Abstract
Efficient one-pot condensation of aldehyde, dimedone, and phthalhydrazide has been achieved in the presence of a catalytic amount of tungstosilicic acid under solvent-free conditions. A variety of 1H-indazolo[1,2-b]phthalazinetrione derivatives were prepared in high to excellent yields in short time.
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References
Khalil AM, Berghot MA, Gouda MA (2009) Eur J Med Chem 44:4448
Kim JS, Lee H-J, Suh M-E, Choo H-YP, Lee SK, Park HJ, Kim C, Park SW, Lee C-O (2004) Bioorg Med Chem 12:3683
Kim JS, Rhee H-K, Park HJ, Lee SK, Lee C-O, Park Choo H-Y (2008) Bioorg Med Chem 16:4545
El-Sakka SS, Soliman AH, Imam AM (2009) Afinidad 66:167
Zhang L, Guan LP, Sun XY, Wei CX, Chai KY, Quan ZS (2009) Chem Bio Drug Design 73:313
Ryu C-K, Park R-E, Ma M-Y, Nho J-H (2007) Bioorg Med Chem Lett 17:2577
Li J, Zhao YF, Yuan XY, Xu JX, Gong P (2006) Molecules 11:574
Sinkkonen J, Ovcharenko V, Zelenin KN, Bezhan IP, Chakchir BA, Al-Assar F, Pihlaja K (2002) Eur J Org Chem 2046
Sung Kim J, Lee H-J, Suh M-E, Choo H-YP, Lee SK, Park HJ, Kim C, Park SW, Lee C-O (2009) Bioorg Med Chem 17:731
Piatnitski EL, Duncton MAJ, Kiselyov AS, Katoch-Rouse R, Sherman D, Milligan DL, Balagtas C, Wong WC, Kawakami J, Doody JF (2005) Bioorg Med Chem Lett 15:4696
Duncton MAJ, Piatnitski EL, Katoch-Rouse R, Smith LM, Kiselyov AS, Milligan DL, Balagtas C, Wong WC, Kawakami J, Doody JF (2006) Bioorg Med Chem Lett 16:1579
Wu H, Chen XM, Wan Y, Xin HQ, Xu HH, Ma R, Yue CH, Pang LL (2009) Lett Org Chem 6:219
Ghahremanzadeh R, Shakibaei GI, Bazgir A (2008) Synlett 1129
Nabid MR, Rezaei SJT, Ghahremanzadeh R, Bazgir A (2010) Ultrason Sonochem 17:159
Ghahremanzadeh R, Ahadi S, Sayyafi M, Bazgir A (2008) Tetrahedron Lett 49:4479
Liu L-P, Lu J-M, Shi M (2007) Org Lett 9:1303
Ueda T, Kotsuki H (2008) Heterocycles 76:73
Martins MAP, Frizzo CP, Moreira DN, Buriol L, Machado P (2009) Chem Rev 109:4140
Liu Y-H, Liu Q-S, Zhang Z-H (2009) Tetrahedron Lett 50:916
Liu Y-H, Zhang Z-H, Li T-S (2008) Synthesis 3314
Liu Y-H, Liu Q-S, Zhang Z-H (2008) J Mol Catal A Chem 296:42
Zhang P, Zhang Z-H (2009) Monatsh Chem 140:199
Zhang Z-H, Wang H-J, Liu X-Q, Zhang Y-Y (2009) Monatsh Chem 140:1481
Wang H-J, Liu X-Q, Zhang Y-Y, Zhang Z-H (2009) J Braz Chem Soc 20:1939
Wang G-W, Shen Y-B, Wu X-L, Wang L (2008) Tetrahedron Lett 49:5090
Wang G-W, Shen Y-B, Wu X-L (2008) Eur J Org Chem 4367
Yang L, Xu L-W, Xia C-G (2008) Tetrahedron Lett 49:2882
Kozhevnikov IV (2009) J Mol Catal A Chem 305:104
Chaskar A, Padalkar V, Phatangare K, Patil K, Bodkhe A, Langi B (2009) Appl Catal A Gen 359:84
Celik FE, Lawrence H, Bell AT (2008) J Mol Catal A Chem 288:87
Sayyafi M, Seyyedhamzeh M, Khavasi HR, Bazgir A (2008) Tetrahedron 64:2375
Shaterian HR, Ghashang M, Feyzi M (2008) Appl Catal A Gen 345:128
Khurana JM, Magoo D (2009) Tetrahedron Lett 50:7300
Shaterian HR, Hosseinian A, Ghashang M (2009) Arkivoc ii:59
Shaterian HR, Khorami F, Amirzadeh A, Doostmohammadi R, Ghashang M (2009) J Iran Chem Res 2:57
Lipson VV, Desenko SM, Borodina VV, Shirobokova MG, Musatov VI (2005) Russ J Org Chem 41:115
Das B, Krishnaish M, Laxminarayana K, Damodar K, Kumar DN (2008) Chem Lett 37:1000
Acknowledgments
We thank the National Natural Science Foundation of China (20872025), the Nature Science Foundation of Hebei Province (B2008000149), and the Research Foundation for the Graduate Program of Hebei Normal University for financial support.
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Wang, HJ., Zhang, XN. & Zhang, ZH. Highly efficient three-component synthesis of 1H-indazolo[1,2-b]phthalazinetrione derivatives catalyzed by heteropolyacids. Monatsh Chem 141, 425–430 (2010). https://doi.org/10.1007/s00706-010-0283-7
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DOI: https://doi.org/10.1007/s00706-010-0283-7
Keywords
- Multicomponent reaction
- 1H-indazolo[1,2-b]phthalazinetrione
- Aldehyde
- Phthalhydrazide
- Heteropolyacid
- Solvent-free conditions