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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 18
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Original Articles

Sulfonic acid–functionalized Wang resin (Wang-OSO3H) as polymeric acidic catalyst for the ecofriendly multicomponent synthesis of polyhydroquinolines via Hantzsch condensation

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Pages 1519-1528 | Received 23 May 2016, Published online: 10 Sep 2016

References

  • (a) Mauzeral, D.; Westheimer, F. H. J. Am. Chem. Soc. 1955, 77, 2261; (b) Baraldi, P. G.; Chiarini, A.; Budriesi, R.; Roberti, M.; Casolar, A.; Manfredini, S.; Simoni, D.; Zanirato, V.; Varani, K.; Borea, P. A. Drug Des. Deliv. 1989, 5, 13; (c) Baraldi, P. G.; Budriesi, R.; Cacciari, B.; Chiarini, A.; Garuti, L.; Giovanninetti, G.; Leoni, A.; Roberti, M. Collect. Czech. Chem. Commun. 1992, 169; (d) Di Stilo, A.; Visentin, S.; Clara, C.; Gasco, A. M.; Ermondi, G.; Gasco, A. J. Med. Chem. 1998, 41, 5393; (e) Kawase, M.; Shah, A.; Gaveriya, H.; Motohashi, N.; Sakagami, H.; Varga, A.; Molnar, J. J. Bioorg. Chem. 2002, 10, 1051; (f) Suarez, M.; Verdecia, Y.; Illescas, B.; Martinez-Alvarez, R.; Avarez, A.; Ochoa, E.; Seoane, C.; Kayali, N.; Martin, N. Tetrahedron 2003, 59, 9179.
  • (a) Reid, J. L.; Meredith, P. A.; Pasanisi, F. J. Cardiovasc. Pharmacol. 1985, 7, S18; (b) Buhler, F. R.; Kiowski, W. J. Hypertens. 1987, 5, S3.
  • Loev, B.; Snader, K. M. J. Org. Chem. 1965, 30, 1914–1916.
  • (a) Godfraid, T.; Miller, R.; Wibo, M. Pharmacol. Rev. 1986, 38, 321; (b) Sausins, A.; Duburs, G. Heterocycles 1988, 27, 269; (c) Mager, P. P.; Coburn, R. A.; Solo, A. J.; Triggle, D. J.; Rothe, H. Drug Des. Discov. 1992, 8, 273; (d) Mannhold, R.; Jablonka, B.; Voigdt, W.; Schoenafinger, K.; Schravan, K. Eur. J. Med. Chem. 1992, 27, 229.
  • (a) Bretzel, R. G.; Bollen, C. C.; Maeser, E.; Federlin, K. F. Drugs Future 1992, 17, 465; (b) Bretzel, R. G.; Bollen, C. C.; Maeser, E.; Federlin, K. F. Am. J. Kidney Dis. 1993, 21, 53; (c) Klusa, V. Drugs Future 1995, 20, 135; (d) Boer, R.; Gekeler, V. Drugs Future 1995, 20, 499.
  • Kumar, S.; Sharma, P.; Kapoor, K. K.; Hundal, M. S. Tetrahedron 2008, 64, 536–542.
  • Mekheimer, R. A.; Hameed, A. A.; Sadek, K. U. Green Chem. 2008, 10, 592–593.
  • Jiang, S. J.; Lu, Z. Q.; Loa, J. Synlett 2004, 831.
  • Zhang, X. Y.; Li, Y. Z.; Fan, X. S.; Qu, G. R.; Hu, X. Y.; Wang J. J. Chin. Chem. Lett. 2006, 17, 150.
  • Tewari, N.; Dwivedi, N.; Tripathi, R. P. Tetrahedron Lett. 2004, 45, 9011.
  • Sharma, G. V. M.; Reddy, K. L.; Lakshmi, P. S.; Krishna, P. R. Synthesis 2006, 55.
  • Heravi, M. M.; Bakhtiari, K.; Javadi, N. M.; Bamoharram, F. F.; Saeedi, M.; Oskooie, H. O. J. Mol. Catal. A: Chem. 2007, 264, 50.
  • Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C. F. Tetrahedron Lett. 2005, 46, 5771–5774; (b) Hong, M.; Chai, C.; Yi, W. B. J. Fluorine Chem. 2010, 131, 111–114.
  • Maheswara, M.; Siddaiah, V.; Rao, Y. K.; Tzeng, Y. M.; Sridhar, C. J. Mol. Catal. A: Chem. 2006, 260, 179.
  • Gupta, R.; Paul, S.; Loupy, A. Synthesis 2007, 2835.
  • (a) Maheswara, M.; Siddaiah, V.; Venkata Rao, C. Arkivoc 2006, 2, 201–206; (b) Sainani, J. B.; Shah, A. C.; Arya, V. P. Indian J. Chem, Sect. B 1994, 33, 526; (c) Ji, S. J.; Jiang, Z. Q.; Lu, J.; Loa, T. P. Synlett 2004, 831.
  • Sabitha, G.; Reddy, G. S. K.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2003, 44, 4129–4131.
  • Kassaee, M. Z.; Masrouri, M.; Movahedi, F. Monatsch. Chem. 2010, 14, 317.
  • Donelson, J. L.; Gibbs, R. A.; De, S. K. J. Mol. Catal. A: Chem. 2006, 256, 309.
  • Das, B.; Ravikanth, B.; Ramu, R.; Vittal Rao, B. Chem. Pharm. Bull. 2006, 54, 1044.
