Melamine trisulfonic acid (MTSA) as an efficient catalyst for the synthesis of triazolo[1,2-a]indazole-triones and some 2H-indazolo[2,1-b]phthalazine-triones
الموضوعات : Iranian Journal of Catalysis
Ardeshir Khazaei
1
(Faculty of Chemistry, University of Bu-Ali Sina, 65178, Hamedan, Iran.)
Mohammad Ali Zolfigol
2
(Faculty of Chemistry, University of Bu-Ali Sina, 65178, Hamedan, Iran.)
Toktam Faal Rastegar
3
(Faculty of Chemistry, University of Bu-Ali Sina, 65178, Hamedan, Iran.)
Gholamabbas Chehardoli
4
(School of Pharmacy, University of Medical Sciences, Hamedan 65178, Iran.)
Shadpour Mallakpour
5
(Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan, Iran.
Nanotechnology and Advanced Materials Institute, Isfahan University of Technology, Isfahan, Iran.)
الکلمات المفتاحية: 1, Dimedone, Aldehyde, Multi-component reaction, Melamine trisulfonic acid (MTSA), Urazole, 3-cyclohexanedione, Phthalhydrazide,
ملخص المقالة :
Melamine trisulfonic acid (MTSA) as an efficient heterogeneous catalyst has been used for the one-pot preparation of triazolo[1,2-a]indazole-1,3,8-trione and 2H-indazolo[2,1-b]phthalazine-1,6,11-trione derivatives by the three-component condensation reaction of urazoles or phthalhydrazide, dimedone or 1,3-cyclohexanedione, and aldehydes under solvent-free conditions in good to excellent yields and short reaction times.
[1] (a) J. Zhu, H. Bienaym-e, Multicomponent Reactions; Wiley-VCH: Weinheim, Germany, 2005; (b) A. Domling, I. Ugi, Angew. Chem. Int. Ed., 39 (2000) 3168-3210.
[2] A. Domling, Chem. Rev., 106 (2006) 17-89.
[3] G. Sartori, R. Ballini, F. Bigi, G. Bosica, R. Maggi, P. Righi, Chem. Rev., 104 (2004) 199-250.
[4] (a) X. Lei, N. Zaarur, M.Y. Sherman, J.A. Jr. Porco, J. Org. Chem. 70 (2005) 6474-6483; (b) A. Kiriazis, T. Ruffer, S. Jantti, H. Lang, J. Yli-Kauhaluama, J. Comb. Chem., 9 (2007) 263-266; (c) P.D. Boatman, J. Urban, M. Nguyen, M. Qabar, M. Kahn, Bioorg. Med. Chem. Lett., 13 (2003) 1445-1449; (d) V.M. Kolb, J.P. Dworkin, S.L. Miller, J. Mol. Evol., 38 (1994) 549-557; (e) R.A. Izydore, J.A. Bernal-Ramirez, P. Singh, J. Org. Chem., 55 (1990) 3761-3767.
[5] (a) F. Al´-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan, B.A. Chakchir, Pharm. Chem. J., 36 (2002) 598-603; (b) R.P. Jain, J.C. Vederas, Bioorg. Med. Chem. Lett., 14 (2004) 3655-3658; (c) R.W. Carling, K.W. Moore, L.J. Street, D. Wild, C. Isted, P.D. Leeson, S. Thomas, D. O’Conner, R.M. McKernan, K. Quirk, S.M. Cook, J.R. Atack, K.A. Waftord, S.A. Thompson, G.R. Dawson, P. Ferris, J.L. Castro, J. Med. Chem., 47 (2004) 1807-1822.
