How to cite this paper
Kiyani, H., Samimi, H., Ghorbani, F & Esmaieli, S. (2013). One-pot, four-component synthesis of pyrano[2,3-c]pyrazoles catalyzed by sodium benzoate in aqueous medium.Current Chemistry Letters, 2(4), 197-206.
Refrences
1 (a) Mistry, P. T.; Kamdar, N. R.; Haveliwala, D. D.; Patel, S. K. (2012), Synthesis, Characterization, and In Vitro Biological Studies of Some Novel Pyran Fused Pyrimidone Derivatives. J. Heterocyclic Chem. 49, 349-357; (b) Mandour, A. H.; El-Sawy, E. R.; Ebaid, M. S.; Hassan, S. M. (2012), Synthesis and potential biological activity of some novel 3-[(N-substitutedindol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles and 3,6-diamino-4-(N-substitutedindol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles. Acta Pharm. 62, 15-30.
2 Kuo, S. C.; Huang, L. J.; Nakamura, H. (1984), Studies on heterocyclic compounds. 6. Synthesis and analgesic and antiinflammatory activities of 3,4-dimethyl-pyra- 2,3-c]pyrazol-6-one derivatives. J. Med. Chem. 27, 539-544.
3 Ahluwalia, V. K.; Dahiya, A.; Garg, V. (1997), Reaction of 5-amino-4-formyl-3-methyl(or phenyl)-1-phenyl-1H-pyrazoles with active methylene compounds: Synthesis of fused heterocyclic rings. Indian J. Chem. 36B, 88-90.
4 Wang, J. L.; Liu, D.; Zheng, Z. J.; Shan, S.; Han, X.; Srinivasula, S. M.; Croce, C. M.; Alnemri, E. S.; Huang, Z. (2009), Structure-based discovery of an organic compound that bind Bc1-2 protein and induces apoptosis of tumor cells. Proc. Natl. Acad. Sci. U.S.A., 97, 7124-7129.
5 Zaki, ?. E. A.; Morsy, E. M.; Abdel-Motti, F. M.; Abdel-Megeid, F. ?. E. (2004), The Behaviour of Ethyl 1-acetyl-4-aryl-5-cyano-3-methyI-1,4-dihydropyrano[2,3-c]pyrazol-6-ylimidoformate Towards Nucleophiles. Heterocycl. Commun. 10, 97-102.
6 (a) Zaki, M. E. A.; Saliman, H. A.; Hiekal, O. A.; Rashad, A. E. (2006), Pyrazolopyranopyrimidines as a Class of Anti-Inflammatory Agents. Z. Naturforsch., C: Biosci. 61,1-5; (b) Mandha, S. R.; Siliveri, S.; Alla, M.; Bommena, V. R.; Bommineni, M. R.; Balasubramanian, S. (2012), Eco-friendly synthesis and biological evaluation of substituted pyrano[2,3-c]pyrazoles. Bioorg. Med. Chem. Lett. 22, 5272-5278.
7 Foloppe, N.; Fisher, L. M.; Howes, R.; Potter, A.; Robertson, A. G. S.; Surgenor, A. E. (2006), Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening. Bioorg. Med. Chem. 14, 4792-4802.
8 (a) Abdelrazek, F. M.; Metz1, P.; Kataeva1, O.; J?ger, A.; El-Mahrouky, S. F. (2007), Synthesis and Molluscicidal Activity of New Chromene and Pyrano[2,3-c]pyrazole Derivatives. Arch. Pharm. Chem. Life Sci. 340, 543-548; (b) Abdelrazek, F. M.; Michael, F. A.; Mohamed. A. E. (2006), Synthesis and Molluscicidal Activity of Some 1,3,4-Triaryl-5-chloropyrazole, Pyrano[2,3-c]pyrazole, Pyrazolylphtha lazine and Pyrano[2,3-d]thiazole Derivatives. Arch. Pharm. Chem. Life Sci. 339, 305-312.
