Abstract
An efficient and simple method for the synthesis of aliphatic and aromatic 1H-indazolo[2,1-b]phthalazinetrione derivatives through a one-pot three-component condensation of phthalhydrazide, aldehyde, and dimedone in the presence of boron sulfonic acid as a reusable and efficient catalyst under solvent-free conditions is described. The reusability of catalyst, good to excellent yields, short reaction times, and the avoidance of harsh reagents are the main advantages of this method.
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Zhu J, Bienaymé H (2005) Multicomponent reactions. Wiley-VCH, Weinheim
Dömling A (2006) Chem Rev 106:17
Dömling A, Ugi I (2000) Angew Chem Int Ed 39:3169
Ramón DJ, Yus M (2005) Angew Chem Int Ed 44:1602
Ma C, Yang Y (2005) Org Lett 7:1343
Cheng Y, Meth-Cohn O (2004) Chem Rev 104:2507
Ruijter E, Scheffelaar R, Orru RVA (2011) Angew Chem Int Ed 50:6234
Franklin EC (1935) Chem Rev 16:305
Bergstrom FW (1944) Chem Rev 35:77
Lichtenthaler FW (2002) Acc Chem Res 35:728
Litvinov VP (2003) Russ Chem Rev 72:69
Al-Assar F, Zelenin KN, Lesiovskaya EE, Bezhan IP, Chahchir BA (2002) Pharm Chem J 36:598
Jain RP, Vederas JC (2004) Bioorg Med Chem Lett 14:3655
Carling RW, Moore KW, Street LJ, Wild D, Isted C, Lesson PD, Thomas S, O’Cooner D, Mckernan RM, Quirk K, Cook SM, Atach JR, Waftord KA, Thompson SA, Dawson GR, Ferris P, Castro JL (2004) J Med Chem 47:1807
Watanabe N, Kabasawa Y, Takase Y, Matsukura M, Miyazaki K, Ishihara H, Kodama K, Adachi H (1998) J Med Chem 41:3367
Nomoto Y, Obase H, Takai H, Teranishi M, Nakamura J, Kubo K (1990) Chem Pharm Bull 38:2179
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 Des 73:313
Sinkkonen J, Ovcharenko V, Zelenin KN, Bezhan IP, Chakchir BA, Al-Assar F, Pihlaja K (2002) Eur J Org Chem 2002:2046
Ryu CK, Park RE, Ma MY, Nho JH (2007) Bioorg Med Chem Lett 17:2577
Li J, Zhao YF, Yuan XY, Xu JX, Gong P (2006) Molecules 11:574
Sayyafi M, Seyyedhamzeh M, Khavasi HR, Bazgir A (2008) Tetrahedron 64:2375
Shaterian HR, Ghashang M, Feyzi M (2008) Appl Catal A 345:128
Khurana JM, Magoo D (2009) Tetrahedron Lett 50:7300
Shaterian HR, Hosseinian A, Ghashang M (2009) Arkivoc 59
Shaterian HR, Khorami F, Amirzadeh A, Doostmohammadi R, Ghashang M (2009) J Iran Chem Res 2:57
Wang HJ, Zhang XN, Zhang ZH (2010) Monatsh Chem 141:425
Ghorbani-Vaghei R, Karimi-Nami R, Toghraei-Semiromi Z, Amiri M, Ghavidel M (2011) Tetrahedron 67:1930
Hasaninejad A, Zare A, Shekouhy M (2011) Tetrahedron 67:390
Wang X, Ma W, Wu L, Yan FL (2010) J Chin Chem Soc 57:1341
Hamidian H, Fozooni S, Hassankhani A, Mohammadi SZ (2011) Molecules 16:9041
Kiasat AR, Mouradzadegun A, Saghanezhad SJ (2013) J Serb Chem Soc 78:469
Salehi P, Zolfigol MA, Shirini F, Baghbanzadeh M (2006) Curr Org Chem 10:2171
Salehi P, Zolfigol MA, Fard MA (2004) J Braz Chem Soc 15:773
Kiasat AR, Fallah-Mehrjardi M (2008) J Braz Chem Soc 19:1595
Sajjadifar S, Mirshokraie SA, Javaherneshan N, Louie O (2012) Am J Org Chem 2:1
Sajjadifar S (2013) Int J ChemTech Res 5:385
Sajjadifar S, Khosravani E, Shiri S (2013) Int J ChemTech Res 5:1969
Sajjadifar S, Rezayati S (2013) Int J ChemTech Res 5:1964
Zolfigol MA, Khazaei A, Vahedi H, Mokhlesi M, Sajadifar S, Pirveysian M (2012) Phosphorus Sulfur Silicon Relat Elem 187:295
Zolfigol MA, Vahedi H, Massoudi AH, Sajjadifar S, Loui O, Javaherneshan N (2011) Clin Biochem 44:219
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The authors gratefully acknowledge the Payame Noor University (PNU) of Ilam for partial support of this work.
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Soheilizad, M., Adib, M. & Sajjadifar, S. One-pot and solvent-free synthesis of aliphatic and aromatic 1H-indazolo[2,1-b]phthalazinetriones catalyzed by boron sulfonic acid. Monatsh Chem 145, 1353–1356 (2014). https://doi.org/10.1007/s00706-014-1194-9
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DOI: https://doi.org/10.1007/s00706-014-1194-9