[6] (a) M. Sayyafi, M. Seyyedhamzeh, H.R. Khavasi, A. Bazgir, Tetrahedron, 64 (2008) 2375-2378; (b) H.R. Shaterian, M. Ghashang, M. Feyzi, Applied Catalysis A: General, 345 (2008) 128-133; (c) H.R. Shaterian, A. Hosseinian, M. Ghashang, ARKIVOC, 2 (2009) 59-67; (d) J.M. Khurana, D. Magoo, Tetrahedron Lett., 50 (2009) 7300-7303; (e) M. Adharvana Chari, G. Karthikeyan, A. Pandurangan, T. Siddulu Naidu, B. Sathyaseelan, S.M. Javaid Zaidi, A. Vinu, Tetrahedron Lett., 51 (2010) 2629-2632; (f) A. Hasaninejad, A. Zare, M. Shekouhy, Tetrahedron, 67 (2011) 390-400; (g) D. Azarifar, R. Nejat-Yami, Z. Akrami, F. Sameri, S. Samadi, Lett. Org. Chem., 9 (2012) 128-132; (h) A. Bazgir, M. Seyyedhamzeh, Z. Yasaei, P. Mirzaei, Tetrahedron Lett., 48 (2007) 8790-8794; (i) R. Ghorbani-Vaghei, R. Karimi-Nami, Z. Toghraei-Semiromi, M. Amiri, M. Ghavidel, Tetrahedron Lett., 67 (2011) 1930-1937; (j) G. Shukla, R.K. Verma, G.K. Verma, M.S. Singh, Tetrahedron Lett., 52 (2011) 7195-7198; (k) M. Kidwai, A. Jahan, R. Chauhan, N.K. Mishra, Tetrahedron Lett., 53 (2012) 1728-1731; (l) H. Hamidian, S. Fozooni, A. Hassankhani, S.Z. Mohammadi, Molecules, 16 (2011) 9041-9048; (m) A. Hassankhani, E. Mosaddegh, S.Y. Ebrahimipour, Arabian J. Chem., 2011, doi:10.1016/j.arabjc.2011. 10.003; (n) M.V. Reddy, G.C.S. Reddy, Y.T. Jeong, Tetrahedron, 68 (2012) 6820-6828.
[7] G. Chehardoli, M.A Zolfigol, T. Faal-Rastegar, S.Mallakpour, A. Ghorbani-Choghamarani, J. Chem. Sci., 121 (2009) 441-447.
[8] (a) S.E. Mallakpour, M.A. Zolfigol, Indian J. Chem., 34B (1995) 183-189; (b) S.E. Mallakpour, M.A. Zolfigol, Indian J. Chem., 34B (1995) 302-309; (c) S.E. Mallakpour, M.A. Zolfigol, Indian J. Chem., 37B (1995) 1001-1006; (d) S.E. Mallakpour, M.A. Zolfigol, Indian J. Chem., 38B (1999) 777-782; (e) S.E. Mallakpour, M.A. Zolfigol, J. Sci. I. R. Iran, 4 (1993) 199-205; (f) S.E. Mallakpour, J. Chem. Educ., 69 (1992) 238-241; (g) S.E. Mallakpour, Z. Rafiee, Synlett, (2007) 1255–1256; (h) S.E. Mallakpour, Z. Rafiee, Synth. Commun., 37 (2007) 1927-1934.
[9] (a) P. Salehi, M.A. Zolfigol, F. Shirini, M. Baghbanzadeh, Curr. Org. Chem., 10 (2006) 2171-2189; (b) F. Shirini, M.A. Zolfigol, P. Salehi, M. Abedini, Curr. Org. Chem., 12 (2008) 183-202; (c) M.A. Zolfigol, I. Mohammadpoor-Baltork, M. Shiri, J. Iran Chem. Soc., 5 (2008) 90-95; (d) A. Bamoniri, B.F. Mirjalili, M.A. Zolfigol, I. Mohammadpoor-Baltork, J. Iran Chem. Soc., 4 (2007) 332-335; (e) A. Bamoniri, M.A. Zolfigol, I. Mohammadpoor-Baltork, B.F. Mirjalili, J. Iran. Chem. Soc., 3 (2006) 85-88; (f) K. Niknam, M.A. Zolfigol, T. Sadabadi, A. Nejati, J. Iran. Chem. Soc., 3 (2006) 318-322.
[10] (a) F. Shirini, M.A. Zolfigol, J. Albadi, T. Faal-Rastegar, Iran. J. Catal., 1 (2011) 11-17; (b) F. Shirini, M.A. Zolfigol, A.R.Aliakbar, J. Albadi, Synth. Commun., 40 (2010) 1022-1028; (c) F. Shirini, M.A. Zolfigol, J. Albadi, Synth. Commun., 40 (2010) 910-914; (d) F. Shirini, J. Albadi, Bull. Korean Chem. Soc., 31 (2010) 1119-1120; (e) F. Shirini, M.A. Zolfigol, J. Albadi, J. Iran. Chem. Soc., 7 (2010) 895-899; (f) F. Shirini, M.A. Zolfigol, J. Albadi, Chin. Chem. Lett., 22 (2011) 318-321; (g) W. Ma, X. Wang, F. Yan, L. Wu, Y. Wang, Monatsh Chem., 142 (2011) 163-167; (h) X. Shang, M. Geng, L. Wu, Asian J. Chem., 24 (2012) 515-517; (i) L. Wu, Y. Yan, F. Yan, Phosphorus, Sulfur Silicon Relat. Elem., 187 (2012) 149-154; (j) L. Wu, P. Sun, F. Yan, Phosphorus, Sulfur Silicon Relat. Elem., 186 (2011) 2055-2060; (k) W. Li, Q. Luo, E-J. Chem., 8 (2011) 1972-1978.