  • Cherkupally, S. R.; Mekalan, R. Chem. Pharm. Bull. 2008, 56, 1002.
  • (a) Li, M.; Zuo, Z.; Wen, L.; Wang, S. J. J. Comb. Chem. 2008, 10, 436; (b) Tu, S. J.; Zhou, J. F.; Deng, X.; Cai, P. J.; Wang, H.; Feng, J. C. Chin. J. Org. Chem. 2001, 21, 313.
  • Undale, K. A.; Shaikh, T. S.; Gaikwad, D. S.; Pore, D. M. Chim. 2011, 14, 511.
  • Adude, R. N.; Goswami, S. V.; Bhusare, S. R. Int. J. Indust. Chem. 2012, 3, 6.
  • Rajnarendra, E.; Reddy, M. N.; Raju, S. Ind. J. Chem. 2011, 50B, 751.
  • Heravi, M. M.; Pooremamy, S.; Oskooie, H. A. Synth. Commun. 2011, 41, 113.
  • (a) Ghodsi, M. Z.; Yeganeh, K.; Mehbobeh, H. Iran. J. Chem. Chem. Eng. 2010, 29.
  • (a) Maleki, A. Tetrahedron Lett. 2013, 54, 2055–2059; (b) Maleki, A. Tetrahedron Lett. 2012, 68, 7827–7833; (c) Maleki, A.; Rahimi, R.; Maleki, S.; Hamidi, N. RSC Adv. 2014, 4, 29765–29771; (d) Maleki, A.; Alrezvani, Z.; Maleki, S. Catal. Commun. 2015, 69, 29–33.
  • Maleki, A. RSC Adv. 2014, 4, 64169–64173.
  • Maleki, A.; Akhlaghi, E.; Paydar, R. Appl. Organometal. Chem. 2016, 30, 382–386.
  • (a) Hong, M.; Chai, C.; Yi, W.-B. J. Fluorine Chem. 2010, 131, 1, 111–114; (b) Ji, S.; Jiang, Z.-Q.; Lu, J.; Loh, T.-P. Synlett 2004, 5, 831–835; (c) Kumar, A.; Maurya, R. A. Synlett 2008, 6, 883–885; (d) Surasani, R.; Kalita, D.; Dhanunjaya Rao, A. V.; Yarbagi, K.; Chandrasekhar, K. B. J. Fluorine Chem. 2012, 135, 91–96.
  • (a) Wang, S. J. Am. Chem. Soc. 1973, 95, 1328; (b) Dhanunjaya Rao, A. V.; Vykunteswararao, B. P.; Bhaskarkumar, T.; Jogdand, N. R.; Kalita, D.; Lilakar, J. K. D.; Siddaiah, V.; Sanasi, P. D.; Raghunadh, A. Tetrahedron Lett. 2015, 56, 4714–4717; (c) Wen, X. Indian J. Chem., 2006, 45B, 762–765.
  • Preparation of Wang-OSO3H: Wang-OSO3H was prepared by adding freshly distilled ClSO3H (2.0 mmol) to Wang resin (1.0 mmol) and DIPEA (5.0 mmol) in DCM (10 volumes) and the resulting solution was stirred at 25–35 °C for 2 h. The reaction mass was filtered and washed with DMF (5 × 10 volumes), DCM (5 × 10 volumes), and isopropanol (5 × 10 volumes) and the Wang catalyst was dried at 130 °C for 3 h.
  • (a) Widdecke, H.; Hogde, S. P. (Eds.); Synthesis and Separations Using Functional Polymers; Wiley: New York, 1998; p. 149; (b) Harland, C. E. Ion Exchange, 2nd ed.; Royal Society of Chemistry: London, 1994; (c) Corma, A. Chem. Rev. 1995, 95, 559; (d) Clark, J. H.; Macqquarrie, D. J. Chem. Soc. Rev. 1996, 25, 310; (e) Harmer, M. A.; Sun, Q. Appl. Catal. A 2001, 221, 45; (f) Chakraborthy, A.; Sharma, M. M. React. Funct. Polym. 1993, 20, 1; (g) Gogoi, P. Synlett 2005, 14, 2263; (h) Meziani, M. J.; Zajac, J.; Jones, D. J.; Partyka, S.; Roziere, J.; Auroux, A. Langmuir 2000, 16, 2262; (i) Brunel, D.; Blanc, A. C.; Galarneau, A.; Fajula, F. Catal. Today, 2002, 73, 139.
  • (a) Olah, G. A. Iyer, P. S.; Suryaprakash, G. K. Synthesis, 1986, 513; (b) Sandmacher, K.; Kunne, H.; Kunz, H. Chem. Eng. Technol. 1998, 21, 6; (c) Harmer, M. A. Sun, Q.; Farneth, W. E. J. Am. Chem. Soc. 1996, 118, 7708; (d) Harmer, M. A. Sun, Q.; Farneth, W. E. Adv. Mater. 1998, 10, 1255; (e) Harmer, M. A.; Sun, Q.; Vega, A. J.; Farneth, W. E.; Heidekum, A.; Hoeldrich, W. F. Green Chem. 2000, 2, 7.
  • Safari, J.; Banitaba, S. H.; Khalili, S. D. J. Mol. Catal. A: Chem. 2011, 335, 46–50.
  • Debache, A.; Ghalem, W.; Boulcina, R.; Belfaitah, A.; Rhouati, S.; Carboni, B. Tetrahedron Lett., 2009, 50, 5248–5250.
  • Antonyraj, C. A.; Kannan, S. Appl. Catal., A 2008, 338, 121–129.
  • Adharvana, C. M.; Syamasundar, K. Catal. Commun. 2005, 6, 624–626.
  • Gupta, R.; Gupta, R.; Paul, S.; Loupy, A. Synthesis 2007, 18, 2835–2838.

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