How to cite this paper
Albadi, J & Mansournezhad, A. (2014). Poly(4-vinylpyridine) efficiently catalyzed one-pot four-component synthesis of pyrano[2,3-c]pyrazoles.Current Chemistry Letters, 3(4), 221-227.
Refrences
1 Balme, G., Bossharth, E., and Monteiro, N. (2003) Pd-Assisted multicomponent synthesis of heterocycles. Eur. J. Org. Chem., 4101-4111.
2 Nair, V., Vinod, A. U., and Rajesh, C. (2001) A novel synthesis of 2-aminopyrroles using a three-component Reaction. J. Org. Chem., 66, 4427-4429.
3 Domling, A., and Ugi, I. (2000) Multicomponent reactions with isocyanides. Angew. Chem. Int. Ed., 39, 3168-3210.
4 Singh, K., Singh, J., and Singh, H. (1996) A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles. Tetrahedron., 52, 14273-14280.
5 Bonsignore, B., Loy, G., Secci, D., and Calignano, A. (1993). Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives. Eur. J. Med. Chem., 28, 517-520.
6 Mistry, P. T., Kamdar, N. R., Haveliwala,. D. D., and Patel, S. K. (2012) Synthesis, characterization, and in vitro biological studies of some novel pyran fused pyrimidone derivatives. J. Heterocyclic. Chem., 49, 349-357.
7 Kuo, S. C, Huang, L. J., and Nakamura, H. (1984) Synthesis and analgesic and antiinflammatory activities of 3,4-dimethylpyrano[2,3-c]pyrazol-6-one derivatives. Eur. J. Med. Chem., 27. 539-534.
8 Wamhoff, H., Kroth, E., and Strauch, K. (1993) Dihalogentriphenylphosphorane in der heterocycle synthese; 271:heterokondensierte 1,2,4-Triazolo[1,5-c]pyrimidine aus enaminonitrilen via O-Ethylformimide. Synthesis., 11, 1129-1132.
9 Armetso, D., Horspool, W. M., Martin, N., Ramos, A., and Seaone, C. (1989) Synthesis of cyclobutenes by the novel photochemical ring contraction of 4-substituted 2-amino-3,5-dicyano-6-phenyl-4H-pyrans. J. Org. Chem., 54, 3069-3072.
10 Jin, T. S., Wang, A. Q., Cheng, Z. L., Zhang, J. S., and Li, S. (2005) A Clean and simple synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole in water. Synth. Commun., 35, 137-143.
11 Shestopalov, A. M., Emeliyanova, Y. M., Shestopalov, A. A., Rodinovskaya, L. A., Niazimbetova, Z. I., and Evans, D. H. ( 2002) One-Step Synthesis of Substituted 6-Amino-5-cyanospiro-4-(piperidine-4‘)- 2H,4H-dihydropyrazolo[3,4-b]pyrans. Org. Letts., 4, 423-425.
12 Vasuki, G., and Kandhasamy, K. (2008) Rapid four-component reactions in water: synthesis of pyranopyrazoles. Tetrahedron Letters, 49, 5636-5638.
13 El-Assaly, S. A. (2011) A simple and clean method for four-component synthesis of pyrano[2,3-c]pyrazole derivatives. Der Pharma Chem., 3, 81-86.
14 Kiyani, H., Samimi, H., Ghorbani. F., and Esmaieli, F. ( 2013) One-pot, four-component synthesis of pyrano[2,3-c]pyrazoles catalyzed by sodium benzoate in aqueous medium. Curr. Chem. Lett., 2, 197-206.
15 Ebrahimi, J., Mohammadi, A., Pakjoo, V., Bahramzade, E., and Habibi, A. (2012) Highly efficient solvent-free synthesis of pyranopyrazoles by a Br?nsted-acidic ionic liquid as a green and reusable catalyst. J. Chem. Sci.,124, 1013-1017.
16 Gogoi, S., and Zhao, C. G. (2009) Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles. Tetrahedron Letters., 50, 2252-2255.
