Synthesis of hexahydroquinolines using the new ionic liquid sulfonic acid functionalized pyridinium chloride as a catalyst

Cuihua Xuebao/Chinese Journal of Catalysis

Volumn 34, Issue 10, 2013, Pages 1936-1944

  Khazaei, Ardeshir ^a   Zolfigol, Mohammad Ali ^a   Moosavi Zare, Ahmad Reza ^b   Afsar, Javad ^a   Zare, Abdolkarim ^c   Khakyzadeh, Vahid ^a   Beyzavi, Mohammad Hassan ^d  

^a BU ALI SINA UNIVERSITY   (Iran)

^b University of Sayyed Jamaleddin Asadabadi   (Iran)

^c PAYAME NOOR UNIVERSITY   (Iran)

^d FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Br nsted acidic ionic liquid; Hexahydroquinoline; Solvent free synthesis

Indexed keywords

ACIDIC IONIC LIQUIDS; DERIVATIVE THERMOGRAVIMETRY; HEXAHYDROQUINOLINE; MULTICOMPONENT CONDENSATION; PYRIDINIUM; SOLVENT FREE CONDITIONS; SOLVENT FREE SYNTHESIS; SULFONIC ACID-FUNCTIONALIZED;

CATALYSTS; CHLORINE COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PYRIDINE; SYNTHESIS (CHEMICAL); THERMOGRAVIMETRIC ANALYSIS;

IONIC LIQUIDS;

EID: 84886669977     PISSN: 02539837     EISSN: None     Source Type: Journal    
DOI: 10.1016/s1872-2067(12)60678-0     Document Type: Article

References (49)

