Three-component, one-pot synthesis of benzo[f]indenoquinoline derivatives catalyzed by poly(4-vinylpyridinium) hydrogen sulfate

Nader Ghaffari Khaligh

引用本文: Nader Ghaffari Khaligh. Three-component, one-pot synthesis of benzo[f]indenoquinoline derivatives catalyzed by poly(4-vinylpyridinium) hydrogen sulfate[J]. 催化学报, 2014, 35(4): 474-480. doi: 10.1016/S1872-2067(12)60752-9 shu
Citation:  Nader Ghaffari Khaligh. Three-component, one-pot synthesis of benzo[f]indenoquinoline derivatives catalyzed by poly(4-vinylpyridinium) hydrogen sulfate[J]. Chinese Journal of Catalysis, 2014, 35(4): 474-480. doi: 10.1016/S1872-2067(12)60752-9 shu

Three-component, one-pot synthesis of benzo[f]indenoquinoline derivatives catalyzed by poly(4-vinylpyridinium) hydrogen sulfate

    通讯作者: Nader Ghaffari Khaligh
摘要: 7-Aryl-8H-benzo[f]indeno[2,1-b]quinoline-8-one derivatives were synthesized by means of a one-pot condensation of 2-naphthylamine, aromatic aldehydes, and indane-1,3-dione in ethanol under refluxing conditions in the presence of poly(4-vinylpyridinium) hydrogen sulfate, a solid acid catalyst. This method has the advantages of high yield, clean reaction, simple methodology, and short reaction time. The catalyst could be recycled and reused four times without significant loss of activity. The structure of the novel compounds was confirmed by IR, 1H NMR, and 13C NMR spectroscopy and elemental analysis.

English

    1. [1] Brock E D, Lewis D M, Yousaf T I, Harper H H. WO 9 951 688. 1999[1] Brock E D, Lewis D M, Yousaf T I, Harper H H. WO 9 951 688. 1999

    2. [2] Beagley P, Blackie M A L, Chibale K, Clarkson C, Meijboom R, Moss J R, Smith P J, Su H. Dalton Trans, 2003: 3046[2] Beagley P, Blackie M A L, Chibale K, Clarkson C, Meijboom R, Moss J R, Smith P J, Su H. Dalton Trans, 2003: 3046

    3. [3] Sawada Y, Kayakiri H, Abe Y, Mizutani T, Inamura N, Asano M, Hatori C, Aramori I, Oku T, Tanaka H. J Med Chem, 2004, 47: 2853[3] Sawada Y, Kayakiri H, Abe Y, Mizutani T, Inamura N, Asano M, Hatori C, Aramori I, Oku T, Tanaka H. J Med Chem, 2004, 47: 2853

    4. [4] Ma Z Z, Hano Y, Nomura T, Chen Y J. Bioorg Med Chem Lett, 2004, 14: 1193[4] Ma Z Z, Hano Y, Nomura T, Chen Y J. Bioorg Med Chem Lett, 2004, 14: 1193

    5. [5] Denton T T, Zhang X D, Cashman J R. J Med Chem, 2005, 48: 224[5] Denton T T, Zhang X D, Cashman J R. J Med Chem, 2005, 48: 224

    6. [6] Fokialakis N, Magiatis P, Chinou L I, Mitaku S, Tillequin F. Chem Pharm Bull, 2002, 50: 413[6] Fokialakis N, Magiatis P, Chinou L I, Mitaku S, Tillequin F. Chem Pharm Bull, 2002, 50: 413

    7. [7] Fossa P, Mosti L, Menozzi G, Marzano C, Baccichetti F, Bordin F. Bioorg Med Chem, 2002, 10: 743[7] Fossa P, Mosti L, Menozzi G, Marzano C, Baccichetti F, Bordin F. Bioorg Med Chem, 2002, 10: 743