17 Azzam , S. H. S., and Pasha, M. A. (2012) Simple and efficient protocol for the synthesis of novel dihydro-1H-pyrano[2,3-c]pyrazol-6-ones via a one-pot four-component reaction. Tetrahedron Letters., 53, 6834-6837.
18 Jin, T. S., Wang, A. Q, Cheng, Z. L, Zhang, J. S., and Li, T. S. (2005) A clean and simple synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole in water. Synth. Commun., 35, 137-143.
19 Wang, X. S., Shi, D. Q., Tu, S. J., Yao, C. S., and Wang ,Y. C. (2003) Synthesis and crystal structure of 3-methyl-5-cyano-6-amino-1-phenyl-4-(3,4-dimethoxyphenyl)-1,4-dihydropyrano[2,3-c]pyrazole. Chin. J. Struct. Chem., 22, 331-335.
20 Hasaninejad, A., Shekouhy, M., Golzar, N., Zare, A., and Doroodmand, M. M. (2011). Silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO): A highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4H benzo[b]pyran derivatives. Appl. Catal. A: Gen., 402 ,11-22.
21 Albadi, J., Mansournezhad, A., and Derakhshandeh, Z. (2013) CuO-CeO2 nanocomposite: A highly efficient recyclable catalyst for the multicomponent synthesis of 4H-benzo[b]pyran derivatives. Chin. Chem. Lett., 24, 821-824.
22 Shi, D., Mou, J., Zhuang, Q, Niu, L., Wu, N., and Wang, X. (2004) Three-component one-pot Synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives in aqueous media. Synth. Commun., 34, 4557-4563.
23 Khurana, J. M, Nand, B., and Kumar, S. (2011) Rapid synthesis of polyfunctionalized pyrano[2,3-c]pyrazoles via multicomponent condensation in room-temperature liquids. Synth. Comm., 41, 405-410.
24 Guo, S. B, Wang, S. X., and Li, J. T. (2010). D, L-Proline-catalyzed one-pot synthesis of pyrans and pyrano[2,3-c]pyrazole derivatives by a grinding method under solvent-free conditions. Synth. Commun., 37, 2111-2117.
25 Vasuki, G., and Kandhasamy, K. (2008) Rapid four-component reactions in water: Synthesis of pyranopyrazoles. Tetrahedron Letters., 49, 5636-5638.
26 Khurana, J. M., and Chaudhary, A. (2012) Efficient and green synthesis of 4H-pyrans and 4Hpyrano[2,3-c]pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions. Green Chem. Lett. Rev., 5, 633-638.
27 Chavan, H. V., Babar, S. B., Hoval, R. U., and Bandgar, B. P. (2011) Rapid one-pot, four component synthesis of pyranopyrazoles using heteropolyacid under solvent-free condition. Bull. Korean. Chem. Soc., 32, 3963-3966.
28 Reddy, M. B. M., Jayashankara, V. P., and Pasha, M. A. (2010) Glycine-catalyzed efficient synthesis of pyranopyrazoles via one-pot multicomponent reaction. Synth. Commun., 40, 2930-2934.
29 Wu, M., Feng, Q., Wan, D., and Ma, J. ( 2013). CTACl as catalyst for four-component one-pot synthesis of pyranopyrazole derivatives in aqueous medium. Synth. Commun., 43 ,1721-1726.
30 Shinde, P. V, Gujar, J. B., Shingate, B. B., and Shingare, M. S. (2012). Silica in water: A potentially valuable reaction medium for the synthesis of pyrano[2,3-c]pyrazoles. Bull. Korean Chem. Soc., 33, 1345-1348.
31 Albadi, J., Mansournezhad, A., and Darvishi-Paduk, M. (2013) Poly(4-vinylpyridine): As a green, efficient and commercial available basic catalyst for the synthesis of chromene derivatives. Chin. Chem. Lett., 24, 208-210.