9 Ramiz, M. M. M.; Abdel Hafiz, I. S.; Abdel Reheim, M. A. M.; Gaber, H. M. (2012), Pyrazolones as Building Blocks in Heterocyclic Synthesis: Synthesis of New Pyrazolopyran, pyrazolopyridazine and Pyrazole Derivatives of Expected Antifungicidal Activity. J. Chin. Chem. Soc. 59, 72-80.
10 Wamhoff, H.; Kroth, E.; Strauch, K. (1993), Dihalogentriphenylphosphorane in der Heterocyclensynthese; 271: Heterokondensierte 1,2,4-Triazolo[1,5-c]pyrimidine aus Enaminonitrilen via O-Ethylformimide. Synthesis 11, 1129-1132.
11 (a) Hafez, E. A. A.; Elnagdi, M. H.; Elagamey, A. G. A.; Ei-Taweel, F. M. A. A. (1987), Nitriles in Heterocyclic Synthesis: Novel Synthesis of Benzo[c]coumarin and of Benzo[c]pyrano[3,2-c]quinoline Derivatives. Heterocycles 26, 903-907; (b) Armetso, D.; Horspool, W. M.; Martin, N.; Ramos, A.; Seaone, C. (1989), Synthesis of Cyclobutenes by the Novel Photo- chemical Ring Contraction of 4-Substituted-2-amino-3,5- dicyano-6-phenyl-4H-pyrans. J. Org. Chem. 54, 3069-3072.
12 Junek, H.; Aigner, H. (1973), Synthesen mit Nitrilen, XXXV: Reaktionen von Tetracyan?thylen mit Heterocyclen. Chem. Ber. 106, 914-921.
13 Otto, H. H. (1974), Synthesis of Some 4H-Pyrano[2.3-c]pyrazoles. Arch. Pharm. 307, 444-447.
14 (a) Sharanin, Y. A.; Shcherbina, L. N.; Sharanina, L. G.; Puzanova, V. V. (1983), Nitrile cyclization reactions, VI: Synthesis of 2-amino-4-(2-furyl)-4H-pyrans. Zh. Org. Khim. 19, 164-173; (b) Shestopalov, A. M.; Yakubov, A. P.; Tsyganov, D. V.; Emel & apos; yanova, Y. M.; Nesterov, V. N. (2002), Synthesis of substituted 6-amino-4-aryl-5-cyano-2H,4H-pyrano[2,3-c]pyrazoles. Crystal and molecular structure of 6-amino-5-cyano-3-methyl-4-(2 & apos; ,4 & apos; ,6 & apos; -triethylphenyl)-2H,4H-pyrano[2,3-c]pyrazole. Chem. Heterocycl. Compd. 38, 1180-1189; (c) Jin, T.-S.; Zhao, R.-Q.; Li, T.-S. (2006), An one-pot three-component process for the synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles in aqueous media. Arkivoc xi, 176-182; (d) Jin, T.-S.; Wang, A.-Q.; Cheng, Z.-L.; Zhang, J.-S.; 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; (e) Thumar, N. J.; Patel, M. P. (2009), Synthesis and in vitro antimicrobial evaluation of 4H-pyrazolopyran, -benzopyran and naphthopyran derivatives of 1H-pyrazole. Arkivoc 13, 363-380; (f) Dawane, B. S.; Yemul, O. S.; Chobe, S. S.; Mandawad, G. G.; Kamble, R. D.; Shinde, A. V.; Kale, V. S.; Hurne, A. O.; Pawde, M. A.; Kale, M. P.; Desai, N. P.; Salgare, R. R.; Patil, M. B.; Mundhe, S. N.; Chavan, S. R. (2011), One-pot multicomponent synthesis and antimicrobial evaluation of some novel pyrano-[2,3-c]-pyrazoles derivatives. Der Pharma Chem. 3 (3), 300-305; (g) Mohamed, N. R.; Khaireldin, N. Y.; Fahmyb, A. F.; El-Sayeda, A. A. (2010), Facile synthesis of fused nitrogen containing heterocycles as anticancer agents. Der Pharma Chem. 2 (1), 400-417; (h) Prajapati, S. P.; Patel, D. P.; Patel, P. S. (2012), Synthesis, Characterization and Antimicrobial activity of 6-amino-4-(substitutedphenyl)-1-(2,4-dinitrophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile derivatives. J. Chem. Pharm. Res. 4, 2652-2655; (i) Shi, D.; Mou, J.; Zhuang, Q.; Niu, L.; Wu, N.; 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; (j) Xiang, W. S.; Wei, W.; Tai, T. L. (2005), Synthesis of 1, 4-Dihydropyrano[2,3-c]pyrazole derivatives with no catalyst under ultrasound irradiation. E-J. Chem. 2, 121-125.
