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Condensation of 2-naphtol with arylaldehydes using acetic acid functionalized ionic liquids as highly efficient and reusable catalysts

Ahmad Reza Moosavi-Zare ,  Mohammad Ali Zolfigol ,  Omid Khaledian ,  Vahid Khakyzadeh

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引用本文: Ahmad Reza Moosavi-Zare, Mohammad Ali Zolfigol, Omid Khaledian, Vahid Khakyzadeh. Condensation of 2-naphtol with arylaldehydes using acetic acid functionalized ionic liquids as highly efficient and reusable catalysts[J]. 催化学报, 2014, 35(4): 573-578. doi: 10.1016/S1872-2067(14)60030-9 shu
Citation:  Ahmad Reza Moosavi-Zare, Mohammad Ali Zolfigol, Omid Khaledian, Vahid Khakyzadeh. Condensation of 2-naphtol with arylaldehydes using acetic acid functionalized ionic liquids as highly efficient and reusable catalysts[J]. Chinese Journal of Catalysis, 2014, 35(4): 573-578. doi: 10.1016/S1872-2067(14)60030-9 shu

Condensation of 2-naphtol with arylaldehydes using acetic acid functionalized ionic liquids as highly efficient and reusable catalysts

    通讯作者: Ahmad Reza Moosavi-Zare, Mohammad Ali Zolfigol; Ahmad Reza Moosavi-Zare, Mohammad Ali Zolfigol
摘要: An efficient solvent-free protocol for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes from the condensation of 2-naphthol with arylaldehydes, using acetic acid functionalized imidazolium salts (1-carboxymethyl-3-methylimidazolium bromide ([cmmim]Br) and 1-carboxymethy1-3-methylimidazolium tetrafluoroborate ([cmmim]BF4) as reusable catalysts, has been developed. The turn over frequency on the catalysts is several times higher than the other previously reported catalysts. Also, thermal gravimetric analysis and powder X-ray diffraction pattern of the catalysts have been studied.

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    1. [1] Wasserscheid P, Keim W. Angew Chem Int Ed, 2000, 39: 3772[1] Wasserscheid P, Keim W. Angew Chem Int Ed, 2000, 39: 3772

    2. [2] Parvulescu V I, Hardacre C. Chem Rev, 2007, 107: 2615[2] Parvulescu V I, Hardacre C. Chem Rev, 2007, 107: 2615

    3. [3] Earle M J, Katdare S P, Seddon K R. Org Lett, 2004, 6: 707[3] Earle M J, Katdare S P, Seddon K R. Org Lett, 2004, 6: 707

    4. [4] Ranu B C, Banerjee S. J Org Chem, 2005, 70: 4517[4] Ranu B C, Banerjee S. J Org Chem, 2005, 70: 4517

    5. [5] Ranu B C, Adak L, Banerjee S. Can J Chem, 2007, 85: 366[5] Ranu B C, Adak L, Banerjee S. Can J Chem, 2007, 85: 366

    6. [6] Pegot B, Vo-Thanh G, Gori D, Loupy A. Tetrahedron Lett, 2004, 45: 6425[6] Pegot B, Vo-Thanh G, Gori D, Loupy A. Tetrahedron Lett, 2004, 45: 6425

    7. [7] Zare A, Moosavi-Zare A R, Hasaninejad A, Parhami A, Khalafi-Nezhad A, Beyzavi M H. Synth Commun, 2009, 39: 3156[7] Zare A, Moosavi-Zare A R, Hasaninejad A, Parhami A, Khalafi-Nezhad A, Beyzavi M H. Synth Commun, 2009, 39: 3156

    8. [8] Zare A, Parhami A, Moosavi-Zare A R, Hasaninejad A, Khalafi-Nezhad A, Beyzavi M H, Can J Chem, 2009, 87: 416[8] Zare A, Parhami A, Moosavi-Zare A R, Hasaninejad A, Khalafi-Nezhad A, Beyzavi M H, Can J Chem, 2009, 87: 416

    9. [9] Hasaninejad A, Zare A, Shekouhy M, Ameri Rad J. J Comb Chem, 2010, 12: 844[9] Hasaninejad A, Zare A, Shekouhy M, Ameri Rad J. J Comb Chem, 2010, 12: 844

    10. [10] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. Org Prep Proced Int, 2010, 42: 95[10] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. Org Prep Proced Int, 2010, 42: 95

    11. [11] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. J Iran Chem Soc, 2010, 7: 646[11] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. J Iran Chem Soc, 2010, 7: 646

    12. [12] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A. Sci Iran, Trans C, 2010, 17: 31[12] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A. Sci Iran, Trans C, 2010, 17: 31

    13. [13] 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[13] 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

    14. [14] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A, Khakyzadeh V. Appl Catal A, 2011, 400: 70[14] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A, Khakyzadeh V. Appl Catal A, 2011, 400: 70