1. Pavlinac J, Zupan M, Laali K K, Stavber S. Tetrahedron, 2009, 65: 5625
2. Olivier-Bourbigou H, Magna L, Morvan D. Appl Catal A, 2010, 373: 1
3. Hapiot P, Lagrost C. Chem Rev, 2008, 108: 2238
4. Wasserscheid P, Welton T. Ionic Liquids in Synthesis. Weinheim: Wiley-VCH, 2008
5. Hasaninejad A, Zare A, Shekouhy M, Ameri Rad J. J Comb Chem, 2010, 12: 844
6. Zare A, Parhami A, Moosavi-Zare A R, Hasaninejad A, Khalafi-Nezhad A, Beyzavi M H. Can J Chem, 2009, 87: 416
7. Eichmann M, Keim W, Haumann M, Melcher B U, Wasserscheid P. J Mol Catal A, 2009, 314: 42
8. Kim Y J, Varma R S. Tetrahedron Lett, 2005, 46: 1467
9. Öchsner E, Schneider M J, Meyer C, Haumann M, Wasserscheid P. Appl Catal A, 2011, 399: 35
10. Zare A, Abi F, Moosavi-Zare A R, Beyzavi M H, Zolfigol M A. J Mol Liq, 2013, 178: 113
11. Shaterian H R, Ranjbar M. J Mol Liq, 2011, 160: 40
12. Zolfigol M A, Khakyzadeh V, Moosavi-Zare A R, Zare A, Azimi S B, Asgari Z, Hasaninejad A. C R Chim, 2012, 15: 719
13. Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. J Iran Chem Soc, 2010, 7: 646
14. Shaterian H R, Ranjbar M, Azizi K. J Mol Liq, 2011, 162: 95
15. Zare A, Moosavi-Zare A R, Merajoddin M, Zolfigol M A, Hekmat-Zadeh T, Hasaninejad A, Khazaei A, Mokhlesi M, Khakyzadeh V, Derakhshan-Panah F, Beyzavi M H, Rostami E, Arghoon A, Roohandeh R. J Mol Liq, 2012, 167: 69
16. Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A, Khakyzadeh V. Appl Catal A, 2011, 400: 70
17. Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. Org Prep Proced Int, 2010, 42: 95
18. Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A, Kruger H G, Asgari Z, Khakyzadeh V, Kazem-Rostami M. J Org Chem,2012, 77: 3640
19. Zhu J, Bienayme H. Multicomponent Reactions. Weinheim: Wiley, 2005
20. Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A, Khojasteh M, Asgari Z, Khakyzadeh V, Khalafi-Nezhad A. Catal Commun, 2012, 20: 54
21. Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A, Parhami A, Khalafi-Nezhad A. Appl Catal A, 2010, 386: 179
22. Glass B D, Brown M E, Drummond P M. In: Albini A, Fasani E eds. Drugs: Photochemistry and Photostability. Cambridge: The Royal Society of Chemistry, 1998. 134
23. Beijersbergen van Henegouwen G M J. In: Testa B, Meyer U A eds. Advances in Drug Research. Vol 29. London: Academic Press, 1997. 79
24. Görlitzer K, Baltrusch H J, Gossnitzer E, Wendelin W. Pharmazie, 2000, 55: 35
25. De Vries H, Beijersbergen van Henegouwen G M J. Photochem Photobiol, 1995, 62: 959
26. Eisner U, Kuthan J. Chem Rev, 1972, 72: 1
27. Stout D M, Meyers A I. Chem Rev, 1982, 82: 223
28. Chorvat R J, Rorig K J. J Org Chem, 1988, 53: 5779
29. Kappe C O, Fabian W M F, Semones M A. Tetrahedron, 1997, 53: 2803
30. Kappe C O. Tetrahedron, 1993, 49: 6937
31. Safak C, Sahin I, Sunal R. Arzneimittel Forsch, 1990, 40: 119
32. Simsek R, Ismailoglu U B, Safak C, Sahin-Erdemli I. Farmaco, 2000, 55: 665
33. Larsen R D, Corley E G, King A O, Carrol J D, Davis P, Verhoeven T R, Reider P J, Labelle M, Gauthier J Y, Xiang Y B, Zamboni R J. J Org Chem, 1996, 61: 3398
34. Chen Y L, Fang K C, Sheu J Y, Hsu S L, Tzeng C C. J Med Chem, 2001, 44: 2374
35. Roma G, Di Braccio M, Grossi G, Mattioli F, Chia M. Eur J Med Chem, 2000, 35: 1021
36. Geng X, Li S S, Bian X Q, Xie Z Y, Wang C D. ARKIVOC, 2008: 50
37. Maguire M P, Sheets K R, McVety K, Spada A P, Zilberstein A. J Med Chem, 1994, 37: 2129
38. Billker O, Lindo V, Panico M, Etienne A E, Paxton T, Dell A, Rogers M, Sinden R E, Morris H R. Nature, 1998, 392: 289
39. Song S J, Shan Z X, Jin Y. Synth Commun, 2010, 40: 3067
40. Zhang X L, Sheng S R, Liu X L, Liu X L. ARKIVOC, 2007: 79
41. Kumar A, Maurya R A. Tetrahedron, 2007, 63: 1946
42. Wang L M, Sheng J, Zhang L, Han J W, Fan Z Y, Tian H, Qian C T. Tetrahedron, 2005, 61: 1539
43. Ziarani G M, Badiei A R, Khaniania Y, Haddadpour M. Iran J Chem Chem Eng, 2010, 29: 1
44. Pasunooti K K, Jensen C N, Chai H, Leow M L, Zhang D W, Liu X W. J Comb Chem, 2010, 12: 577
45. Surasani R, Kalita D, Rao A V D, Yarbagi K, Chandrasekhar K B. J Fluorine Chem, 2012, 135: 91
46. Hong M, Cai C, Yi W B. J Fluorine Chem, 2010, 131: 111
47. Saha M, Pal A K. Tetrahedron Lett, 2011, 52: 4872
48. Ajinomoto Co Inc. JP Patent 59 134 751 A. 1984
49. Sakota N, Nomura S, Ito S. JP Patent 03 024 039 A. 1991