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Microwave-Assisted Efficient Synthesis of Spiropyridine Derivatives via Catalyst- and Solvent-Free One Pot Four Component Reaction
Corresponding Author(s) : Debajyoti Bhuyan
Asian Journal of Chemistry,
Vol. 33 No. 1 (2021): Vol 33 Issue 1
Abstract
A microwave-assisted, one-pot four-component reaction strategy has been developed for the synthesis of some novel spiropyridine derivatives from 1,3-dimethyl barbituric acid, chalcone, aromatic aldehyde and ammonium acetate under catalyst- and solvent-free conditions.
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- N.B. Patel, S.N. Agravat and F.M. Shaikh, Med. Chem. Res., 20, 1033(2011); https://doi.org/10.1007 s00044-010-9440-0
- N.B. Patel and S.N. Agravat, Chem. Heterocycl. Compd., 45, 1343(2009); https://doi.org/10.1007/s10593-010-0432-2
- E.G. Paronikyan, A.S. Noravyan, I.A. Dzhagatspanyan, I.M. Nazaryan and R.G. Paronikyan, Pharm. Chem. J., 36, 465 (2002); https://doi.org/10.1023/A:1021836504036
- M.G. Mamolo, D. Zampieri, V. Falagiani, L. Vio, M. Fermeglia, M.Ferrone, S. Pricl, E. Banfi and G. Scialino, ARKIVOC, 231 (2004); https://doi.org/10.3998/ark.5550190.0005.521
- S.X. Cai, B. Nguyen, S. Jia, J. Herich, J. Guastella, S. Reddy, B. Tseng, J. Drewe and S. Kasibhatla, J. Med. Chem., 46, 2474 (2003); https://doi.org/10.1021/jm0205200
- D. Geffken, R. Soliman, F.S.G. Soliman, M.M. Abdel-Khalek and D.A.E. Issa, J. Med. Chem. Res., 20, 408 (2011);https://doi.org/10.1007/s00044-010-9328-z
- P.D. Bouzard, P.D. Cesare, C. Dussy, J.P. Jacquet and A. Jaegly, J.Heterocycl. Chem., 29, 985 (1993);https://doi.org/10.1002/jhet.5570290453
- A.E. Tschitschibabin, J. Prakt. Chem., 107, 122 (1924); https://doi.org/10.1002/prac.19241070110
- A.H. Corwin, Heterocyclic Compounds, vol. 1, p. 309 (1950).
- H. Bönnemann, Angew. Chem. Int. Ed. Engl., 17, 505 (1978); https://doi.org/10.1002/anie.197805051
- A. Hantzsch, Chem. Ber., 14, 1637 (1881); https://doi.org/10.1002/cber.18810140214
- L. Gattermann and A. Skita, Chem. Ber., 49, 494 (1916); https://doi.org/10.1002/cber.19160490155
- M. Kidwai, S. Saxena, R. Mohan and R. Venkataramanan, J. Chem. Soc., Perkin Trans. I, 1845 (2002);https://doi.org/10.1039/B205539M
- L. Ohberg and J. Westman, Synlett, 1296 (2001); https://doi.org/10.1055/s-2001-16043
- M.C. Bagley, R. Lunn and X. Xiong, Tetrahedron Lett., 43, 8331 (2002); https://doi.org/10.1016/S0040-4039(02)01975-5
- X. Yang, Y. Cheng, F. Zhao, Y. Li, Y. Ding, Y. Liang, F. Gan and D. Dong,Tetrahedron, 67, 8343 (2011);https://doi.org/10.1016/j.tet.2011.08.066
- G. Yin, Q. Liu, J. Ma and N. She, Green Chem., 14, 1796 (2012); https://doi.org/10.1039/c2gc35243e
- B. Dai, Y. Duan, X. Liu, L. Song, M. Zhang, W. Cao, S. Zhu, H. Deng and M. Shao, J. Fluor. Chem., 133, 127 (2012);https://doi.org/10.1016/j.jfluchem.2011.09.006
- G.W.V. Cave and C.L. Raston, Chem. Commun., 2199 (2000); https://doi.org/10.1039/B007431O
- H. Kurihara and H. Mishima, J. Heterocycl. Chem., 14, 1077 (1977); https://doi.org/10.1002/jhet.5570140628
- P. Molina, A. Pastor and M.J. Vilaplana, J. Org. Chem., 61, 8094 (1996); https://doi.org/10.1021/jo960940v
- I.W. Davies, J.-F. Marcoux, E.G. Corley, M. Journet, D.-W. Cai, M. Palucki, J. Wu, R.D. Larsen, K. Rossen, P.J. Pye, L. DiMichele, P. Dormer and P.J. Reider, J. Org. Chem., 65, 8415 (2000); https://doi.org/10.1021/jo000870z