    15. [15] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A, Ghaemi E, Khakyzadeh V, Asgari Zh, Hasaninejad A. Sci Iran, Trans C, 2011, 18: 1365[15] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A, Ghaemi E, Khakyzadeh V, Asgari Zh, Hasaninejad A. Sci Iran, Trans C, 2011, 18: 1365

    16. [16] Zolfigol M A, Khakyzadeh V, Moosavi-Zare A R, Zare A, Azimi S B, Asgari Z, Hasaninejad A. C R Chim, 2012, 15: 719[16] Zolfigol M A, Khakyzadeh V, Moosavi-Zare A R, Zare A, Azimi S B, Asgari Z, Hasaninejad A. C R Chim, 2012, 15: 719

    17. [17] Zare A, Yousofi T, Moosavi-Zare A R. RSC Adv, 2012, 2: 7988[17] Zare A, Yousofi T, Moosavi-Zare A R. RSC Adv, 2012, 2: 7988

    18. [18] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Asgari Z, Shekouhy M, Zare A, Hasaninejad A. RSC Adv, 2012, 2: 8010[18] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Asgari Z, Shekouhy M, Zare A, Hasaninejad A. RSC Adv, 2012, 2: 8010

    19. [19] Zolfigol M A, Khakyzadeh V, Moosavi-Zare A R, Chehardoli G, Derakhshan-Panah F, Zare A, Khaledian O. Sci Iran Trans C, 2012, 19: 1584[19] Zolfigol M A, Khakyzadeh V, Moosavi-Zare A R, Chehardoli G, Derakhshan-Panah F, Zare A, Khaledian O. Sci Iran Trans C, 2012, 19: 1584

    20. [20] 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[20] 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

    21. [21] Zare A, Hekmat-Zadeh T, Mirzaei-Monfared S, Merajoddin M, Torabi-Monfared H, Zolfigol M A, Moosavi-Zare A R, Rostami E, Mokhlesi M, Derakhshan-Panah F, Porbahi S, Balandeh S. S Afr J Chem, 2012, 65: 63[21] Zare A, Hekmat-Zadeh T, Mirzaei-Monfared S, Merajoddin M, Torabi-Monfared H, Zolfigol M A, Moosavi-Zare A R, Rostami E, Mokhlesi M, Derakhshan-Panah F, Porbahi S, Balandeh S. S Afr J Chem, 2012, 65: 63

    22. [22] Zare A, Abi F, Moosavi-Zare A R, Beyzavi M H, Zolfigol M A. J Mol Liq, 2013, 178: 113[22] Zare A, Abi F, Moosavi-Zare A R, Beyzavi M H, Zolfigol M A. J Mol Liq, 2013, 178: 113

    23. [23] Moosavi-Zare A R, Zolfigol M A, Zarei M, Zare A, Khakyzadeh V. J Mol Liq, 2013, 186: 63[23] Moosavi-Zare A R, Zolfigol M A, Zarei M, Zare A, Khakyzadeh V. J Mol Liq, 2013, 186: 63

    24. [24] Khazaei A, Zolfigol M A. Moosavi-Zare A R, Afsar J, Zare A, Khakyzadeh V, Beyzavi M H. Chin J Catal (催化学报), 2013, 34: 1936[24] Khazaei A, Zolfigol M A. Moosavi-Zare A R, Afsar J, Zare A, Khakyzadeh V, Beyzavi M H. Chin J Catal (催化学报), 2013, 34: 1936

    25. [25] Moosavi-Zare A R, Zolfigol M A, Zarei M, Zare A, Khakyzadeh V, Hasaninejad A. Appl Catal A, 2013, 467: 61[25] Moosavi-Zare A R, Zolfigol M A, Zarei M, Zare A, Khakyzadeh V, Hasaninejad A. Appl Catal A, 2013, 467: 61

    26. [26] Hideo T. JP Patent 56005480. 1981[26] Hideo T. JP Patent 56005480. 1981

    27. [27] Lambert R W, Martin J A, Merrett J H, Parkes K E B, Thomas G J. WO Patent 9706178. 1997[27] Lambert R W, Martin J A, Merrett J H, Parkes K E B, Thomas G J. WO Patent 9706178. 1997

    28. [28] Poupelin J P, Saint-Ruf G, Foussard-Blanpin O, Narcisse G, Uchida-Ernouf G, Lacroix R, Europ J Med Chem, 1978, 13: 67[28] Poupelin J P, Saint-Ruf G, Foussard-Blanpin O, Narcisse G, Uchida-Ernouf G, Lacroix R, Europ J Med Chem, 1978, 13: 67

    29. [29] Ion R M, Planner A, Wiktorowicz K, Frackowiak D. Acta Biochim Pol, 1998, 45: 833[29] Ion R M, Planner A, Wiktorowicz K, Frackowiak D. Acta Biochim Pol, 1998, 45: 833