    8. [8] Ryckebusch A, Deprez-Poulain R, Maes L, Debreu-Fontaine M A, Mouray E, Grellier P, Sergheraert C. J Med Chem, 2003, 46: 542[8] Ryckebusch A, Deprez-Poulain R, Maes L, Debreu-Fontaine M A, Mouray E, Grellier P, Sergheraert C. J Med Chem, 2003, 46: 542

    9. [9] Morgan L R, Jursic B S, Hooper C L, Neumann D M, Thangaraj K, LeBlanc B. Bioorg Med Chem Lett, 2002, 12: 3407[9] Morgan L R, Jursic B S, Hooper C L, Neumann D M, Thangaraj K, LeBlanc B. Bioorg Med Chem Lett, 2002, 12: 3407

    10. [10] Sakata G, Makino K, Karasawa Y. Heterocycles, 1988, 27: 2481[10] Sakata G, Makino K, Karasawa Y. Heterocycles, 1988, 27: 2481

    11. [11] Demeunynck M, Moucheron C, Mesmaeker A K D. Tetrahedron Lett, 2002, 43: 261[11] Demeunynck M, Moucheron C, Mesmaeker A K D. Tetrahedron Lett, 2002, 43: 261

    12. [12] Baraznenok I L, Nenajdenko V G, Balenkova E S. Eur J Org Chem, 1999: 937[12] Baraznenok I L, Nenajdenko V G, Balenkova E S. Eur J Org Chem, 1999: 937

    13. [13] Ali M M, Tasneem K C, Rajanna K C, Prakash P K S. Synlett, 2001: 251[13] Ali M M, Tasneem K C, Rajanna K C, Prakash P K S. Synlett, 2001: 251

    14. [14] Palacios F, de Retana A M O, Oyarzabal J. Tetrahedron, 1999, 55: 5947[14] Palacios F, de Retana A M O, Oyarzabal J. Tetrahedron, 1999, 55: 5947

    15. [15] Meshram H M, Reddy G S, Reddy M M, Yadav J S. Tetrahedron Lett, 1998, 39: 4103[15] Meshram H M, Reddy G S, Reddy M M, Yadav J S. Tetrahedron Lett, 1998, 39: 4103

    16. [16] Cho C S, Kim B T, Kim T J, Shim S C. Chem Commun, 2001: 2576[16] Cho C S, Kim B T, Kim T J, Shim S C. Chem Commun, 2001: 2576

    17. [17] Crousse B, Begue J P, Bonnet-Delpon D. J Org Chem, 2000, 65: 5009[17] Crousse B, Begue J P, Bonnet-Delpon D. J Org Chem, 2000, 65: 5009

    18. [18] Lin X F, Cui S L, Wang Y G. Tetrahedron Lett, 2006, 47: 4509[18] Lin X F, Cui S L, Wang Y G. Tetrahedron Lett, 2006, 47: 4509

    19. [19] Lin XF, Cui SL, Wang YG. Tetrahedron Lett, 2006, 47: 3127[19] Lin XF, Cui SL, Wang YG. Tetrahedron Lett, 2006, 47: 3127

    20. [20] Skraup H. Chem Ber, 1880, 13: 2086[20] Skraup H. Chem Ber, 1880, 13: 2086

    21. [21] Manske R H F, Kulka M. Org React, 1953, 7: 59[21] Manske R H F, Kulka M. Org React, 1953, 7: 59

    22. [22] Doebner O, Miller V W. Chem Ber, 1881, 14: 2812[22] Doebner O, Miller V W. Chem Ber, 1881, 14: 2812

    23. [23] Conrad M, Limbach L. Chem Ber, 1887, 20: 944[23] Conrad M, Limbach L. Chem Ber, 1887, 20: 944

    24. [24] Combes A. Compt Rend, 1888, 106: 142[24] Combes A. Compt Rend, 1888, 106: 142

    25. [25] Pfitzinger W. J Prakt Chem, 1886, 33: 100[25] Pfitzinger W. J Prakt Chem, 1886, 33: 100