15 (a) Shestopalov, A. M.; Emeliyanova, Y. M.; Shestopalov, A. A.; Rodinovskaya, L. A.; Niazimbetova, Z. I.; Evans, D. H. (2002), One-Step Synthesis of Substituted 6-Amino-5- cyanospiro-4-(piperidine-4 & apos; )-2H,4H-dihydropyrazolo[3,4-b]pyrans. Org. Lett. 4, 423-425; (b) Shestopalov, A. M.; Emeliyanova, Y. M.; Shestopalov, A. A.; Rodinovskaya, L. A.; Niazimbetova, Z. I.; Evans, D. H. (2003), Cross-condensation of derivatives of cyanoacetic acid and carbonyl compounds. Part 1: Single-stage synthesis of 1 & apos; -substituted 6-amino-spiro-4-(piperidine-4 & apos; )-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitriles. Tetrahedron 59, 7491-7496.
16 Vasuki, G.; Kandhasamy, K. (2008), Rapid four-component reactions in water: synthesis of pyranopyrazoles. Tetrahedron Lett. 49, 5636-5638.
17 Siddekha, A.; Nizam, A.; Pasha, M. A. (2011), An efficient and simple approach for the synthesis of pyranopyrazoles using imidazole (catalytic) in aqueous medium, and the vibrational spectroscopic studies on 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole using density functional theory. Spectrochim. Acta A, 81, 431-440.
18 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 (5), 81-86.
19 Gogoi, S.; Zhao, C.-G. (2009), Organocatalyzed enantioselective synthesis of 6-amino-5- cyanodihydropyrano[2,3-c]pyrazoles. Tetrahedron Lett. 50, 2252-2255.
20 Kanagaraj, K.; Pitchumani, K. (2010), Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-b-cyclodextrin as a remarkable catalyst and host. Tetrahedron Lett. 51, 3312-3316.
21 Ebrahimi, J.; Mohanndi, A.; Pakjoo, V.; Bahramzadeh, E.; 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.
22 Khurana, J. M.; Chaudhary, A. (2012), Efficient and green synthesis of 4H-pyrans and 4H-pyrano[2,3-c]pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions. Green Chem. Lett. Rev. 5, 633-638.
23 Mecadon, H.; Rohman, M. R.; Kharbangar, I.; Laloo, B. M.; Kharkongor, I.; Rajbangshi, M.; Myrboh, B. (2011), L-Proline as an efficient catalyst for the multi-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in water. Tetrahedron Lett. 52, 3228-3231.
24 Chavan, H. V.; Babar, S. B.; Hoval, R. U.; 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.
25 Reddy, M. B. M.; Jayashankara, V. P.; Pasha, M. A. (2010), Glycine-catalyzed efficient synthesis of pyranopyrazoles via one-pot multicomponent reaction. Synth. Commun. 40, 2930-2934.
26 Kathrotiya, H. G.; Patel, R. G.; Patel, M. P. (2012), Microwave-assisted multi-component synthesis of indol-3-yl substituted pyrano[2,3-c]pyrazoles and their antimicrobial activity. J. Serb. Chem. Soc.77, 983-991.
27 Wu, M.-S.; Kong, D.-L.; Zhang, X.-Z. (2011), 6-Amino-3-methyl-4-(3-nitrophenyl)-1-phenyl-1H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile. Acta Cryst. E67, o1454-o1455.
