Enhanced catalytic activity of Zr(IV) complex with simple tetradentate Schiff base ligand in the clean synthesis of indole derivatives

Inorganic Chemistry Communications

Volumn 14, Issue 11, 2011, Pages 1732-1736

  Jafarpour, Maasoumeh ^a   Rezaeifard, Abdolreza ^a   Gorzin, Ghorbanali ^a  

^a UNIVERSITY OF BIRJAND   (Iran)

Author keywords

Indole derivatives; Salphen; Schiff base; Zirconium complexes

Indexed keywords

EID: 80053566989     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2011.07.017     Document Type: Article

References (46)

1. C. Gil, and S. Brase Solid-phase synthesis of biologically active benzoannelated nitrogen heterocycles: an update J. Comb. Chem. 11 2009 175 197
2. J. Barluenga, F. Rodriguez, and F.J. Fananas Recent advances in the synthesis of indole and quinoline derivatives through cascade reactions Chem. Asian J. 4 2009 1036 1048
3. K. Kruger, A. Tillack, and M. Beller Catalytic synthesis of indoles from alkynes Adv. Synth. Catal. 350 2008 2153 2167
4. J.J. Song, J.T. Reeves, F. Gallou, Z.L. Tan, N.K. Yee, and C.H. Senanayake Organometallic methods for the synthesis and functionalization of azaindoles Chem Soc. Rev. 36 2007 1120 1132
5. S. Patil, and R. Patil Synthesis and functionalization of indoles through rhodium-catalyzed reactions Curr. Org. Synth. 4 2007 201 222
6. J. Hajicek A review on recent developments in syntheses of the post-secodine indole alkaloids. Part II: Modified alkaloid types Collect Czech. Chem. Commun. 72 2007 821 898
7. S. Patil, and J.K. Buolamwini Recent uses of palladium chemistry in indole synthesis Curr Org. Synth. 3 2006 477 498 (Pubitemid 44697182)
8. G.R. Humphrey, and J.T. Kuethe Practical methodologies for the synthesis of indoles Chem Review 106 2006 2875 2911 (Pubitemid 44193050)
9. S. Cacchi, and G. Fabrizi Synthesis and functionalization of indoles through palladium-catalyzed reactions Chem Review 105 2005 2873 2920 (Pubitemid 41046993)
10. S. Agarwal, S. Cammerer, S. Filali, W. Frohner, J. Knoll, M.P. Krahl, K.R. Reddy, and H.J. Knolker Novel routes to pyrroles, indoles and carbazoles - applications in natural product synthesis Curr. Org. Chem. 9 2005 1601 1614 (Pubitemid 41264303)
11. M.A. Metwally, S. Shaaban, B.F. Abdel-Wahab, and G.A. El-Hiti 3-acetylindoles: synthesis, reactions and biological activities Curr Org. Chem. 13 2009 1475 1496
12. M. Bandini, and A. Eichholzer Catalytic functionalization of indoles in a new dimension Angew Chem. Int. Ed. 48 2009 9608 9644
13. W.H. Leung, E.Y.Y. Chan, E.K.F. Chow, I.D. Williams, and S.M. Peng Metal complexes of a chiral quadridentate Schiff base J. Chem. Soc., Dalton Trans. 1996 1229 1236 (Pubitemid 126842007)
14. M. Pasquali, F. Marchetti, A. Landi, and C. Floriani Preparations and structures of NN′-ethylenebis(salicylideneiminato)-titanium(III) derivatives J. Chem. Soc., Dalton Trans. 1978 545 549
15. G. Dellamico, F. Marchetti, and C. Floriani Peripheral electrophilic properties of dichloro[NN′-ethylenebis(salicylideneiminato)]titanium(IV): a route leading to a stable Ti-H-B unit J. Chem. Soc., Dalton Trans. 1982 2197 2202
16. 2] [acen = N,N′- ethylenebis(acetylacetoneiminate) J. Chem. Soc., Dalton Trans. 1990 1345 1355
17. J. Huang, B. Lian, L. Yong, and Y. Qian Syntheses of zirconium (IV) complexes with Schiff-base ligand and their catalytic activities for polymerization of ethylene Inorg Chem. Commun. 4 2001 392 394 (Pubitemid 32641037)
18. C. Floriani Early transition metal-schiff base complexes: from structure to reactivity Polyhedron 8 1989 1717 1722
19. J. Rosset, C. Floriani, M. Mazzanti, A. Chiesi-Villa, and C. Guastini Vanadium(III)-carbon and titanium(III)-carbon functionalities supported by a tetradentate Schiff base ligand Inorg. Chem. 29 1990 3991 3996
20. E. Solari, C. Floriani, A. Chiesi-Villa, and C. Rizzoli Alkylation and arylation of dichloro[N,N′-ethylenebis(salicylideneiminato)]titanium(IV) J. Chem. Soc., Dalton Trans. 1992 367 373
21. E. Solari, C. Maltese, F. Franceschi, C. Floriani, A. Chiesi-Villa, and C. Rizzoli Geometrical isomerism and redox behaviour in zirconium-Schiff base complexes: The formation of C-C bonds functioning as two-electron reservoirs J. Chem. Soc., Dalton Trans. 1997 2903 2910 (Pubitemid 127780646)
22. A. Watanabe, T. Uchida, K. Ito, and T. Katsuki Highly enantioselective Baeyer-Villiger oxidation using Zr(salen) complex as catalyst Tetrahedron Lett. 43 2002 4481 4485 (Pubitemid 34615850)