    26. [26] Povarov L S. Russ Chem Rev, 1967, 36: 656[26] Povarov L S. Russ Chem Rev, 1967, 36: 656

    27. [27] Kouznetsov V V. Tetrahedron, 2009, 65: 2721[27] Kouznetsov V V. Tetrahedron, 2009, 65: 2721

    28. [28] Haghighi M G, Rashidi M, Nabavizadeh S M, Jamali S, Puddephatt R J. Dalton Trans, 2010, 39: 11396[28] Haghighi M G, Rashidi M, Nabavizadeh S M, Jamali S, Puddephatt R J. Dalton Trans, 2010, 39: 11396

    29. [29] Baratta W, Fanfoni L, Magnolia S, Siega K, Rigo P. Eur J Inorg Chem, 2010: 1419[29] Baratta W, Fanfoni L, Magnolia S, Siega K, Rigo P. Eur J Inorg Chem, 2010: 1419

    30. [30] Baratta W, Ballico M, Baldino S, Chelucci G, Herdtweck E, Siega K, Magnolia S, Rigo P. Chem Eur J, 2008, 14: 9148[30] Baratta W, Ballico M, Baldino S, Chelucci G, Herdtweck E, Siega K, Magnolia S, Rigo P. Chem Eur J, 2008, 14: 9148

    31. [31] Prema D, Wiznycia A V, Scott B M T, Hilborn J, Desper J, Levy C J. Dalton Trans, 2007: 4788[31] Prema D, Wiznycia A V, Scott B M T, Hilborn J, Desper J, Levy C J. Dalton Trans, 2007: 4788

    32. [32] Atatreh N, Stojkoski C, Smith P, Booker G W, Dive C, Frenkel A D, Freeman S, Bryce R A. Bioorg Med Chem Lett, 2008, 18: 1217[32] Atatreh N, Stojkoski C, Smith P, Booker G W, Dive C, Frenkel A D, Freeman S, Bryce R A. Bioorg Med Chem Lett, 2008, 18: 1217

    33. [33] Cappelli A, Giuliani G, Gallelli A, Valenti S, Anzini M, Mennuni L, Makovec F, Cupello A, Vomero S. Bioorg Med Chem, 2005, 13: 3455[33] Cappelli A, Giuliani G, Gallelli A, Valenti S, Anzini M, Mennuni L, Makovec F, Cupello A, Vomero S. Bioorg Med Chem, 2005, 13: 3455

    34. [34] Murthy M, Pedemonte N, MacVinish L, Malietta L, Cuthbert A. Eur J Pharmacol, 2005, 516: 118[34] Murthy M, Pedemonte N, MacVinish L, Malietta L, Cuthbert A. Eur J Pharmacol, 2005, 516: 118

    35. [35] Szkotak AJ, Murthy M, MacVinish L J, Duszyk M, Cuthbert A W. Br J Pharmacol, 2004, 142: 531[35] Szkotak AJ, Murthy M, MacVinish L J, Duszyk M, Cuthbert A W. Br J Pharmacol, 2004, 142: 531

    36. [36] Kerry M A, Boyd G W, Mackay S P, Meth-Cohn O, Platt L. J Chem Soc, Perkin Trans 1, 1999: 2315[36] Kerry M A, Boyd G W, Mackay S P, Meth-Cohn O, Platt L. J Chem Soc, Perkin Trans 1, 1999: 2315

    37. [37] Cappelli A, Anzini M, Vomero S, Mennuni L, Makovec F, Doucet E, Hamon M, Bruni G, Romeo M R, Menziani M C, De Benedetti P G, Langer T. J Med Chem, 1998, 41: 728[37] Cappelli A, Anzini M, Vomero S, Mennuni L, Makovec F, Doucet E, Hamon M, Bruni G, Romeo M R, Menziani M C, De Benedetti P G, Langer T. J Med Chem, 1998, 41: 728