28 Reddy, M. B. M.; Pasha, M. A. (2012), One-pot, multicomponent synthesis of 4H-pyrano[2,3-c]pyrazoles in water at 25 °C. Indian J. Chem. 51B, 537-541.
29 Khurana, J. M.; Nand, B.; Kumar, S. (2011), Rapid synthesis of polyfunctionalized pyrano[2,3-c]pyrazoles via multicomponent condensation in room-temperature liquids. Synth. Commun. 41, 405-410.
30 Shinde, P. V.; Gujar, J. B.; Shingate, B. B.; 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 Babaie, M.; Sheibani, H. (2011), Nanosized magnesium oxide as a highly effective heterogeneous base catalyst for the rapid synthesis of pyranopyrazoles via a tandem four-component reaction. Arabian J. Chem. 4, 159-162.
32 Azzam, S. H. S.; 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 Lett. 53, 6834-6837.
33 Wu, M.; Feng, Q.; Wan, D.; Ma, J. (2013), CTACl as Catalyst for four-component one-pot synthesis of pyranopyrazole derivatives in aqueous medium. Synth. Commun. 43, 1721-1726.
34 Nagarajan, A. S.; Reddy, B. S. R. (2009), Synthesis of Substituted Pyranopyrazoles under Neat Conditions via a Multicomponent Reaction. Synlett 2002-2004.
35 Bihani, M.; Bora, P. P.; Bez, G. (2013), A catalytic-free synthesis of 6-Amino-4 Alkyl/Aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-carbonitrile in Aqueous Medium. J. Chem. 2013, Article ID 920719, 8 pages, doi:10.1155/2013/920719.
36 Zhou, J.-F.; Tu, S.-J.; Zhu, H.-Q.; Zhi, S.-J. (2002), A facial one-pot synthesis of pyrano[2,3-c]pyrazole derivatives under microwave irradiation. Synth. Commun. 32, 3363-3366.
37 Guo, S.-B.; Wang, S.-X.; Li, J.-T. (2007), 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, 2111-2120.
38 Pirrung, M. C. (2006), Acceleration of Organic Reactions through Aqueous Solvent Effects. Chem. Eur. J. 12, 1312-1317.
39 Chitra, S.; Paul, N.; Muthusbramanian, S.; Manisankar, P. (2011), A facile, water mediated, microwave-assisted synthesis of 4,6-diaryl-2,3,3a,4-tetrahydro-1H-pyrido[3,2,1-jk]carbazoles by a domino Fischer indole reaction–intramolecular cyclization sequence. Green Chem. 13, 2777-2785.
40 Organic Reactions in Water: Principles, Strategies and Applications, editor: Lindstr?m, U. M. Blackwell Publishing: Oxford, U. K., 2007; p. 60.
41 Comprehensive Organic Reactions in Aqueous Media, editors: Li, C.-J. Chan, T.-H., 2nd ed.; John Wiley & Sons, Hoboken, New Jersey, U. S. A. 2007, p. 2.
42 Lindstrom, U. M. (2002), Stereoselective organic reactions in Water. Chem. Rev. 102, 2751-2772.
43 Candeias, N. R., Cal, P. M. S. D., Andre, V.; Duarte, M. T.; Veiros, L. F.; Gois, P. M. P. (2010), Water as the reaction medium for multicomponent reactions based on boronic acids. Tetrahedron 66, 2736-2745.
44 Moorhoff, C. M.; Schneider, D. F. (1998), Sodium benzoate as a mild base catalyst for the tandem Michael–Aldol self-condensation of ?,B-unsaturated ?-ketoesters. Monatsh. Chem. 129, 409-417.
45 Liu, Q.; Zhang, Y.-N. (2011), One-pot synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones catalyzed by sodium benzoate in aqueous media: A green chemistry strategy. Bull. Korean Chem. Soc. 32, 3559-3560.
46 Liu, Q.; Ai, H.-M. (2012), Sodium benzoate as s green, efficient, and recyclable catalyst for Knoevenagel condensation. Synth. Commun. 42, 3004-3010.
