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A highly flexible green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with CuI nanoparticles as catalyst under solvent-free conditions |
Javad Safaei-Ghomi, Hossein Shahbazi-Alavi, Abolfazl Ziarati, Raheleh Teymuri, Mohammad Reza Saberi |
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan 51167, Iran |
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Abstract CuI nanoparticles as an efficient catalyst have been used for the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by the four-component condensation reaction of phthalic anhydride, hydrazine monohydrate, aromatic aldehydes and malononitrile or ethyl cyanoacetate under solventfree conditions in good to excellent yields, short reaction times and environmentally benign, milder reaction conditions.
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Received: 13 August 2013
Published: 28 November 2013
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Fund: The authors are grateful to University of Kashan for supporting this work (No. 159196/XⅡV). |
Corresponding Authors:
Javad Safaei-Ghomi
E-mail: safaei@kashanu.ac.ir
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|
[25] |
I. Ugi, A. Dömling, W. Hörl, Multicomponent reactions in organic chemistry, Endeavour 18 (1994) 115-122.
|
[7] |
O. Prakash, R. Kumar, V. Parkash, Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3-aryl-4-pyrazolyl)chromones, Eur. J. Med. Chem. 43 (2008) 435-440.
|
[8] |
M.A.F. Vera-DiVaio, A.C.C. Freitas, H.C.A. Castro, et al., Synthesis, antichagasic in vitor evaluation, cytotoxicity assays, molecular modeling and SAR/QSAR studies of a 2-phenyl-3-(1-phenyl-1H-pyrazol-4-yl) acrylic acid benzylidene-carbohydrazide series, Bioorg. Med. Chem. 17 (2009) 295-302.
|
[37] |
R. Ghahremanzadeh, G. Imani Shakibaei, A. Bazgir, An efficient one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dionederivatives,Synlett8 (2008)1129-1132.
|
[28] |
D.J. Ramon, M. Yus, Asymmetric multicomponent reactions (AMCRs): the new frontier, Angew. Chem. Int. Ed. 44 (2005) 1602-1634.
|
[31] |
M. Kidwai, N.K. Mishra, V. Bansal, A. Kuma, S. Mozumdar, Novel one-pot Cunanoparticles-catalyzed Mannich reaction, Tetrahedron Lett. 50 (2009) 1355-1358.
|
[29] |
L. Lu, M.L. Sui, K. Lu, Superplastic extensibility of nanocrystalline copper at room temperature, Science 287 (2000) 1463-1466.
|
[18] |
J. Li, Y.F. Zhao, X.Y. Yuan, J.X. Xu, P. Gong, Synthesis and anticancer activities of novel 1,4-disubstituted phthalazines, Molecules 11 (2006) 574-582.
|
[2] |
H.W. Heine, R. Henrie, L. Heitz, S.R. Kovvali, Diaziridines Ⅲ. Reactions of some 1-alkyl-and 1,1-dialkyl-1H-diazirino[1,2-b]phthalazine-3,8-diones, J. Org. Chem. 39 (1974) 3187-3191.
|
[42] |
S.H. Song, J. Zhong, Y.H. He, Z. Guan, One-pot four-component synthesis of 1Hpyrazolo[1,2-b]phthalazine-5,10-dione derivatives, Tetrahedron Lett. 53 (2012) 7075-7077.
|
[16] |
L. Zhang, L.P. Guan, X.Y. Sun, et al., Synthesis and anticonvulsant activity of 6-alkoxy-[1,2,4]triazolo[3,4-a]phthalazines, Chem. Biol. Drug Des. 73 (2009) 313-319.
|
[1] |
W.R. Vaughan, The chemistry of the phthalazines, Chem. Rev. 43 (1948) 447-508.
|
[3] |
S. Rostamizadeh, M. Nojavan, R. Aryan, H. Sadeghian, M. Davoodnejad, A novel and efficient synthesis of pyrazolo[3,4-d]pyrimidine derivatives and the study of their anti-bacterial activity, Chin. Chem. Lett. 24 (2013) 629-632.
