Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2016; 27(10): 1527-1530
DOI: 10.1055/s-0035-1560425
DOI: 10.1055/s-0035-1560425
letter
Solid-Supported Synthesis of Flexible Dimeric Pyridinium Salts and Their Catalytic Activities
Further Information
Publication History
Received: 27 December 2015
Accepted after revision: 05 February 2016
Publication Date:
24 March 2016 (online)
Abstract
The synthesis of flexible dimeric pyridinium ionic liquids by both conventional and solid-supported approaches are described. We have optimized the Biginelli reaction with various concentrations of our synthesized ionic liquids with various counter ions. Among these, bromide-containing ionic liquids showed best catalytic activity.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560425.
- Supporting Information
-
References and Notes
- 1 Peng J, Deng Y. Tetrahedron Lett. 2001; 42: 5917
- 2a Dondoni A, Massi A. Acc. Chem. Res. 2006; 39: 451
- 2b Aron ZD, Overman LE. Chem. Commun. 2004; 253
- 2c Kappe CO. Acc. Chem. Res. 2000; 33: 879
- 3 Biginelli P. Gazz. Chim. Ital. 1893; 23: 360
- 4a Polshettiwar V, Varma RS. Tetrahedron Lett. 2007; 48: 7343
- 4b Kumar A, Maurya RA. Synlett 2008; 883
- 5 Patil AD, Kumar NV, Kokko WC, Bean MF, Freyer AJ, Debrosse C. J. Org. Chem. 1995; 60: 1182
- 6a Abdel Hafez OM, Amin KM, Abdel-Latif NA, Mohamed TK, Ahmed EY, Maher T. Eur. J. Med. Chem. 2009; 44: 2967
- 6b Kempen I, Papapostolou D, Thierry N, Pochet L, Counerotte S, Masereel B, Foidart J-M, Reboud-Ravaux M, Noel A, Pirotte B. Br. J. Cancer 2003; 88: 1111
- 7 Rovnyak GC, Atwal KS, Hedberg A, Kimball SD, Moreland S, Gougoutas JZ, O’Reilly BC, Schwartz J, Malley MF. J. Med. Chem. 1992; 35: 3254
- 8 Okabe M, Sun RC, Zenchoff GB. J. Org. Chem. 1991; 56: 4393
- 9a Stanchev S, Hadjimitova V, Traykov T, Boyanov T, Manolova I. Eur. J. Med. Chem. 2009; 44: 3077
- 9b Xiao C, Song Z.-G, Liu Z.-Q. Eur. J. Med. Chem. 2010; 45: 2559
- 10 Brown DJ, Evans RF, Cowden WB, Fenn MD. Chemistry of Heterocyclic compounds: The Pyrimidines: Supplement II. John Wiley & Sons; New York: 1985. Vol. 16
- 11 Ramesh B, Bhalgat CM. Eur. J. Med. Chem. 2011; 46: 1882
- 12 Neto AD, Spencer J. J. Braz. Chem. Soc. 2012; 23: 987
- 13 Isambert N, Duque MD. S, Plaquevent JC, Genisson Y, Rodriguez J, Constantieux T. Chem. Soc. Rev. 2011; 40: 1347
- 14a Manikandan C, Ganesan K. Synth. Commun. 2014; 44: 3362
- 14b Ganapathi P, Ganesan K. Synth. Commun. 2015; 45: 2135
- 14c Naveenkumar R, Ganapathi P, Ganesan K. J. Heterocycl. Chem. 2016; in press; DOI: 10.1002/jhet.2538
-
15 Yu J, Shi F, Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156
- 16 Dondoni A, Massi A. Acc. Chem. Res. 2006; 39: 451
- 17 2,2′-(Butane-1,4-diyl)bis(oxy)dipyridinium Benzylbromide (2a) Yield 5.9 g 90%; liquid. 1H NMR (400 MHz, CDCl3): δ = 3.45 (t, 4 H), 4.01 (q, 4 H), 5.23 (s, 4 H), 8.18–8.22 (m, 8 H), 7.28–7.58 (m, 10 H). 13C NMR (100 MHz, CDCl3): δ = 26.1, 51.8, 106.8, 121.1, 124.0, 128.5, 129.9, 137.7, 140.0, 144.7, 147.6. MS: m/z = 586.36. Anal. Calcd for C28H30Br2N2O2: C, 57.30; H, 5.11; N, 4.77. Found: C, 57.18; H, 5.04; N, 4.66.
- 18 2,2′-(Butane-1,4-diylbis(oxy)dipyridinium Benzylhexafluorophosphate (3a) Yield 0.78 g, 91%; liquid. 1H NMR (400 MHz, CDCl3): δ = 3.50 (t, 4 H), 4.03 (q, 4 H), 5.27 (s, 4 H), 8.20–8.27 (m, 8 H), 7.30–7.60 (m, 10 H). 13C NMR (100 MHz, CDCl3): δ = 26.5, 51.1, 106.5, 121.3, 124.2, 128.8, 129.1, 137.4, 140.1, 144.9, 147.4. MS: m/z = 716.48. Anal. Calcd for C28H30F12N2O2P2: C, 46.89; H, 4.18; N, 3.90. Found: C, 46.81; H, 4.09; N, 3.82.
- 19 Zhang L, Zhang Z, Liu Q, Liu T, Zhang G. J. Org. Chem. 2014; 79: 2281
- 20 Shen Z, Xu X, Ji S. J. Org. Chem. 2010; 75: 1162
- 21 Chandra Nandi G, Samai S, Singh M. J. Org. Chem. 2010; 75: 7785
- 22 Fuchs D, Nasr-Esfahani M, Diab L, Mejkal T, Breit B. Synlett 2013; 24: 1657