全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用：99美元
投递稿件

查看量下载量

相关文章

更多...
催化学报  2014 

Three-component,one-potsynthesisofbenzo[f]indenoquinolinederivativescatalyzedbypoly(4-vinylpyridinium)hydrogensulfate

DOI: 10.1016/S1872-2067(12)60752-9, PP. 474-480

Keywords: Benzoquinoline,Hetereogeneouscatalyst,2-Naphthylamine,Indane-1,3-dione,Three-componentreaction,One-potcondensation

Full-Text   Cite this paper   Add to My Lib

Abstract:

？7-Aryl-8H-benzo[f]indeno[2,1-b]quinoline-8-onederivativesweresynthesizedbymeansofaone-potcondensationof2-naphthylamine,aromaticaldehydes,andindane-1,3-dioneinethanolunderrefluxingconditionsinthepresenceofpoly(4-vinylpyridinium)hydrogensulfate,asolidacidcatalyst.Thismethodhastheadvantagesofhighyield,cleanreaction,simplemethodology,andshortreactiontime.Thecatalystcouldberecycledandreusedfourtimeswithoutsignificantlossofactivity.ThestructureofthenovelcompoundswasconfirmedbyIR,1HNMR,and13CNMRspectroscopyandelementalanalysis.

 References

[1]  Thompson M E, Ma B W, Djurovich P. US 20050164031A1. 2005
[2]  Sun Y, Sun J, Yan C G. Beilstein J Org Chem, 2013, 9: 8
[3]  Agra A K, Jenekhe S A. Macromolecules, 1991, 24: 6806
[4]  Zhang X J, Shetty A S, Jenekhe S A. Macromolecules, 1999, 32: 7422
[5]  Khaligh N G. Tetrahedron Lett, 2012, 53: 1637
[6]  Tu S J, Zhang Y, Zhang J Y, Jiang B, Jia R H, Zhang J P, Ji S J. Synlett, 2006: 2785
[7]  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
[8]  Heravi M M, Hosseini T, Derikvand F, Beheshtiha S Y S, Bamoharram F F. Synth Commun, 2010, 40: 2402
[9]  Li M, Chen D Y, Zhu X F. Chin J Catal (催化学报), 2013, 34: 1674
[10]  Rahi T, Baghernejad M, Niknam K. Chin J Catal (催化学报), 2012, 33: 1095
[11]  Cole-Hamilton D J. Science, 2003, 299: 1702
[12]  Chakrabarti A, Sharma M M. React Polym, 1993, 20: 1
[13]  Riego J M, Sedin Z, Zaldivar J M, Marziano N C, Tortato C. Tetrahedron Lett, 1996, 37: 513
[14]  Turro N J. Tetrahedron, 1987, 43: 1589
[15]  Li Y O. Petrochem Technol, 1981, 54: 309
[16]  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
[17]  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
[18]  Shi D Q, Yang F, Ni S N. J Heterocycl Chem, 2009, 46: 469
[19]  Beagley P, Blackie M A L, Chibale K, Clarkson C, Meijboom R, Moss J R, Smith P J, Su H. Dalton Trans, 2003: 3046
[20]  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
[21]  Ma Z Z, Hano Y, Nomura T, Chen Y J. Bioorg Med Chem Lett, 2004, 14: 1193
[22]  Ryckebusch A, Deprez-Poulain R, Maes L, Debreu-Fontaine M A, Mouray E, Grellier P, Sergheraert C. J Med Chem, 2003, 46: 542
[23]  Demeunynck M, Moucheron C, Mesmaeker A K D. Tetrahedron Lett, 2002, 43: 261
[24]  Ali M M, Tasneem K C, Rajanna K C, Prakash P K S. Synlett, 2001: 251
[25]  Palacios F, de Retana A M O, Oyarzabal J. Tetrahedron, 1999, 55: 5947
[26]  Meshram H M, Reddy G S, Reddy M M, Yadav J S. Tetrahedron Lett, 1998, 39: 4103
[27]  Crousse B, Begue J P, Bonnet-Delpon D. J Org Chem, 2000, 65: 5009
[28]  Lin X F, Cui S L, Wang Y G. Tetrahedron Lett, 2006, 47: 4509
[29]  Lin XF, Cui SL, Wang YG. Tetrahedron Lett, 2006, 47: 3127