- S.A. Al-Issa, Molecules, 17, 10902 (2012); https://doi.org/10.3390/molecules170910902
- M.M. Heravi, K.H. Bakhtiari, Z. Daroogheha and F.F. Bamoharram, Catal. Commun., 8, 1991 (2007);https://doi.org/10.1016/j.catcom.2007.03.028
References
N.B. Patel, S.N. Agravat and F.M. Shaikh, Med. Chem. Res., 20, 1033(2011); https://doi.org/10.1007 s00044-010-9440-0
N.B. Patel and S.N. Agravat, Chem. Heterocycl. Compd., 45, 1343(2009); https://doi.org/10.1007/s10593-010-0432-2
E.G. Paronikyan, A.S. Noravyan, I.A. Dzhagatspanyan, I.M. Nazaryan and R.G. Paronikyan, Pharm. Chem. J., 36, 465 (2002); https://doi.org/10.1023/A:1021836504036
M.G. Mamolo, D. Zampieri, V. Falagiani, L. Vio, M. Fermeglia, M.Ferrone, S. Pricl, E. Banfi and G. Scialino, ARKIVOC, 231 (2004); https://doi.org/10.3998/ark.5550190.0005.521
S.X. Cai, B. Nguyen, S. Jia, J. Herich, J. Guastella, S. Reddy, B. Tseng, J. Drewe and S. Kasibhatla, J. Med. Chem., 46, 2474 (2003); https://doi.org/10.1021/jm0205200
D. Geffken, R. Soliman, F.S.G. Soliman, M.M. Abdel-Khalek and D.A.E. Issa, J. Med. Chem. Res., 20, 408 (2011);https://doi.org/10.1007/s00044-010-9328-z
P.D. Bouzard, P.D. Cesare, C. Dussy, J.P. Jacquet and A. Jaegly, J.Heterocycl. Chem., 29, 985 (1993);https://doi.org/10.1002/jhet.5570290453
A.E. Tschitschibabin, J. Prakt. Chem., 107, 122 (1924); https://doi.org/10.1002/prac.19241070110
A.H. Corwin, Heterocyclic Compounds, vol. 1, p. 309 (1950).
H. Bönnemann, Angew. Chem. Int. Ed. Engl., 17, 505 (1978); https://doi.org/10.1002/anie.197805051
A. Hantzsch, Chem. Ber., 14, 1637 (1881); https://doi.org/10.1002/cber.18810140214
L. Gattermann and A. Skita, Chem. Ber., 49, 494 (1916); https://doi.org/10.1002/cber.19160490155
M. Kidwai, S. Saxena, R. Mohan and R. Venkataramanan, J. Chem. Soc., Perkin Trans. I, 1845 (2002);https://doi.org/10.1039/B205539M
L. Ohberg and J. Westman, Synlett, 1296 (2001); https://doi.org/10.1055/s-2001-16043
M.C. Bagley, R. Lunn and X. Xiong, Tetrahedron Lett., 43, 8331 (2002); https://doi.org/10.1016/S0040-4039(02)01975-5
X. Yang, Y. Cheng, F. Zhao, Y. Li, Y. Ding, Y. Liang, F. Gan and D. Dong,Tetrahedron, 67, 8343 (2011);https://doi.org/10.1016/j.tet.2011.08.066
G. Yin, Q. Liu, J. Ma and N. She, Green Chem., 14, 1796 (2012); https://doi.org/10.1039/c2gc35243e
B. Dai, Y. Duan, X. Liu, L. Song, M. Zhang, W. Cao, S. Zhu, H. Deng and M. Shao, J. Fluor. Chem., 133, 127 (2012);https://doi.org/10.1016/j.jfluchem.2011.09.006
G.W.V. Cave and C.L. Raston, Chem. Commun., 2199 (2000); https://doi.org/10.1039/B007431O
H. Kurihara and H. Mishima, J. Heterocycl. Chem., 14, 1077 (1977); https://doi.org/10.1002/jhet.5570140628
P. Molina, A. Pastor and M.J. Vilaplana, J. Org. Chem., 61, 8094 (1996); https://doi.org/10.1021/jo960940v
I.W. Davies, J.-F. Marcoux, E.G. Corley, M. Journet, D.-W. Cai, M. Palucki, J. Wu, R.D. Larsen, K. Rossen, P.J. Pye, L. DiMichele, P. Dormer and P.J. Reider, J. Org. Chem., 65, 8415 (2000); https://doi.org/10.1021/jo000870z
S.A. Al-Issa, Molecules, 17, 10902 (2012); https://doi.org/10.3390/molecules170910902
M.M. Heravi, K.H. Bakhtiari, Z. Daroogheha and F.F. Bamoharram, Catal. Commun., 8, 1991 (2007);https://doi.org/10.1016/j.catcom.2007.03.028