|
[4] |
N.K. Terrett, A.S. Bell, D. Brown, P. Ellis, Sildenafil (VIAGRATM), a potent and selective inhibitor of type 5cGMP, phosphodiesterase with utility for the treatment of maleerectile dysfunction, Bioorg. Med. Chem. Lett. 6 (1996) 1819-1824.
|
[5] |
S.K. Singh, P.G. Reddy, K.S. Rao, et al., Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors, Bioorg. Med. Chem. Lett. 14 (2004) 499-504.
|
[6] |
T. Nakamura, M. Sato, H. Kakinuma, et al., Pyrazole and isoxazole derivatives as new, potent, and selective 20-hydroxy-5,8,11,14-eicosatetraenoic acid synthase inhibitors, J. Med. Chem. 46 (2003) 5416-5427.
|
[12] |
P.C. Lü, J. Sun, Y. Luo, Y. Yang, H.L. Zhu, Design, synthesis, and structure activity relationships of pyrazole derivatives as potential FabH inhibitors, Bioorg. Med. Chem. Lett. 20 (2010) 4657-4660.
|
[14] |
K. Dugi, M. Mark, F. Himmelsbach, Pharmaceutical composition comprising a pyrazole-O-glucoside derivative, WO 2009022009 A 1.
|
[15] |
S.S. El-Saka, A.H. Soliman, A.M. Imam, Synthesis, antimicrobial activity and electron impact of mass spectra of phthalazine-1,4-dione derivatives, Afinidad 66 (2009) 167-172.
|
[19] |
Y. Nomoto, H. Obase, H. Takai, et al., Studies on cardiotonic agents. Ⅱ. Synthesis of novel phthalazine and 1,2,3-benzotriazine derivatives, Chem. Pharm. Bull. (Tokyo) 38 (1990) 2179-2183.
|
[20] |
N. Watanabe, Y. Kabasawa, Y. Takase, et al., 4-Benzylamino-1-chloro-6-substituted phthalazines: synthesis and inhibitory activity toward phosphodiesterase 5, J. Med. Chem. 41 (1998) 3367-3372.
|
[22] |
J. Sinkkonen, V. Ovcharenko, K.N. Zelenin, et al., 1H and 13C NMR study of 1-hydrazino-2,3-dihydro-1H-pyrazolo[1,2-a]pyridazine-5,8-diones and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and their ring-chain tautomerism, Eur. J. Org. Chem. 13 (2002) 2046-2053.
|
[24] |
A. Kumar, M.K. Gupta, M. Kumar, L-Proline catalysed multicomponent synthesis of 3-amino alkylated indoles via a Mannich-type reaction under solvent-free conditions, Green Chem. 14 (2012) 290-295.
|
[26] |
M.M. Heravi, B. Baghernejad, H.A. Oskooie, A novel three-component reaction for the synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amines, Tetrahedron Lett. 50 (2009) 767-769.
|
[33] |
A.K. Edward, L.M. Anton, S.K. Yulia, et al., Copper nanoparticles as active catalysts in hydroxylation of phenol by hydrogen peroxide, Appl. Catal. A: Gen. 385 (2010) 62-72.
|
[34] |
J. Safaei-Ghomi, A. Ziarati, R. Teymuri, CuI nanoparticles as new, efficient and reusable catalyst for the one-pot synthesis of 1,4-dihydropyridines, Bull. Korean Chem. Soc. 33 (2012) 2679-2682.
|
[36] |
A. Ziarati, J. Safaei-Ghomi, S. Rohani, Pseudo five-component process for the synthesis of functionalized tricarboxamides using CuI nanoparticles as reusable catalyst, Chin. Chem. Lett. 24 (2013) 195-198.
|
[38] |
M.R. Nabid, S.J. Tabatabaei Rezaei, R. Ghahremanzadeh, A. Bazgir, Ultrasoundassisted one-pot, three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones, Ultrason. Sonochem. 17 (2010) 159-161.
|
[39] |
D.S. Raghuvanshi, K.N. Singh, A highly efficient green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives and their photophysical studies, Tetrahedron Lett. 52 (2011) 5702-5705.