    38. [38] Tsai A S, Tauchert M E, Bergman R G, Ellman JA. J Am Chem Soc, 2011, 133: 1248[38] Tsai A S, Tauchert M E, Bergman R G, Ellman JA. J Am Chem Soc, 2011, 133: 1248

    39. [39] Kakiuchi F, Kochi T, Mutsutani H, Kobayashi N, Urano S, Sato M, Nishiyama S, Tanabe T. J Am Chem Soc, 2009, 131: 11310[39] Kakiuchi F, Kochi T, Mutsutani H, Kobayashi N, Urano S, Sato M, Nishiyama S, Tanabe T. J Am Chem Soc, 2009, 131: 11310

    40. [40] Yu W Y, Sit W N, Lai K M, Zhou Z Y, Chan A S C. J Am Chem Soc, 2008, 130: 3304[40] Yu W Y, Sit W N, Lai K M, Zhou Z Y, Chan A S C. J Am Chem Soc, 2008, 130: 3304

    41. [41] Dick A R, Hull K L, Sanford M S. J Am Chem Soc, 2004, 126: 2300[41] Dick A R, Hull K L, Sanford M S. J Am Chem Soc, 2004, 126: 2300

    42. [42] Paritala H, Firestine S M. Bioorg Med Chem Lett, 2009, 19: 1584[42] Paritala H, Firestine S M. Bioorg Med Chem Lett, 2009, 19: 1584

    43. [43] Patel D R, Patel K C. Fiber Polym, 2011, 12: 741[43] Patel D R, Patel K C. Fiber Polym, 2011, 12: 741

    44. [44] Parekh N M, Maheria K C. Arch Appl Sci Res, 2011, 3: 359[44] Parekh N M, Maheria K C. Arch Appl Sci Res, 2011, 3: 359

    45. [45] Sener I, Karci F, Ertan N, Kilic E. Dyes Pigm, 2006, 70: 143[45] Sener I, Karci F, Ertan N, Kilic E. Dyes Pigm, 2006, 70: 143

    46. [46] Karci F, Sener N, Yamac M, Sener I, Demircali A. Dyes Pigm, 2009, 80: 47[46] Karci F, Sener N, Yamac M, Sener I, Demircali A. Dyes Pigm, 2009, 80: 47

    47. [47] Aramoto H, Obora Y, Ishii Y. J Org Chem, 2009, 74: 628[47] Aramoto H, Obora Y, Ishii Y. J Org Chem, 2009, 74: 628

    48. [48] Wang X S, Li Q, Yao C S, Tu S J. Eur J Org Chem, 2008: 3513[48] Wang X S, Li Q, Yao C S, Tu S J. Eur J Org Chem, 2008: 3513

    49. [49] Kozlov N G, Gusak K N. Russ J Org Chem, 2008, 44: 1049[49] Kozlov N G, Gusak K N. Russ J Org Chem, 2008, 44: 1049

    50. [50] Hewlins M J E, Salter R. Synthesis, 2007: 2157[50] Hewlins M J E, Salter R. Synthesis, 2007: 2157

    51. [51] Li A H, Ahmed E, Chen X, Cox M, Crew A P, Dong H Q, Jin M Z, Ma L F, Panicker B, Siu K W, Steinig A G, Stolz K M, Tavares P A R, Volk B, Weng Q H, Werner D, Mulvihill M J. Org Biomol Chem, 2007, 5: 61[51] Li A H, Ahmed E, Chen X, Cox M, Crew A P, Dong H Q, Jin M Z, Ma L F, Panicker B, Siu K W, Steinig A G, Stolz K M, Tavares P A R, Volk B, Weng Q H, Werner D, Mulvihill M J. Org Biomol Chem, 2007, 5: 61

    52. [52] Alajarin M, Vidal A, Ortin M M. Tetrahedron, 2005, 61: 7613[52] Alajarin M, Vidal A, Ortin M M. Tetrahedron, 2005, 61: 7613

    53. [53] Sangu K, Fuchibe K, Akiyama T. Org Lett, 2004, 6: 353[53] Sangu K, Fuchibe K, Akiyama T. Org Lett, 2004, 6: 353

