Citation:
Nader Ghaffari Khaligh. One-pot multicomponent synthesis of unsymmetrical polyhydroquinoline derivatives with 1,1’-butylenebispyridinium hydrogen sulfate as an efficient, halogen-free and reusable Brönsted ionic liquid catalyst[J]. Chinese Journal of Catalysis,
;2014, 35(9): 1497-1503.
doi:
10.1016/S1872-2067(14)60087-5
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1,1'-Butylenebispyridinium hydrogen sulfate is an efficient, halogen-free and reusable Brönsted ionic liquid catalyst for the synthesis of ethyl-4-aryl/heteryl-hexahydro-trimehtyl-5- oxoquinoline-3-carboxylates by the one-pot condensation of dimedone, aryl/heteryl aldehydes, ethyl acetoacetate, and ammonium acetate under solvent-free conditions. This method has the advantages of high yield, clean reaction, simple methodology, and short reaction time. The ionic liquid can be recycled five times without significant loss of the catalytic activity.
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[1]
[1] Parvulescu V I, Hardacre C. Chem Rev, 2007, 107: 2615
-
[2]
[2] Rogers R D, Seddon K R. Ionic Liquids: Industrial Applications to Green Chemistry. American Chemical Society, Washington DC, 2002
-
[3]
[3] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. J Iran Chem Soc, 2010, 7: 646
-
[4]
[4] Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. Org Prep Proced Int, 2010, 42: 95
-
[5]
[5] Miao C X, He L N, Wang J Q, Wang J L. Adv Synth Catal, 2009, 351: 2209
-
[6]
[6] Cole A C, Jensen J L, Ntai I, Tran K L T, Weaver K J, Forbes D C, Davis J H. J Am Chem Soc, 2002, 124: 5962
-
[7]
[7] Arfan A, Bazureau J P. Org Process Res Dev, 2005, 9: 743
-
[8]
[8] Wasserscheid P, Sesing M, Korth W. Green Chem, 2002, 4: 134
-
[9]
[9] Ji S J, Jiang Z Q, Lu J, Loh T P. Synlett, 2004: 831
-
[10]
[10] Seddon K R, Stark A, Torres M J. Pure Appl Chem, 2000, 72: 2275
-
[11]
[11] Wasserscheid P, Keim W. Angew Chem Int Ed, 2000, 39: 3772
-
[12]
[12] Owens G S, Abu-Omar M M. ACS Symp Ser, 2002, 818: 321
-
[13]
[13] Anderson K, Goodrich P, Hardacre C, Rooney D W. Green Chem, 2003, 5: 448
-
[14]
[14] Wasserscheid P, van Hal R, Bösmann A. Green Chem, 2002, 4: 400
-
[15]
[15] Fraga-Dubreuil J, Bourahla K, Rahmouni M, Bazureau J P, Hamelin J. Catal Commun, 2002, 3: 185
-
[16]
[16] Garcia M T, Gathergood N, Scammells P J. Green Chem, 2005, 7: 9
-
[17]
[17] Gu Y L, Zhang J, Duan Z Y, Deng Y Q. Adv Synth Catal, 2005, 347: 512
-
[18]
[18] Kalita P, Kumar R. Microporous Mesoporous Mater, 2012, 149: 1
-
[19]
[19] Gathergood N, Garcia M T, Scammells P J. Green Chem, 2004, 6: 166
-
[20]
[20] Brock E D, Lewis D M, Yousaf T I, Harper H H. WO Patent 9951688. 1999
-
[21]
[21] Sakata G, Makino K, Karasawa Y. Heterocycles, 1988, 27: 2481