|
[41] |
G. Karthikeyan, A. Pandurangan, Post synthesis alumination of KIT-6 materials with la3d symmetry and their catalytic efficiency towards multicomponent synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione carbonitriles and carboxylates, J. Mol. Catal. A: Chem. 361-362 (2012) 58-67.
|
[9] |
M.J. Genin, C. Biles, B.J. Keiser, et al., Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3-and 4-substituted derivatives, J. Med. Chem. 43 (2000) 1034-1040.
|
[10] |
F. Wei, B.X. Zhao, B. Huang, et al., Design, synthesis, and preliminary biological evaluation of novel ethyl 1-(2'-hydroxy-3'-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate, Bioorg, Med. Chem. Lett. 16 (2006) 6342-6347.
|
[11] |
Y. Xia, Z.W. Dong, B.X. Zhao, et al., Synthesis and structure-activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives as potential agents against A549 lung cancer cells, Bioorg. Med. Chem. 15 (2007) 6893-6899.
|
[13] |
N. Cho, M. Kamaura, T. Yogo, H. Imoto, Preparation of pyrazole derivatives as improvement of insulin resistance, WO 2009139340.
|
[17] |
C.K. Ryu, R.E. Park, M.Y. Ma, J.H. Nho, Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones, Bioorg. Med. Chem. Lett. 17 (2007) 2577-2580.
|
[21] |
F. Al'-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan, B.A. Chakchir, Synthesis and pharmacological activity of 1-hydroxy, 1-amino-, and 1-hydrazino-substituted 2,3-dihydro-1H-pyrazolo[1,2-a]pyridazine-5,8-diones and 2,3-dihydro-1H-pyrazolo[1,2-b]phthalazine-5,10-diones, J. Pharm. Chem. 36 (2002) 598-603.
|
[23] |
R.P. Jain, J.C. Vederas, Structural variations in keto-glutamines for improved inhibition against hepatitis A virus 3C proteinase, Bioorg. Med. Chem. Lett. 14 (2004) 3655-3658.
|
[27] |
J. Gerencser, G. Dormon, F. Darvas, Meldrum's acid in multicomponent reaction: applications to combinatorial and diversity-oriented synthesis, QSAR Comb. Sci. 25 (2006) 439-448.
|
[30] |
Y.J. Song, C. Yoo, J.T. Hong, et al., Nanocrystalline copper oxide(Ⅱ)-catalyzed alkyne-azide cycloadditions, Bull. Korean Chem. Soc. 29 (2008) 1561-1564.
|
[32] |
A.K. Verma, R. Kumar, P. Chaudhary, et al., Cu-nanoparticles: a chemoselective catalyst for the aza-Michael reactions of N-alkyl and N-arylpiperazines with acrylonitrile, Tetrahedron Lett. 46 (2005) 5229-5232.
|
[35] |
J. Safaei-Ghomi, M.A. Ghasemzadeh, CuI nanoparticles: a highly active and easily recyclable catalyst for the synthesis of 2-amino-3,5-dicyano-6-sulfanyl pyridines, J. Sulfur Chem. 34 (2013) 233-241.
|
[40] |
H.R. Shaterian, M. Mohammadnia, Mild basic ionic liquids catalyzed new fourcomponent synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones, J. Mol. Liq. 173 (2012) 55-61.
|
[43] |
M. Veeranarayana Reddy, Y. Tae Jeeong, InCl3-catalyzed green synthesis of 1Hpyrazolo[1,2-b]phthalazine-5,10-diones under solvent-free conditions, Tetrahedron Lett. 54 (2013) 3546-3549.
|
[44] |
Y. Jiang, S.Y. Gao, Z.D. Li, X.X. Jia, Y.L. Chen, Cauliflower-like CuI nanostructures: green synthesis and applications as catalyst and adsorbent, Mater. Sci. Eng. B 176 (2011) 1021-1027.
|
[45] |
A. Azarifar, R. Nejat-Yami, D. Azarifar, Nano-ZnO: an efficient and reusable catalyst for one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and pyrazolo[1,2-a][1,2,4]triazole-1,3-diones, J. Iran. Chem. Soc. 10 (2013) 297-306.
|
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