    54. [54] Mahata P K, Venkatesh C, Kumar U K S, Ila H, Junjappa H. J Org Chem, 2003, 68: 3966[54] Mahata P K, Venkatesh C, Kumar U K S, Ila H, Junjappa H. J Org Chem, 2003, 68: 3966

    55. [55] Seeman P, Guan H C, Nobrega J, Jiwa D, Markstein R, Balk J H, Picetti R, Borrelli E van, Tol H H M. Synapse, 1997, 25: 137[55] Seeman P, Guan H C, Nobrega J, Jiwa D, Markstein R, Balk J H, Picetti R, Borrelli E van, Tol H H M. Synapse, 1997, 25: 137

    56. [56] Elslager E F, Short F W, Tendick H F. J Heterocycl. Chem, 1968, 5: 599[56] Elslager E F, Short F W, Tendick H F. J Heterocycl. Chem, 1968, 5: 599

    57. [57] Bierer D E, Dubenko L G, Zhang P S, Lu Q, Imbach P A, Garofalo A W, Phuan P W, Fort D M, Litvak J, Gerber R E, Sloan B, Luo J, Cooper R, Reaven G M. J Med Chem, 1998, 41: 2754[57] Bierer D E, Dubenko L G, Zhang P S, Lu Q, Imbach P A, Garofalo A W, Phuan P W, Fort D M, Litvak J, Gerber R E, Sloan B, Luo J, Cooper R, Reaven G M. J Med Chem, 1998, 41: 2754

    58. [58] Brooks J R, Berman D, Glitzer M S, Gordon L R, Primka R L, Reynolds G F, Rasmusson G H. Prostate, 1982, 3: 35[58] Brooks J R, Berman D, Glitzer M S, Gordon L R, Primka R L, Reynolds G F, Rasmusson G H. Prostate, 1982, 3: 35

    59. [59] Babu G, Perumal P T. Tetrahedron Lett, 1998, 39: 3225[59] Babu G, Perumal P T. Tetrahedron Lett, 1998, 39: 3225

    60. [60] Yadav J S, Reddy B V S, Srinivas R, Madhuri Ch, Ramaligam T. Synlett, 2001: 240[60] Yadav J S, Reddy B V S, Srinivas R, Madhuri Ch, Ramaligam T. Synlett, 2001: 240

    61. [61] Yamato M, Takeuchi Y, Hashigaki K, Ikeda Y, Chang M R, Takeuchi K, Matsushima M, Tsuruo T, Tashiro T, Tsukagoshi S, Yamashita Y, Nakano H. J Med Chem, 1989, 32: 1295[61] Yamato M, Takeuchi Y, Hashigaki K, Ikeda Y, Chang M R, Takeuchi K, Matsushima M, Tsuruo T, Tashiro T, Tsukagoshi S, Yamashita Y, Nakano H. J Med Chem, 1989, 32: 1295

    62. [62] Lu X L, Petersen J L, Wang K K. Org Lett, 2003, 5: 3277[62] Lu X L, Petersen J L, Wang K K. Org Lett, 2003, 5: 3277

    63. [63] Rampa A, Bisi A, Belluti F, Gobbi S, Valenti P, Andrisano V, Cavrini V, Cavalli A, Recanatini M. Bioorg Med Chem, 2000, 8: 497[63] Rampa A, Bisi A, Belluti F, Gobbi S, Valenti P, Andrisano V, Cavrini V, Cavalli A, Recanatini M. Bioorg Med Chem, 2000, 8: 497

    64. [64] Deady L W, Desneves J, Kaye A J, Finlay G J, Baguley B C, Denny W A. Bioorg Med Chem, 2000, 8: 977[64] Deady L W, Desneves J, Kaye A J, Finlay G J, Baguley B C, Denny W A. Bioorg Med Chem, 2000, 8: 977

