 215 (2007); https://doi.org/10.1016/j.molcata.2007.07.053.
- L.D. Pinto, J. Dupont, R.F. de Souza and K. Bernardo-Gusmão, Catal. Commun., 9, 135 (2008); https://doi.org/10.1016/j.catcom.2007.05.025.
- M.M. Heravi, F. Mousavizadeh, N. Ghobadi and M. Tajbakhsh, Tetrahedron Lett., 55, 1226 (2014); https://doi.org/10.1016/j.tetlet.2014.01.004.
- G. Nawwar, F. Abdelrazek and R. Swellam, Arch. Pharm., 324, 875 (1991); https://doi.org/10.1002/ardp.2503241110.
- (a) S. Kuo, L. Huang and H. Nakamura, J. Med. Chem., 27, 539 (1984); https://doi.org/10.1021/jm00370a020. (b) L. Huang, M.-J. Hour, C.-M. Teng and S.-C. Kuo, Chem. Pharm. Bull. (Tokyo), 40, 2547 (1992); https://doi.org/10.1248/cpb.40.2547.
- Y.R. Prasad, A.L. Rao, L. Prasoona, K. Murali and P.R. Kumar, Bioorg. Med. Chem. Lett., 15, 5030 (2005); https://doi.org/10.1016/j.bmcl.2005.08.040.
- J.-L. Wang, D. Liu, Z.-J. Zhang, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri and Ziwei Huang, Proc. Natl. Acad. Sci. U.S.A. 97, 7124 (2000); https://doi.org/10.1073/pnas.97.13.7124.
- E. Grivsky, S. Lee, C.W. Sigle, D.S. Duch and C.A. Nichol, J. Med. Chem., 23, 327 (1980); https://doi.org/10.1021/jm00177a025.
- P.J. Chen, A. Yang, Y.F. Gu, X.S. Zhang, K.P. Shao, D.Q. Xue, P. He, T.F. Jiang, Q.R. Zhang and H.M. Liu, Bioorg. Med. Chem. Lett., 24, 2741 (2014); https://doi.org/10.1016/j.bmcl.2014.04.037.
- N.R. Kamdar, D.D. Haveliwala, P.T. Mistry and S.K. Patel, Eur. J. Med. Chem., 45, 5056 (2010); https://doi.org/10.1016/j.ejmech.2010.08.014.
- A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver, D.C. Forbes and J.H. Davis, J. Am. Chem. Soc., 124, 5962 (2002); https://doi.org/10.1021/ja026290w.
References
N. Gupta, Sonu, G.L. Kad and J. Singh, Catal. Commun., 8, 1323 (2007); https://doi.org/10.1016/j.catcom.2006.11.030.
R. Sugimura, K. Qiao, D. Tomida and C. Yokoyama, Catal. Commun., 8, 770 (2007); https://doi.org/10.1016/j.catcom.2006.08.049.
A. Kamal and G. Chouhan, Tetrahedron Lett., 44, 3337 (2003); https://doi.org/10.1016/S0040-4039(03)00580-X.
X. Liu, Z. Song and H. Wang, Struct. Chem., 20, 509 (2009); https://doi.org/10.1007/s11224-009-9448-6.
D. Fang, X. Zhou, Z. Ye and Z. Liu, Ind. Eng. Chem. Res., 45, 7982 (2006); https://doi.org/10.1021/ie060365d.
Y.Y. Wang, X. Gong, Z. Wang and L. Dai, J. Mol. Catal. Chem., 322, 7 (2010); https://doi.org/10.1016/j.molcata.2010.01.011.
S. Tang, G.A. Baker and H. Zhao, Chem. Soc. Rev., 41, 4030 (2012); https://doi.org/10.1039/c2cs15362a.
D.B. Zhao, Z. Fei, T.J. Geldbach, R. Scopelliti and P.J. Dyson, J. Am. Chem. Soc., 126, 15876 (2004); https://doi.org/10.1021/ja0463482.
D. Kuang, S. Uchida, R. Humphry-Baker, S.M. Zakeeruddin and M. Grätzel, Angew. Chem. Int. Ed., 47, 1923 (2008); https://doi.org/10.1002/anie.200705225.
T. Singh and A. Kumar, J. Phys. Chem., 112, 4079 (2008); https://doi.org/10.1021/jp711711z.
F. Fu, Y.C. Teo and T.P. Loh, Org. Lett., 8, 5999 (2006); https://doi.org/10.1021/ol062481i.
P.N. Davey, S.A. Forsyth, H.Q.N. Gunaratne, C. Hardacre, A. McKeown, S. McMath, D.W. Rooney and K.R. Seddon, Green Chem., 7, 224 (2005); https://doi.org/10.1039/B416021E.
C. Yue, A. Mao, Y. Wei and M. Lu, Catal. Commun., 9, 1571 (2008); https://doi.org/10.1016/j.catcom.2008.01.002.
Y.O. Sharma and M.S. Degani, J. Mol. Catal. Chem., 277, 215 (2007); https://doi.org/10.1016/j.molcata.2007.07.053.
L.D. Pinto, J. Dupont, R.F. de Souza and K. Bernardo-Gusmão, Catal. Commun., 9, 135 (2008); https://doi.org/10.1016/j.catcom.2007.05.025.
M.M. Heravi, F. Mousavizadeh, N. Ghobadi and M. Tajbakhsh, Tetrahedron Lett., 55, 1226 (2014); https://doi.org/10.1016/j.tetlet.2014.01.004.
G. Nawwar, F. Abdelrazek and R. Swellam, Arch. Pharm., 324, 875 (1991); https://doi.org/10.1002/ardp.2503241110.
(a) S. Kuo, L. Huang and H. Nakamura, J. Med. Chem., 27, 539 (1984); https://doi.org/10.1021/jm00370a020. (b) L. Huang, M.-J. Hour, C.-M. Teng and S.-C. Kuo, Chem. Pharm. Bull. (Tokyo), 40, 2547 (1992); https://doi.org/10.1248/cpb.40.2547.
Y.R. Prasad, A.L. Rao, L. Prasoona, K. Murali and P.R. Kumar, Bioorg. Med. Chem. Lett., 15, 5030 (2005); https://doi.org/10.1016/j.bmcl.2005.08.040.
J.-L. Wang, D. Liu, Z.-J. Zhang, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri and Ziwei Huang, Proc. Natl. Acad. Sci. U.S.A. 97, 7124 (2000); https://doi.org/10.1073/pnas.97.13.7124.
E. Grivsky, S. Lee, C.W. Sigle, D.S. Duch and C.A. Nichol, J. Med. Chem., 23, 327 (1980); https://doi.org/10.1021/jm00177a025.
P.J. Chen, A. Yang, Y.F. Gu, X.S. Zhang, K.P. Shao, D.Q. Xue, P. He, T.F. Jiang, Q.R. Zhang and H.M. Liu, Bioorg. Med. Chem. Lett., 24, 2741 (2014); https://doi.org/10.1016/j.bmcl.2014.04.037.
N.R. Kamdar, D.D. Haveliwala, P.T. Mistry and S.K. Patel, Eur. J. Med. Chem., 45, 5056 (2010); https://doi.org/10.1016/j.ejmech.2010.08.014.
A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver, D.C. Forbes and J.H. Davis, J. Am. Chem. Soc., 124, 5962 (2002); https://doi.org/10.1021/ja026290w.