Abstract
1,1′-Butylenebis(3-methyl-3H-imidazol-1-ium) hydrogen sulfate as an efficient, halogen-free, and reusable binuclear Brønsted ionic liquid catalyzed the synthesis of tacrine analogues. This method has the advantages of high yield, clean reaction, and simple methodology. The structure of the products was confirmed by IR, 1H NMR, 13C NMR, MS, and elemental analysis.
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Shaw FH, Bentley G (1953) Aust J Exp Biol Med Sci 31:573
Heilbronn E (1961) Acta Chem Scand 15:1386
Maayani S, Weinstein H, Ben-Zvi N, Cohen S, Sokolovsky M (1974) Biochem Pharmacol 23:1263
Summers WK, Majovski LV, Marsh GM, Tachiki K, Kling A (1986) N Engl J Med 315:1241
Wurtman RJ (1985) Sci Am 252:48
Altman HJ (ed) (1987) Alzheimer’s diseases problems prospects and perspectives. Plenum Press, New York
Francotte P, Graindorge E, Boverie S, de Tullio P, Pirotte B (2004) Curr Med Chem 11:1757
Watkins PB, Zimmerman HJ, Knapp MJ, Gracon SI, Lewis KW (1994) J Am Med Assoc 271:992
Ames DJ, Bhathal PS, Davies BM, Fraser JRE, Gibson PR, Roberts S (1990) N Z J Med 20:193
Cavalli A, Bolognesi ML, Minarini A, Rosini M, Tumiatti V, Recanatini M, Melchiorre C (2008) J Med Chem 51:347
Harvey AL, Rowan EG (1988) Action of THA, 3,4-diaminopyridine, physostigmine and galanthamine on neuronal K+ currents at a cholinergic nerve terminal. In: Giacobini E, Becker R (eds) Current Research in Alzheimer Therapy. Taylor and Francis, New York
McKenna MT, Proctor GR, Young LC, Harvey AL (1997) J Med Chem 40:3516
Drukarch B, Leysen JE, Stoof JC (1988) Life Sci 42:1011
Sokhwinder J, Adem A, Winblad B, Oreland L (1992) Pharmacol Toxicol 71:213
Kaul PN (1962) J Pharm Pharmacol 14:243
Neilsen JA, Mena EE, Williams IH, Nocerine MR, Liston D (1988) Eur J Pharmacol 173:53
McNally W, Roth M, Young R, Bockbrader H, Chang T (1989) Pharm Res 924
Chaki H, Yamabe H, Sugano M, Morita S, Bessho T, Tabata R, Saito KI, Egawa M, Tobe A, Morinaka Y (1995) Bioorg Med Chem Lett 5:1495
Thomae D, Kirsch G, Seck P (2007) Synthesis 1027
Michalson ET, D’Andrea S, Freeman JP, Szmuszkovicz J (1999) Heterocycles 30:415
Marco JL, Rios C, Garcia AG, Villarroya M, Carreiras MC, Martins C, Eleutério A, Morreale A, Orozco M, Luque F (2004) Bioorg Med Chem 12:2199
Barreiro EJ, Camara CA, Verli H, Brazil-Mas L, Castro NG, Cintra WM, Aracava Y, Fraga CAM (2003) J Med Chem 46:1144
Shao D, Zou C, Luo C, Tang X, Li Y (2004) Bioorg Med Chem Lett 14:4639
Alonso D, Dorronsoro I, Rubio L, Munõz P, García-Palomero E, Del Monte M, Bidon-Chanal A, Orozco M, Luque FJ, Castro A, Medina M, Martínez A (2005) Bioorg Med Chem 13:6588
Camps P, Formosa X, Galdeano C, Gómez T, Munõz-Torrero D, Scarpellini M, Viayna E, Badia A, Clos MV, Camins A, Pallàs M, Bartolini M, Francesca Mancini F, Andrisano V, Estelrich J, Lizondo M, Bidon-Chanal A, Luque FJ (2008) J Med Chem 51:3588
Yang L, Li J, Chai H, Lu H, Zhang Q, Shi D (2013) Chin J Chem 31:443
Khaligh NG (2014) Chin J Catal 35:1036
Khaligh NG (2014) Res Chem Intermed. doi:10.1007/s11164-014-1642-5
Cole AC, Jensen JL, Ntai I, Tran KLT, Weaver KJ, Forbes DC, Davis JH Jr (2002) J Am Chem Soc 124:5962
Arfan A, Bazureau JP (2005) Org Process Res Dev 9:743
Wasserscheid P, Sesing M, Korth W (2002) Green Chem 4:134
Seddon KR, Stark A, Torres MJ (2000) Pure Appl Chem 72:2275
Fraga-Dubreuil J, Bourahla K, Rahmouni M, Bazureau JP, Hamelin J (2002) Catal Commun 3:185
Gu Y, Zhang J, Duan Z, Deng Y (2005) Adv Synth Catal 347:512
Kalita P, Kumar R (2012) Microporous Mesoporous Mater 149:1
Khaligh NG (2014) Monatsh Chem 145:1643
McKenna MT, Proctor GR, Young LC, Harvey AL (1997) J Med Chem 40:3516
Da Costa JS, Pisoni DS, Da Silva CB, Petzhold CL, Russowsky D, Ceschi MA (2009) J Braz Chem Soc 20:1448
Yang D, Jiang K, Li J, Xu F (2007) Tetrahedron 63:7654
Proctor GR, Harvey AL (2000) Curr Med Chem 7:295
Hafelinger G, Steinmann L (1977) Angew Chem Int Ed 16:47
OECD Chemical Group (1993) Ready biodegradability: modified OECD screening test. Method 301 E. OECD revised guidelines for tests for ready biodegradability, Paris
Gathergood N, Garcia MT, Scammells PJ (2004) Green Chem 6:166
Garcia MT, Gathergood N, Scammells PJ (2005) Green Chem 7:9
APHA (American Public Health), AWWA (American Water Works Association), and WPCF (Water Pollution Control Federation) (1985) Method 508B, standard methods for the examination of water and wastewater, 16th edn. Washington, p 532
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I am grateful to Research House of Professor Reza, Education Guilan for partial support of this work.
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Ghaffari Khaligh, N. 1,1′-Butylenebis(3-methyl-3H-imidazol-1-ium) hydrogen sulfate as an efficient binuclear Brønsted ionic liquid for the synthesis of tacrine analogues . Monatsh Chem 146, 321–326 (2015). https://doi.org/10.1007/s00706-014-1325-3
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DOI: https://doi.org/10.1007/s00706-014-1325-3