32 Albadi, J., Fadaeian, M., and Akbari, Balout-Bangan, F. (2013). Efficient synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by poly(4-vinylpyridine) as a green and heterogeneous recyclable basic catalyst under solvent-free condtions. (2013). Iran. J. Org. Chem., 5, 1089-1092.
2 Nair, V., Vinod, A. U., and Rajesh, C. (2001) A novel synthesis of 2-aminopyrroles using a three-component Reaction. J. Org. Chem., 66, 4427-4429.
3 Domling, A., and Ugi, I. (2000) Multicomponent reactions with isocyanides. Angew. Chem. Int. Ed., 39, 3168-3210.
4 Singh, K., Singh, J., and Singh, H. (1996) A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles. Tetrahedron., 52, 14273-14280.
5 Bonsignore, B., Loy, G., Secci, D., and Calignano, A. (1993). Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives. Eur. J. Med. Chem., 28, 517-520.
6 Mistry, P. T., Kamdar, N. R., Haveliwala,. D. D., and Patel, S. K. (2012) Synthesis, characterization, and in vitro biological studies of some novel pyran fused pyrimidone derivatives. J. Heterocyclic. Chem., 49, 349-357.
7 Kuo, S. C, Huang, L. J., and Nakamura, H. (1984) Synthesis and analgesic and antiinflammatory activities of 3,4-dimethylpyrano[2,3-c]pyrazol-6-one derivatives. Eur. J. Med. Chem., 27. 539-534.
8 Wamhoff, H., Kroth, E., and Strauch, K. (1993) Dihalogentriphenylphosphorane in der heterocycle synthese; 271:heterokondensierte 1,2,4-Triazolo[1,5-c]pyrimidine aus enaminonitrilen via O-Ethylformimide. Synthesis., 11, 1129-1132.
9 Armetso, D., Horspool, W. M., Martin, N., Ramos, A., and Seaone, C. (1989) Synthesis of cyclobutenes by the novel photochemical ring contraction of 4-substituted 2-amino-3,5-dicyano-6-phenyl-4H-pyrans. J. Org. Chem., 54, 3069-3072.
10 Jin, T. S., Wang, A. Q., Cheng, Z. L., Zhang, J. S., and Li, S. (2005) A Clean and simple synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole in water. Synth. Commun., 35, 137-143.
11 Shestopalov, A. M., Emeliyanova, Y. M., Shestopalov, A. A., Rodinovskaya, L. A., Niazimbetova, Z. I., and Evans, D. H. ( 2002) One-Step Synthesis of Substituted 6-Amino-5-cyanospiro-4-(piperidine-4‘)- 2H,4H-dihydropyrazolo[3,4-b]pyrans. Org. Letts., 4, 423-425.
12 Vasuki, G., and Kandhasamy, K. (2008) Rapid four-component reactions in water: synthesis of pyranopyrazoles. Tetrahedron Letters, 49, 5636-5638.
13 El-Assaly, S. A. (2011) A simple and clean method for four-component synthesis of pyrano[2,3-c]pyrazole derivatives. Der Pharma Chem., 3, 81-86.
14 Kiyani, H., Samimi, H., Ghorbani. F., and Esmaieli, F. ( 2013) One-pot, four-component synthesis of pyrano[2,3-c]pyrazoles catalyzed by sodium benzoate in aqueous medium. Curr. Chem. Lett., 2, 197-206.
15 Ebrahimi, J., Mohammadi, A., Pakjoo, V., Bahramzade, E., and Habibi, A. (2012) Highly efficient solvent-free synthesis of pyranopyrazoles by a Br?nsted-acidic ionic liquid as a green and reusable catalyst. J. Chem. Sci.,124, 1013-1017.
16 Gogoi, S., and Zhao, C. G. (2009) Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles. Tetrahedron Letters., 50, 2252-2255.
17 Azzam , S. H. S., and Pasha, M. A. (2012) Simple and efficient protocol for the synthesis of novel dihydro-1H-pyrano[2,3-c]pyrazol-6-ones via a one-pot four-component reaction. Tetrahedron Letters., 53, 6834-6837.