47 D. K. Yadav, M. A. (2012), Quraishi, Electrochemical investigation of substituted pyranopyrazoles adsorption on mild steel in acid solution. Ind. Eng. Chem. Res. 51, 8194-8210.
48 Saha, M.; Pal, A. K. (2012), Palladium (0) Nanoparticles: A Novel and Reusable Catalyst for the Synthesis of Various Pyran Derivatives. Adv. Nanopart. 1, 61-70.
2 Kuo, S. C.; Huang, L. J.; Nakamura, H. (1984), Studies on heterocyclic compounds. 6. Synthesis and analgesic and antiinflammatory activities of 3,4-dimethyl-pyra- 2,3-c]pyrazol-6-one derivatives. J. Med. Chem. 27, 539-544.
3 Ahluwalia, V. K.; Dahiya, A.; Garg, V. (1997), Reaction of 5-amino-4-formyl-3-methyl(or phenyl)-1-phenyl-1H-pyrazoles with active methylene compounds: Synthesis of fused heterocyclic rings. Indian J. Chem. 36B, 88-90.
4 Wang, J. L.; Liu, D.; Zheng, Z. J.; Shan, S.; Han, X.; Srinivasula, S. M.; Croce, C. M.; Alnemri, E. S.; Huang, Z. (2009), Structure-based discovery of an organic compound that bind Bc1-2 protein and induces apoptosis of tumor cells. Proc. Natl. Acad. Sci. U.S.A., 97, 7124-7129.
5 Zaki, ?. E. A.; Morsy, E. M.; Abdel-Motti, F. M.; Abdel-Megeid, F. ?. E. (2004), The Behaviour of Ethyl 1-acetyl-4-aryl-5-cyano-3-methyI-1,4-dihydropyrano[2,3-c]pyrazol-6-ylimidoformate Towards Nucleophiles. Heterocycl. Commun. 10, 97-102.
6 (a) Zaki, M. E. A.; Saliman, H. A.; Hiekal, O. A.; Rashad, A. E. (2006), Pyrazolopyranopyrimidines as a Class of Anti-Inflammatory Agents. Z. Naturforsch., C: Biosci. 61,1-5; (b) Mandha, S. R.; Siliveri, S.; Alla, M.; Bommena, V. R.; Bommineni, M. R.; Balasubramanian, S. (2012), Eco-friendly synthesis and biological evaluation of substituted pyrano[2,3-c]pyrazoles. Bioorg. Med. Chem. Lett. 22, 5272-5278.
7 Foloppe, N.; Fisher, L. M.; Howes, R.; Potter, A.; Robertson, A. G. S.; Surgenor, A. E. (2006), Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening. Bioorg. Med. Chem. 14, 4792-4802.
8 (a) Abdelrazek, F. M.; Metz1, P.; Kataeva1, O.; J?ger, A.; El-Mahrouky, S. F. (2007), Synthesis and Molluscicidal Activity of New Chromene and Pyrano[2,3-c]pyrazole Derivatives. Arch. Pharm. Chem. Life Sci. 340, 543-548; (b) Abdelrazek, F. M.; Michael, F. A.; Mohamed. A. E. (2006), Synthesis and Molluscicidal Activity of Some 1,3,4-Triaryl-5-chloropyrazole, Pyrano[2,3-c]pyrazole, Pyrazolylphtha lazine and Pyrano[2,3-d]thiazole Derivatives. Arch. Pharm. Chem. Life Sci. 339, 305-312.
9 Ramiz, M. M. M.; Abdel Hafiz, I. S.; Abdel Reheim, M. A. M.; Gaber, H. M. (2012), Pyrazolones as Building Blocks in Heterocyclic Synthesis: Synthesis of New Pyrazolopyran, pyrazolopyridazine and Pyrazole Derivatives of Expected Antifungicidal Activity. J. Chin. Chem. Soc. 59, 72-80.