[30]  Doebner O, Miller V W. Chem Ber, 1881, 14: 2812
[31]  Conrad M, Limbach L. Chem Ber, 1887, 20: 944
[32]  Pfitzinger W. J Prakt Chem, 1886, 33: 100
[33]  Povarov L S. Russ Chem Rev, 1967, 36: 656
[34]  Kouznetsov V V. Tetrahedron, 2009, 65: 2721
[35]  Haghighi M G, Rashidi M, Nabavizadeh S M, Jamali S, Puddephatt R J. Dalton Trans, 2010, 39: 11396
[36]  Baratta W, Fanfoni L, Magnolia S, Siega K, Rigo P. Eur J Inorg Chem, 2010: 1419
[37]  Baratta W, Ballico M, Baldino S, Chelucci G, Herdtweck E, Siega K, Magnolia S, Rigo P. Chem Eur J, 2008, 14: 9148
[38]  Prema D, Wiznycia A V, Scott B M T, Hilborn J, Desper J, Levy C J. Dalton Trans, 2007: 4788
[39]  Aramoto H, Obora Y, Ishii Y. J Org Chem, 2009, 74: 628
[40]  Kozlov N G, Gusak K N. Russ J Org Chem, 2008, 44: 1049
[41]  Alajarin M, Vidal A, Ortin M M. Tetrahedron, 2005, 61: 7613
[42]  Mahata P K, Venkatesh C, Kumar U K S, Ila H, Junjappa H. J Org Chem, 2003, 68: 3966
[43]  Elslager E F, Short F W, Tendick H F. J Heterocycl. Chem, 1968, 5: 599
[44]  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
[45]  Brooks J R, Berman D, Glitzer M S, Gordon L R, Primka R L, Reynolds G F, Rasmusson G H. Prostate, 1982, 3: 35
[46]  Babu G, Perumal P T. Tetrahedron Lett, 1998, 39: 3225
[47]  Bu X Y, Deady L W. Synth Commun, 1999, 29: 4223
[48]  Schmittel M, Strittmatter M, Vollmann K, Kiau S. Tetrahedron Lett, 1996, 37: 999
[49]  Spicer J A, Gamage S A, Atwell G J, Finlay G J, Baguley B C, Denny W A. J Med Chem, 1997, 40: 1919
[50]  Kim J I, Shin I S, Kim H, Lee J K. J Am Chem Soc, 2005, 127: 1614
[51]  Brock E D, Lewis D M, Yousaf T I, Harper H H. WO 9 951 688. 1999
[52]  Denton T T, Zhang X D, Cashman J R. J Med Chem, 2005, 48: 224
[53]  Fokialakis N, Magiatis P, Chinou L I, Mitaku S, Tillequin F. Chem Pharm Bull, 2002, 50: 413
[54]  Fossa P, Mosti L, Menozzi G, Marzano C, Baccichetti F, Bordin F. Bioorg Med Chem, 2002, 10: 743
[55]  Morgan L R, Jursic B S, Hooper C L, Neumann D M, Thangaraj K, LeBlanc B. Bioorg Med Chem Lett, 2002, 12: 3407
[56]  Sakata G, Makino K, Karasawa Y. Heterocycles, 1988, 27: 2481
[57]  Baraznenok I L, Nenajdenko V G, Balenkova E S. Eur J Org Chem, 1999: 937
[58]  Cho C S, Kim B T, Kim T J, Shim S C. Chem Commun, 2001: 2576
[59]  Skraup H. Chem Ber, 1880, 13: 2086
[60]  Manske R H F, Kulka M. Org React, 1953, 7: 59
[61]  Combes A. Compt Rend, 1888, 106: 142
[62]  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
[63]  Cappelli A, Giuliani G, Gallelli A, Valenti S, Anzini M, Mennuni L, Makovec F, Cupello A, Vomero S. Bioorg Med Chem, 2005, 13: 3455
[64]  Murthy M, Pedemonte N, MacVinish L, Malietta L, Cuthbert A. Eur J Pharmacol, 2005, 516: 118
[65]  Szkotak AJ, Murthy M, MacVinish L J, Duszyk M, Cuthbert A W. Br J Pharmacol, 2004, 142: 531
[66]  Kerry M A, Boyd G W, Mackay S P, Meth-Cohn O, Platt L. J Chem Soc, Perkin Trans 1, 1999: 2315
[67]  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
[68]  Tsai A S, Tauchert M E, Bergman R G, Ellman JA. J Am Chem Soc, 2011, 133: 1248