    65. [65] Deady L W, Desneves J, Kaye A J, Finlay G J, Baguley B C, Denny W A. Bioorg Med Chem, 2001, 9: 445[65] Deady L W, Desneves J, Kaye A J, Finlay G J, Baguley B C, Denny W A. Bioorg Med Chem, 2001, 9: 445

    66. [66] Bu X Y, Deady L W. Synth Commun, 1999, 29: 4223[66] Bu X Y, Deady L W. Synth Commun, 1999, 29: 4223

    67. [67] Schmittel M, Strittmatter M, Vollmann K, Kiau S. Tetrahedron Lett, 1996, 37: 999[67] Schmittel M, Strittmatter M, Vollmann K, Kiau S. Tetrahedron Lett, 1996, 37: 999

    68. [68] Cho C S, Kim B T, Choi H J, Kim T J, Shim S C. Tetrahedron, 2003, 59: 7997[68] Cho C S, Kim B T, Choi H J, Kim T J, Shim S C. Tetrahedron, 2003, 59: 7997

    69. [69] Sunami T, Nishio K, Kanzawa F, Fukuoka K, Kudoh S, Yoshikawa J, Saijo N. Cancer Chemother Pharmacol, 1999, 43: 394[69] Sunami T, Nishio K, Kanzawa F, Fukuoka K, Kudoh S, Yoshikawa J, Saijo N. Cancer Chemother Pharmacol, 1999, 43: 394

    70. [70] Atwell G J, Rewcastle G W, Baguley B C, Denny W A. J Med Chem, 1987, 30: 664[70] Atwell G J, Rewcastle G W, Baguley B C, Denny W A. J Med Chem, 1987, 30: 664

    71. [71] Spicer J A, Gamage S A, Atwell G J, Finlay G J, Baguley B C, Denny W A. J Med Chem, 1997, 40: 1919[71] Spicer J A, Gamage S A, Atwell G J, Finlay G J, Baguley B C, Denny W A. J Med Chem, 1997, 40: 1919

    72. [72] Kohlhagen G, Paull K D, Cushman M, Nagafuji P, Pommier Y. Mol Pharmacol, 1998, 54: 50[72] Kohlhagen G, Paull K D, Cushman M, Nagafuji P, Pommier Y. Mol Pharmacol, 1998, 54: 50

    73. [73] Antony S, Jayaraman M, Laco G, Kohlhagen G, Kohn K W, Cushman M, Pommier Y. Cancer Res, 2003, 63: 7428[73] Antony S, Jayaraman M, Laco G, Kohlhagen G, Kohn K W, Cushman M, Pommier Y. Cancer Res, 2003, 63: 7428

    74. [74] Claret P A, Osborne A G: In: Jones G Ed. The Chemistry of Heterocyclic Compounds (Vol. 32, Part 2). Quinolines: John Wiley & Sons, 1982. 31[74] Claret P A, Osborne A G: In: Jones G Ed. The Chemistry of Heterocyclic Compounds (Vol. 32, Part 2). Quinolines: John Wiley & Sons, 1982. 31

    75. [75] Sawada Y, Kayakiri H, Abe Y, Imai K, Mizutani T, Inamura N, A sano M, Aramori I, Hatori C, Katayama A, Oku T, Tanaka H. J Med Chem, 2004, 47: 1617[75] Sawada Y, Kayakiri H, Abe Y, Imai K, Mizutani T, Inamura N, A sano M, Aramori I, Hatori C, Katayama A, Oku T, Tanaka H. J Med Chem, 2004, 47: 1617

    76. [76] Groisy-Delcey M, Groisy A, Carrez D, Huel C, Chiaroni A, Ducrot P, Bisagni E, Jin L, Leclercq G. Bioorg Med Chem, 2000, 8: 2629[76] Groisy-Delcey M, Groisy A, Carrez D, Huel C, Chiaroni A, Ducrot P, Bisagni E, Jin L, Leclercq G. Bioorg Med Chem, 2000, 8: 2629