10 Wamhoff, H.; Kroth, E.; Strauch, K. (1993), Dihalogentriphenylphosphorane in der Heterocyclensynthese; 271: Heterokondensierte 1,2,4-Triazolo[1,5-c]pyrimidine aus Enaminonitrilen via O-Ethylformimide. Synthesis 11, 1129-1132.
11 (a) Hafez, E. A. A.; Elnagdi, M. H.; Elagamey, A. G. A.; Ei-Taweel, F. M. A. A. (1987), Nitriles in Heterocyclic Synthesis: Novel Synthesis of Benzo[c]coumarin and of Benzo[c]pyrano[3,2-c]quinoline Derivatives. Heterocycles 26, 903-907; (b) Armetso, D.; Horspool, W. M.; Martin, N.; Ramos, A.; Seaone, C. (1989), Synthesis of Cyclobutenes by the Novel Photo- chemical Ring Contraction of 4-Substituted-2-amino-3,5- dicyano-6-phenyl-4H-pyrans. J. Org. Chem. 54, 3069-3072.
12 Junek, H.; Aigner, H. (1973), Synthesen mit Nitrilen, XXXV: Reaktionen von Tetracyan?thylen mit Heterocyclen. Chem. Ber. 106, 914-921.
13 Otto, H. H. (1974), Synthesis of Some 4H-Pyrano[2.3-c]pyrazoles. Arch. Pharm. 307, 444-447.
14 (a) Sharanin, Y. A.; Shcherbina, L. N.; Sharanina, L. G.; Puzanova, V. V. (1983), Nitrile cyclization reactions, VI: Synthesis of 2-amino-4-(2-furyl)-4H-pyrans. Zh. Org. Khim. 19, 164-173; (b) Shestopalov, A. M.; Yakubov, A. P.; Tsyganov, D. V.; Emel & apos; yanova, Y. M.; Nesterov, V. N. (2002), Synthesis of substituted 6-amino-4-aryl-5-cyano-2H,4H-pyrano[2,3-c]pyrazoles. Crystal and molecular structure of 6-amino-5-cyano-3-methyl-4-(2 & apos; ,4 & apos; ,6 & apos; -triethylphenyl)-2H,4H-pyrano[2,3-c]pyrazole. Chem. Heterocycl. Compd. 38, 1180-1189; (c) Jin, T.-S.; Zhao, R.-Q.; Li, T.-S. (2006), An one-pot three-component process for the synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles in aqueous media. Arkivoc xi, 176-182; (d) Jin, T.-S.; Wang, A.-Q.; Cheng, Z.-L.; Zhang, J.-S.; 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; (e) Thumar, N. J.; Patel, M. P. (2009), Synthesis and in vitro antimicrobial evaluation of 4H-pyrazolopyran, -benzopyran and naphthopyran derivatives of 1H-pyrazole. Arkivoc 13, 363-380; (f) Dawane, B. S.; Yemul, O. S.; Chobe, S. S.; Mandawad, G. G.; Kamble, R. D.; Shinde, A. V.; Kale, V. S.; Hurne, A. O.; Pawde, M. A.; Kale, M. P.; Desai, N. P.; Salgare, R. R.; Patil, M. B.; Mundhe, S. N.; Chavan, S. R. (2011), One-pot multicomponent synthesis and antimicrobial evaluation of some novel pyrano-[2,3-c]-pyrazoles derivatives. Der Pharma Chem. 3 (3), 300-305; (g) Mohamed, N. R.; Khaireldin, N. Y.; Fahmyb, A. F.; El-Sayeda, A. A. (2010), Facile synthesis of fused nitrogen containing heterocycles as anticancer agents. Der Pharma Chem. 2 (1), 400-417; (h) Prajapati, S. P.; Patel, D. P.; Patel, P. S. (2012), Synthesis, Characterization and Antimicrobial activity of 6-amino-4-(substitutedphenyl)-1-(2,4-dinitrophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile derivatives. J. Chem. Pharm. Res. 4, 2652-2655; (i) Shi, D.; Mou, J.; Zhuang, Q.; Niu, L.; Wu, N.; 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; (j) Xiang, W. S.; Wei, W.; Tai, T. L. (2005), Synthesis of 1, 4-Dihydropyrano[2,3-c]pyrazole derivatives with no catalyst under ultrasound irradiation. E-J. Chem. 2, 121-125.