18 Jin, T. S., Wang, A. Q, Cheng, Z. L, Zhang, J. S., and Li, T. S. (2005) A clean and simple synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole in water. Synth. Commun., 35, 137-143.
19 Wang, X. S., Shi, D. Q., Tu, S. J., Yao, C. S., and Wang ,Y. C. (2003) Synthesis and crystal structure of 3-methyl-5-cyano-6-amino-1-phenyl-4-(3,4-dimethoxyphenyl)-1,4-dihydropyrano[2,3-c]pyrazole. Chin. J. Struct. Chem., 22, 331-335.
20 Hasaninejad, A., Shekouhy, M., Golzar, N., Zare, A., and Doroodmand, M. M. (2011). Silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO): A highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4H benzo[b]pyran derivatives. Appl. Catal. A: Gen., 402 ,11-22.
21 Albadi, J., Mansournezhad, A., and Derakhshandeh, Z. (2013) CuO-CeO2 nanocomposite: A highly efficient recyclable catalyst for the multicomponent synthesis of 4H-benzo[b]pyran derivatives. Chin. Chem. Lett., 24, 821-824.
22 Shi, D., Mou, J., Zhuang, Q, Niu, L., Wu, N., and Wang, X. (2004) Three-component one-pot Synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives in aqueous media. Synth. Commun., 34, 4557-4563.
23 Khurana, J. M, Nand, B., and Kumar, S. (2011) Rapid synthesis of polyfunctionalized pyrano[2,3-c]pyrazoles via multicomponent condensation in room-temperature liquids. Synth. Comm., 41, 405-410.
24 Guo, S. B, Wang, S. X., and Li, J. T. (2010). D, L-Proline-catalyzed one-pot synthesis of pyrans and pyrano[2,3-c]pyrazole derivatives by a grinding method under solvent-free conditions. Synth. Commun., 37, 2111-2117.
25 Vasuki, G., and Kandhasamy, K. (2008) Rapid four-component reactions in water: Synthesis of pyranopyrazoles. Tetrahedron Letters., 49, 5636-5638.
26 Khurana, J. M., and Chaudhary, A. (2012) Efficient and green synthesis of 4H-pyrans and 4Hpyrano[2,3-c]pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions. Green Chem. Lett. Rev., 5, 633-638.
27 Chavan, H. V., Babar, S. B., Hoval, R. U., and Bandgar, B. P. (2011) Rapid one-pot, four component synthesis of pyranopyrazoles using heteropolyacid under solvent-free condition. Bull. Korean. Chem. Soc., 32, 3963-3966.
28 Reddy, M. B. M., Jayashankara, V. P., and Pasha, M. A. (2010) Glycine-catalyzed efficient synthesis of pyranopyrazoles via one-pot multicomponent reaction. Synth. Commun., 40, 2930-2934.
29 Wu, M., Feng, Q., Wan, D., and Ma, J. ( 2013). CTACl as catalyst for four-component one-pot synthesis of pyranopyrazole derivatives in aqueous medium. Synth. Commun., 43 ,1721-1726.
30 Shinde, P. V, Gujar, J. B., Shingate, B. B., and Shingare, M. S. (2012). Silica in water: A potentially valuable reaction medium for the synthesis of pyrano[2,3-c]pyrazoles. Bull. Korean Chem. Soc., 33, 1345-1348.
31 Albadi, J., Mansournezhad, A., and Darvishi-Paduk, M. (2013) Poly(4-vinylpyridine): As a green, efficient and commercial available basic catalyst for the synthesis of chromene derivatives. Chin. Chem. Lett., 24, 208-210.
32 Albadi, J., Fadaeian, M., and Akbari, Balout-Bangan, F. (2013). Efficient synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by poly(4-vinylpyridine) as a green and heterogeneous recyclable basic catalyst under solvent-free condtions. (2013). Iran. J. Org. Chem., 5, 1089-1092.