    30. [30] Menchen S M, Benson S C, Lam J Y L, Zhen W G, Sun D Q, Rosenblum B B, Khan S H, Taing M. US Patent 6583168. 2003[30] Menchen S M, Benson S C, Lam J Y L, Zhen W G, Sun D Q, Rosenblum B B, Khan S H, Taing M. US Patent 6583168. 2003

    31. [31] Bekaert A, Andrieux J, Plat M. Tetrahedron Lett, 1992, 33: 2805[31] Bekaert A, Andrieux J, Plat M. Tetrahedron Lett, 1992, 33: 2805

    32. [32] Alcantara-Licudine J P, Kawate M K, Li Q X. J Agric Food Chem, 1997, 45: 766[32] Alcantara-Licudine J P, Kawate M K, Li Q X. J Agric Food Chem, 1997, 45: 766

    33. [33] Pasha M A, Jayashankara V P. Bioorg Med Chem Lett, 2007, 17: 621[33] Pasha M A, Jayashankara V P. Bioorg Med Chem Lett, 2007, 17: 621

    34. [34] Rajitha B, Kumar B S, Reddy Y T, Reddy P N, Sreenivasulu N. Tetrahedron Lett, 2005, 46: 8691[34] Rajitha B, Kumar B S, Reddy Y T, Reddy P N, Sreenivasulu N. Tetrahedron Lett, 2005, 46: 8691

    35. [35] Hong M, Cai C. J Fluorine Chem, 2009, 130: 989[35] Hong M, Cai C. J Fluorine Chem, 2009, 130: 989

    36. [36] Sarma R J, Baruah J B. Dyes Pigments, 2005, 64: 91[36] Sarma R J, Baruah J B. Dyes Pigments, 2005, 64: 91

    37. [37] Khosropour A R, Khodaei M M, Moghannian H. Synlett, 2005: 955[37] Khosropour A R, Khodaei M M, Moghannian H. Synlett, 2005: 955

    38. [38] Bhattacharya A K, Rana K C, Mujahid M, Sehar I, Saxena A K. Bioorg Med Chem Lett, 2009, 19: 5590[38] Bhattacharya A K, Rana K C, Mujahid M, Sehar I, Saxena A K. Bioorg Med Chem Lett, 2009, 19: 5590

    39. [39] Shakibaei G I, Mirzaei P, Bazgir A. Appl Catal A, 2007, 325: 188[39] Shakibaei G I, Mirzaei P, Bazgir A. Appl Catal A, 2007, 325: 188

    40. [40] Mahdavinia G H, Rostamizadeh S, Amani A M, Emdadi Z. Ultrason Sonochem, 2009, 16: 7[40] Mahdavinia G H, Rostamizadeh S, Amani A M, Emdadi Z. Ultrason Sonochem, 2009, 16: 7

    41. [41] Das B, Ravikanth B, Ramu R, Laxminarayana K, Rao B V. J Mol Catal A, 2006, 255: 74[41] Das B, Ravikanth B, Ramu R, Laxminarayana K, Rao B V. J Mol Catal A, 2006, 255: 74

    42. [42] Bigdeli M A, Heravi M M, Mahdavinia G H. J Mol Catal A, 2007, 275: 25[42] Bigdeli M A, Heravi M M, Mahdavinia G H. J Mol Catal A, 2007, 275: 25

    43. [43] Amini M M, Seyyedhamzeh M, Bazgir A. Appl Catal A, 2007, 323: 242[43] Amini M M, Seyyedhamzeh M, Bazgir A. Appl Catal A, 2007, 323: 242

    44. [44] Bigdeli M A, Heravi M M, Mahdavinia G H. Catal Commun, 2007, 8: 1595[44] Bigdeli M A, Heravi M M, Mahdavinia G H. Catal Commun, 2007, 8: 1595

    45. [45] Su W K, Yang D, Jin C, Zhang B. Tetrahedron Lett, 2008, 49: 3391[45] Su W K, Yang D, Jin C, Zhang B. Tetrahedron Lett, 2008, 49: 3391

    46. [46] Makaev F, Styngach E, Shargarovskii V, Bets L, Vlad L, Barba A. Russ J Org Chem, 2010, 46: 610[46] Makaev F, Styngach E, Shargarovskii V, Bets L, Vlad L, Barba A. Russ J Org Chem, 2010, 46: 610

    47. [47] Fei Z F, Zhao D B, Geldbach T J, Scopelliti R, Dyson P J. Chem Eur J, 2004, 10: 4886[47] Fei Z F, Zhao D B, Geldbach T J, Scopelliti R, Dyson P J. Chem Eur J, 2004, 10: 4886

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  • 发布日期:  2014-04-20
  • 收稿日期:  2013-12-03
  • 网络出版日期:  2014-01-13
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