    77. [77] Cheng C H, Chen R M, Huang C W, Yang C C. US 20050025995A1. 2005[77] Cheng C H, Chen R M, Huang C W, Yang C C. US 20050025995A1. 2005

    78. [78] Kim J I, Shin I S, Kim H, Lee J K. J Am Chem Soc, 2005, 127: 1614[78] Kim J I, Shin I S, Kim H, Lee J K. J Am Chem Soc, 2005, 127: 1614

    79. [79] Thompson M E, Ma B W, Djurovich P. US 20050164031A1. 2005[79] Thompson M E, Ma B W, Djurovich P. US 20050164031A1. 2005

    80. [80] Sun Y, Sun J, Yan C G. Beilstein J Org Chem, 2013, 9: 8[80] Sun Y, Sun J, Yan C G. Beilstein J Org Chem, 2013, 9: 8

    81. [81] Agra A K, Jenekhe S A. Macromolecules, 1991, 24: 6806[81] Agra A K, Jenekhe S A. Macromolecules, 1991, 24: 6806

    82. [82] Zhang X J, Shetty A S, Jenekhe S A. Macromolecules, 1999, 32: 7422[82] Zhang X J, Shetty A S, Jenekhe S A. Macromolecules, 1999, 32: 7422

    83. [83] Jenekhe S A, Lu L D, Alam M M. Macromolecules, 2001, 34: 7315[83] Jenekhe S A, Lu L D, Alam M M. Macromolecules, 2001, 34: 7315

    84. [84] Khaligh N G. Tetrahedron Lett, 2012, 53: 1637[84] Khaligh N G. Tetrahedron Lett, 2012, 53: 1637

    85. [85] Mamaghani M, Larghani T H. J Chem Res, 2012, 36: 235[85] Mamaghani M, Larghani T H. J Chem Res, 2012, 36: 235

    86. [86] Wang X S, Zhang M M, Zeng Z S, Shi D Q, Tu S J, Wei X Y, Zong Z M. J Heterocycl Chem, 2006, 43: 989[86] Wang X S, Zhang M M, Zeng Z S, Shi D Q, Tu S J, Wei X Y, Zong Z M. J Heterocycl Chem, 2006, 43: 989

    87. [87] Tu S J, Zhang Y, Zhang J Y, Jiang B, Jia R H, Zhang J P, Ji S J. Synlett, 2006: 2785[87] Tu S J, Zhang Y, Zhang J Y, Jiang B, Jia R H, Zhang J P, Ji S J. Synlett, 2006: 2785

    88. [88] Tu S J, Wu S S, Yan S, Hao W J, Zhang X H, Cao X D, Han Z G, Jiang B, Shi F, Xia M, Zhou J F. J Comb Chem, 2009, 11: 239[88] Tu S J, Wu S S, Yan S, Hao W J, Zhang X H, Cao X D, Han Z G, Jiang B, Shi F, Xia M, Zhou J F. J Comb Chem, 2009, 11: 239

    89. [89] Heravi M M, Hosseini T, Derikvand F, Beheshtiha S Y S, Bamoharram F F. Synth Commun, 2010, 40: 2402[89] Heravi M M, Hosseini T, Derikvand F, Beheshtiha S Y S, Bamoharram F F. Synth Commun, 2010, 40: 2402

    90. [90] Tanabe K, Hölderich W F. Appl Catal A, 1999, 181: 399[90] Tanabe K, Hölderich W F. Appl Catal A, 1999, 181: 399

    91. [91] Ghorbani-Choghamarani A, Zolfigol M A, Hajjami M, Sardari S. Synth Commun, 2013, 43: 52[91] Ghorbani-Choghamarani A, Zolfigol M A, Hajjami M, Sardari S. Synth Commun, 2013, 43: 52

    92. [92] Li M, Chen D Y, Zhu X F. Chin J Catal (催化学报), 2013, 34: 1674[92] Li M, Chen D Y, Zhu X F. Chin J Catal (催化学报), 2013, 34: 1674