15 (a) Shestopalov, A. M.; Emeliyanova, Y. M.; Shestopalov, A. A.; Rodinovskaya, L. A.; Niazimbetova, Z. I.; Evans, D. H. (2002), One-Step Synthesis of Substituted 6-Amino-5- cyanospiro-4-(piperidine-4 & apos; )-2H,4H-dihydropyrazolo[3,4-b]pyrans. Org. Lett. 4, 423-425; (b) Shestopalov, A. M.; Emeliyanova, Y. M.; Shestopalov, A. A.; Rodinovskaya, L. A.; Niazimbetova, Z. I.; Evans, D. H. (2003), Cross-condensation of derivatives of cyanoacetic acid and carbonyl compounds. Part 1: Single-stage synthesis of 1 & apos; -substituted 6-amino-spiro-4-(piperidine-4 & apos; )-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitriles. Tetrahedron 59, 7491-7496.
16 Vasuki, G.; Kandhasamy, K. (2008), Rapid four-component reactions in water: synthesis of pyranopyrazoles. Tetrahedron Lett. 49, 5636-5638.
17 Siddekha, A.; Nizam, A.; Pasha, M. A. (2011), An efficient and simple approach for the synthesis of pyranopyrazoles using imidazole (catalytic) in aqueous medium, and the vibrational spectroscopic studies on 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole using density functional theory. Spectrochim. Acta A, 81, 431-440.
18 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 (5), 81-86.
19 Gogoi, S.; Zhao, C.-G. (2009), Organocatalyzed enantioselective synthesis of 6-amino-5- cyanodihydropyrano[2,3-c]pyrazoles. Tetrahedron Lett. 50, 2252-2255.
20 Kanagaraj, K.; Pitchumani, K. (2010), Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-b-cyclodextrin as a remarkable catalyst and host. Tetrahedron Lett. 51, 3312-3316.
21 Ebrahimi, J.; Mohanndi, A.; Pakjoo, V.; Bahramzadeh, E.; 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.
22 Khurana, J. M.; Chaudhary, A. (2012), Efficient and green synthesis of 4H-pyrans and 4H-pyrano[2,3-c]pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions. Green Chem. Lett. Rev. 5, 633-638.
23 Mecadon, H.; Rohman, M. R.; Kharbangar, I.; Laloo, B. M.; Kharkongor, I.; Rajbangshi, M.; Myrboh, B. (2011), L-Proline as an efficient catalyst for the multi-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in water. Tetrahedron Lett. 52, 3228-3231.
24 Chavan, H. V.; Babar, S. B.; Hoval, R. U.; 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.
25 Reddy, M. B. M.; Jayashankara, V. P.; Pasha, M. A. (2010), Glycine-catalyzed efficient synthesis of pyranopyrazoles via one-pot multicomponent reaction. Synth. Commun. 40, 2930-2934.
26 Kathrotiya, H. G.; Patel, R. G.; Patel, M. P. (2012), Microwave-assisted multi-component synthesis of indol-3-yl substituted pyrano[2,3-c]pyrazoles and their antimicrobial activity. J. Serb. Chem. Soc.77, 983-991.
27 Wu, M.-S.; Kong, D.-L.; Zhang, X.-Z. (2011), 6-Amino-3-methyl-4-(3-nitrophenyl)-1-phenyl-1H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile. Acta Cryst. E67, o1454-o1455.
28 Reddy, M. B. M.; Pasha, M. A. (2012), One-pot, multicomponent synthesis of 4H-pyrano[2,3-c]pyrazoles in water at 25 °C. Indian J. Chem. 51B, 537-541.
29 Khurana, J. M.; Nand, B.; Kumar, S. (2011), Rapid synthesis of polyfunctionalized pyrano[2,3-c]pyrazoles via multicomponent condensation in room-temperature liquids. Synth. Commun. 41, 405-410.