[69]  Kakiuchi F, Kochi T, Mutsutani H, Kobayashi N, Urano S, Sato M, Nishiyama S, Tanabe T. J Am Chem Soc, 2009, 131: 11310
[70]  Yu W Y, Sit W N, Lai K M, Zhou Z Y, Chan A S C. J Am Chem Soc, 2008, 130: 3304
[71]  Dick A R, Hull K L, Sanford M S. J Am Chem Soc, 2004, 126: 2300
[72]  Paritala H, Firestine S M. Bioorg Med Chem Lett, 2009, 19: 1584
[73]  Patel D R, Patel K C. Fiber Polym, 2011, 12: 741
[74]  Parekh N M, Maheria K C. Arch Appl Sci Res, 2011, 3: 359
[75]  Sener I, Karci F, Ertan N, Kilic E. Dyes Pigm, 2006, 70: 143
[76]  Karci F, Sener N, Yamac M, Sener I, Demircali A. Dyes Pigm, 2009, 80: 47
[77]  Wang X S, Li Q, Yao C S, Tu S J. Eur J Org Chem, 2008: 3513
[78]  Hewlins M J E, Salter R. Synthesis, 2007: 2157
[79]  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
[80]  Sangu K, Fuchibe K, Akiyama T. Org Lett, 2004, 6: 353
[81]  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
[82]  Yadav J S, Reddy B V S, Srinivas R, Madhuri Ch, Ramaligam T. Synlett, 2001: 240
[83]  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
[84]  Lu X L, Petersen J L, Wang K K. Org Lett, 2003, 5: 3277
[85]  Rampa A, Bisi A, Belluti F, Gobbi S, Valenti P, Andrisano V, Cavrini V, Cavalli A, Recanatini M. Bioorg Med Chem, 2000, 8: 497
[86]  Deady L W, Desneves J, Kaye A J, Finlay G J, Baguley B C, Denny W A. Bioorg Med Chem, 2000, 8: 977
[87]  Deady L W, Desneves J, Kaye A J, Finlay G J, Baguley B C, Denny W A. Bioorg Med Chem, 2001, 9: 445
[88]  Cho C S, Kim B T, Choi H J, Kim T J, Shim S C. Tetrahedron, 2003, 59: 7997
[89]  Sunami T, Nishio K, Kanzawa F, Fukuoka K, Kudoh S, Yoshikawa J, Saijo N. Cancer Chemother Pharmacol, 1999, 43: 394
[90]  Atwell G J, Rewcastle G W, Baguley B C, Denny W A. J Med Chem, 1987, 30: 664
[91]  Kohlhagen G, Paull K D, Cushman M, Nagafuji P, Pommier Y. Mol Pharmacol, 1998, 54: 50
[92]  Antony S, Jayaraman M, Laco G, Kohlhagen G, Kohn K W, Cushman M, Pommier Y. Cancer Res, 2003, 63: 7428
[93]  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
[94]  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
[95]  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
[96]  Cheng C H, Chen R M, Huang C W, Yang C C. US 20050025995A1. 2005
[97]  Jenekhe S A, Lu L D, Alam M M. Macromolecules, 2001, 34: 7315
[98]  Mamaghani M, Larghani T H. J Chem Res, 2012, 36: 235
[99]  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
[100]  Tanabe K, H？lderich W F. Appl Catal A, 1999, 181: 399
[101]  Ghorbani-Choghamarani A, Zolfigol M A, Hajjami M, Sardari S. Synth Commun, 2013, 43: 52
[102]  Zolfigol M A, Chehardoli G, Dehghanian M, Niknam K, Shirini F, Khoramabadi-Zad A. J Chin Chem Soc (Taipei), 2008, 55: 885
[103]  Weber U S, Steffen B, Siegers C P. Res Commun Mol Pathol Pharmacol, 1998, 99: 193
[104]  Khaligh N G, Shirini F. J Mol Catal A, 2011, 348: 20
[105]  Wang X S, Zhou J, Yang K, Li Y L. Tetrahedron Lett, 2011, 52: 612
[106]  Tapaswi P K, Mukhopadhyay C. Arkivoc, 2011: 276
[107]  Bhargava G, Mohan C, Mahajan M P. Tetrahedron, 2008, 64: 3017

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133