23. M. Jafarpour, A. Rezaeifard, and M. Aliabadi Zirconium tetrakis(dodecylsulfate) as an efficient and recyclable lewis acid-surfactant-combined catalyzed C-C and C-N bond forming under mild and environmentally benign conditions Lett. Org. Chem. 6 2009 94 99
24. M. Jafarpour, A. Rezaeifard, and T. Golshani A new catalytic method for ecofriendly synthesis of bis- and trisindolylmethanes by zirconyldodecylsulfate under mild conditions J. Heterocycl. Chem. 46 2009 535 539
25. M. Jafarpour, A. Rezaeifard, and M. Aliabadi An environmentally benign catalytic method for efficient and selective nucleophilic ring opening of oxiranes by zirconium tetrakis(dodecyl sulfate) Helv Chem. Acta 93 2010 405 413
26. M. Jafarpour, A. Rezaeifard, T. Golshani, and A. Green Catalyst-free method for the synthesis of sulfonamides and sulfonylazides Phosphorus, Sulfur, Silicon Relat Elem. 186 2011 140 148
27. 4 dispersed on dry silica gel provides a useful reagent for S-alkylation of thiols with alcohols under solvent-free conditions Tetrahedron Lett. 47 2006 93 97 (Pubitemid 41743783)
28. 2O/silica gel as a new efficient and a highly water-tolerant catalyst system for facile condensation of indoles with carbonyl compounds under solvent-free conditions J. Mol. Catal. A. 253 2006 249 251 (Pubitemid 43783429)
29. H. Firouzabadi, N. Iranpoor, M. Jafarpour, and A. Ghaderi Silica gel catalyzed highly selective CS bond formation via Michael addition of thiols to α, β-unsaturated ketones under solvent-free conditions J. Mol. Catal. A. 249 2006 98 102
30. M. Jafarpour, A. Rezaeifard, and M. Aliabadi Catalytic activity of silica gel in the synthesis of sulfonamides under mild and solvent-free conditions Appl. Catal. A: Gen. 358 2009 49 53
31. M. Jafarpour, A. Rezaeifard, and M. Danehchin Easy access to quinoxaline derivatives using alumina as an effective and reusable catalyst under solvent-free conditions Appl. Catal. A: Gen. 394 2011 48 51
32. M. Jafarpour, A. Rezaeifard, and M. Heidari Efficient organic transformations mediated by ZrOCl2•8H2O in water Phosphorus, Sulfur, Silicon 186 2011 1 13
33. M. Jafarpour, A. Rezaeifard, and M. Heidari A new catalytic method for eco-friendly synthesis of quinoxalines by zirconium (IV) oxide chloride octahydrate under mild conditions Lett. Org. Chem. 8 2011 202 209
34. H. Firouzabadi, and M. Jafarpour Some applications of zirconium(IV) tetrachloride (ZrCl4) and zirconium(IV) oxydichloride octahydrate (ZrOCl2.8H2O) as catalysts or reagents in organic synthesis J. Iran. Chem. Soc. 5 2008 159 183
35. Ł. Gorski, A. Saniewska, P. Parzuchowski, M.E. Meyerhoff, and E. Mali Zirconium(IV)-salophens as fluoride-selective ionophores in polymeric membrane electrodes Anal. Chim. Acta 551 2005 37 44 (Pubitemid 41393996)
36. See references cited in H. Alinezhad, A.H. Haghighi, and F. Salehian A green method for the synthesis of bis-indolylmethanes and 3,3′- indolyloxindole derivatives using cellulose sulfuric acid under solvent-free conditions Chin. Chem. Lett. 21 2010 183 186
37. R.R. Nagawade, and D.B. Shinde Zirconium(IV) chloride - catalysed reaction of indoles: an expeditious synthesis of bis(indolyl)methanes Bull. Korean Chem. Soc. 26 2005 1962 1964 (Pubitemid 43175431)
38. R.R. Nagawade, and D.B. Shinde Zirconyl(IV) chloride - catalysed reaction of indoles: an expeditious synthesis of bis(indolyl)methanes Acta Chim. Slov. 53 2006 210 213 (Pubitemid 44060521)
39. D. Chen, L. Yu, and P.G. Wang Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones Tetrahedron Lett. 37 1996 4467 4470 (Pubitemid 26257349)
40. M.B. Teimouri, and H. Mivehchi Efficient hexamethylenetetramine-bromine (HMTAB)-catalyzed synthesis of bis(indolyl)methanes in water Synth. Commun. 35 2005 1835 1843 (Pubitemid 40967565)
41. III-catalyzed synthesis of Bis(indolyl)methanes in ionic liquids Eur. J. Org. Chem. 2004 1584 1587
42. N. Azizi, L. Torkian, and M.R. Saidi Highly efficient synthesis of bis(indolyl)methanes in water J. Mol. Catal. A 275 2007 109 112 (Pubitemid 47332258)
43. J.S. Yadav, B.V.S. Reddy, V.S.R. Murthy, G.M. Kumar, and C. Madan Lithium perchlorate catalyzed reactions of indoles: an expeditious synthesis of bis(indolyl)methanes Synthesis 2001 783 787 (Pubitemid 32378560)
44. 2)-catalyzed expedient, solventless and mild synthesis of bis(indolyl)methanes Acta Chim. Slov. 54 2007 354 359
45. K. Niknam, M.A. Zolfigol, T. Sadabadi, and A. Nejati Preparation of indolylmethanes catalyzed by metal hydrogen sulfates J. Iran. Chem. Soc. 3 2006 318 322
46. S. Palaniappan, and A. John Facile synthesis of bis(indolyl)methanes using polyindole salt as reusable catalyst J. Mol. Catal. A 242 2005 168 172 (Pubitemid 41607936)