30 Shinde, P. V.; Gujar, J. B.; Shingate, B. B.; 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 Babaie, M.; Sheibani, H. (2011), Nanosized magnesium oxide as a highly effective heterogeneous base catalyst for the rapid synthesis of pyranopyrazoles via a tandem four-component reaction. Arabian J. Chem. 4, 159-162.
32 Azzam, S. H. S.; 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 Lett. 53, 6834-6837.
33 Wu, M.; Feng, Q.; Wan, D.; Ma, J. (2013), CTACl as Catalyst for four-component one-pot synthesis of pyranopyrazole derivatives in aqueous medium. Synth. Commun. 43, 1721-1726.
34 Nagarajan, A. S.; Reddy, B. S. R. (2009), Synthesis of Substituted Pyranopyrazoles under Neat Conditions via a Multicomponent Reaction. Synlett 2002-2004.
35 Bihani, M.; Bora, P. P.; Bez, G. (2013), A catalytic-free synthesis of 6-Amino-4 Alkyl/Aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-carbonitrile in Aqueous Medium. J. Chem. 2013, Article ID 920719, 8 pages, doi:10.1155/2013/920719.
36 Zhou, J.-F.; Tu, S.-J.; Zhu, H.-Q.; Zhi, S.-J. (2002), A facial one-pot synthesis of pyrano[2,3-c]pyrazole derivatives under microwave irradiation. Synth. Commun. 32, 3363-3366.
37 Guo, S.-B.; Wang, S.-X.; Li, J.-T. (2007), 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, 2111-2120.
38 Pirrung, M. C. (2006), Acceleration of Organic Reactions through Aqueous Solvent Effects. Chem. Eur. J. 12, 1312-1317.
39 Chitra, S.; Paul, N.; Muthusbramanian, S.; Manisankar, P. (2011), A facile, water mediated, microwave-assisted synthesis of 4,6-diaryl-2,3,3a,4-tetrahydro-1H-pyrido[3,2,1-jk]carbazoles by a domino Fischer indole reaction–intramolecular cyclization sequence. Green Chem. 13, 2777-2785.
40 Organic Reactions in Water: Principles, Strategies and Applications, editor: Lindstr?m, U. M. Blackwell Publishing: Oxford, U. K., 2007; p. 60.
41 Comprehensive Organic Reactions in Aqueous Media, editors: Li, C.-J. Chan, T.-H., 2nd ed.; John Wiley & Sons, Hoboken, New Jersey, U. S. A. 2007, p. 2.
42 Lindstrom, U. M. (2002), Stereoselective organic reactions in Water. Chem. Rev. 102, 2751-2772.
43 Candeias, N. R., Cal, P. M. S. D., Andre, V.; Duarte, M. T.; Veiros, L. F.; Gois, P. M. P. (2010), Water as the reaction medium for multicomponent reactions based on boronic acids. Tetrahedron 66, 2736-2745.
44 Moorhoff, C. M.; Schneider, D. F. (1998), Sodium benzoate as a mild base catalyst for the tandem Michael–Aldol self-condensation of ?,B-unsaturated ?-ketoesters. Monatsh. Chem. 129, 409-417.
45 Liu, Q.; Zhang, Y.-N. (2011), One-pot synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones catalyzed by sodium benzoate in aqueous media: A green chemistry strategy. Bull. Korean Chem. Soc. 32, 3559-3560.
46 Liu, Q.; Ai, H.-M. (2012), Sodium benzoate as s green, efficient, and recyclable catalyst for Knoevenagel condensation. Synth. Commun. 42, 3004-3010.
47 D. K. Yadav, M. A. (2012), Quraishi, Electrochemical investigation of substituted pyranopyrazoles adsorption on mild steel in acid solution. Ind. Eng. Chem. Res. 51, 8194-8210.
48 Saha, M.; Pal, A. K. (2012), Palladium (0) Nanoparticles: A Novel and Reusable Catalyst for the Synthesis of Various Pyran Derivatives. Adv. Nanopart. 1, 61-70.