    93. [93] Rahi T, Baghernejad M, Niknam K. Chin J Catal (催化学报), 2012, 33: 1095[93] Rahi T, Baghernejad M, Niknam K. Chin J Catal (催化学报), 2012, 33: 1095

    94. [94] Cole-Hamilton D J. Science, 2003, 299: 1702[94] Cole-Hamilton D J. Science, 2003, 299: 1702

    95. [95] Chakrabarti A, Sharma M M. React Polym, 1993, 20: 1[95] Chakrabarti A, Sharma M M. React Polym, 1993, 20: 1

    96. [96] Riego J M, Sedin Z, Zaldivar J M, Marziano N C, Tortato C. Tetrahedron Lett, 1996, 37: 513[96] Riego J M, Sedin Z, Zaldivar J M, Marziano N C, Tortato C. Tetrahedron Lett, 1996, 37: 513

    97. [97] Turro N J. Tetrahedron, 1987, 43: 1589[97] Turro N J. Tetrahedron, 1987, 43: 1589

    98. [98] Zolfigol M A, Chehardoli G, Dehghanian M, Niknam K, Shirini F, Khoramabadi-Zad A. J Chin Chem Soc (Taipei), 2008, 55: 885[98] Zolfigol M A, Chehardoli G, Dehghanian M, Niknam K, Shirini F, Khoramabadi-Zad A. J Chin Chem Soc (Taipei), 2008, 55: 885

    99. [99] Weber U S, Steffen B, Siegers C P. Res Commun Mol Pathol Pharmacol, 1998, 99: 193[99] Weber U S, Steffen B, Siegers C P. Res Commun Mol Pathol Pharmacol, 1998, 99: 193

    100. [100] Li Y O. Petrochem Technol, 1981, 54: 309[100] Li Y O. Petrochem Technol, 1981, 54: 309

    101. [101] Patil A D, Freyer A J, Eggleston D S, Haltiwanger R C, Bean M F, Taylor P B, Caranfa M J, Breen A L, Bartus H R, Johnson R K, Hertzberg R P, Westley J W. J Med Chem, 1993, 36: 4131[101] Patil A D, Freyer A J, Eggleston D S, Haltiwanger R C, Bean M F, Taylor P B, Caranfa M J, Breen A L, Bartus H R, Johnson R K, Hertzberg R P, Westley J W. J Med Chem, 1993, 36: 4131

    102. [102] Khaligh N G, Shirini F. J Mol Catal A, 2011, 348: 20[102] Khaligh N G, Shirini F. J Mol Catal A, 2011, 348: 20

    103. [103] Wang X S, Zhou J, Yang K, Li Y L. Tetrahedron Lett, 2011, 52: 612[103] Wang X S, Zhou J, Yang K, Li Y L. Tetrahedron Lett, 2011, 52: 612

    104. [104] Tapaswi P K, Mukhopadhyay C. Arkivoc, 2011: 276[104] Tapaswi P K, Mukhopadhyay C. Arkivoc, 2011: 276

    105. [105] Bhargava G, Mohan C, Mahajan M P. Tetrahedron, 2008, 64: 3017[105] Bhargava G, Mohan C, Mahajan M P. Tetrahedron, 2008, 64: 3017

    106. [106] Shi D Q, Ni S N, Yang F, Shi J W, Dou G L, Li X Y, Wang X S, Ji S J. J Heterocycl Chem, 2008, 45: 693[106] Shi D Q, Ni S N, Yang F, Shi J W, Dou G L, Li X Y, Wang X S, Ji S J. J Heterocycl Chem, 2008, 45: 693

    107. [107] Shi D Q, Yang F, Ni S N. J Heterocycl Chem, 2009, 46: 469[107] Shi D Q, Yang F, Ni S N. J Heterocycl Chem, 2009, 46: 469

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  • 发布日期:  2014-04-20
  • 收稿日期:  2013-10-18
  • 网络出版日期:  2013-11-14
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