-
[22]
[22] Demeunynck M, Moucheron C, Kirsch-De Mesmaeker A. Tetrahedron Lett, 2002, 43: 261
-
[23]
[23] Baraznenok I L, Nenajdenko V G, Balenkova E S. Eur J Org Chem, 1999: 937
-
[24]
[24] Ali M M, Tasneem, Rajanna K C, Prakash P K S. Synlett, 2001: 251
-
[25]
[25] Palacios F, Ochoa de Retana A M, Oyarzabal J. Tetrahedron, 1999, 55: 5947
-
[26]
[26] Charpentier P, Lobregat V, Levacher V, Dupas G, Queguiner G, Bourguignon J. Tetrahedron Lett, 1998, 39: 4013
-
[27]
[27] Cho C S, Kim B T, Kim T J, Shim S C. Chem Commun, 2001: 2576
-
[28]
[28] Crousse B, Begue J P, Bonnet-Delpon D. J Org Chem, 2000, 65: 5009
-
[29]
[29] Lin X F, Cui S L, Wang Y G. Tetrahedron Lett, 2006, 47: 4509
-
[30]
[30] Lin X F, Cui S L, Wang Y G. Tetrahedron Lett, 2006, 47: 3127
-
[31]
[31] Beagley P, Blackie M A L, Chibale K, Clarkson C, Meijboom R, Moss J R, Smith P J, Su H. Dalton Trans, 2003: 3046
-
[32]
[32] 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
-
[33]
[33] Ma Z Z, Hano Y, Nomura T, Chen Y J. Bioorg Med Chem Lett, 2004, 14: 1193
-
[34]
[34] Denton T T, Zhang X D, Cashman J R. J Med Chem, 2005, 48: 224
-
[35]
[35] Fokialakis N, Magiatis P, Chinou I, Mitaku S, Tillequin F. Chem Pharm Bull, 2002, 50: 413
-
[36]
[36] Fossa P, Mosti L, Menozzi G, Marzano C, Baccichetti F, Bordin F. Bioorg Med Chem, 2002, 10: 743
-
[37]
[37] Ryckebusch A, Deprez-Poulain R, Maes L, Debreu-Fontaine M A, Mouray E, Grellier P, Sergheraert C. J Med Chem, 2003, 46: 542
-
[38]
[38] Morgan L R, Jursic B S, Hooper C L, Neumann D M, Thangaraj K, Leblanc B. Bioorg Med Chem Lett, 2002, 12: 3407
-
[39]
[39] Kouznetsov V V. Tetrahedron, 2009, 65: 2721
-
[40]
[40] Haghighi M G, Rashidi M, Nabavizadeh S M, Jamali S, Puddephatt R J. Dalton Trans, 2010, 39: 11396
-
[41]
[41] Baratta W, Fanfoni L, Magnolia S, Siega K, Rigo P. Eur J Inorg Chem, 2010: 1419
-
[42]
[42] Baratta W, Ballico M, Baldino S, Chelucci G, Herdtweck E, Siega K, Magnolia S, Rigo P. Chem Eur J, 2008, 14: 9148
-
[43]
[43] Prema D, Wiznycia A V, Scott B M T, Hilborn J, Desper J, Levy C J. Dalton Trans, 2007: 4788
-
[44]
[44] Mauzerall D, Westheimer F H. J Am Chem Soc, 1955, 77: 2261
-
[45]
[45] Godfraind T, Miller R, Wibo M. Pharmacol Rev, 1986, 38: 321
-
[46]
[46] Stout D M, Meyers A I. Chem Rev, 1982, 82: 223
-
[47]
[47] Janis R A, Triggle D J. J Med Chem, 1983, 26: 775
-
[48]
[48] Bossert F, Mayer H, Wehinger E. Angew Chem Int Ed, 1981, 20: 762
-
[49]
[49] Toussaint C, De Pauw L, Vienne A, Gevenois P A, Quintin J, Gelin M, Pasteels J L. Am J Kidney Dis, 1993, 21: 54
-
[50]
[50] Kawase M, Shah A, Gaveriya H, Motohashi N, Sakagami H, Varga A, Molnar J. Bioorg Med Chem, 2002, 10: 1051
-
[51]
[51] Ladani N K, Mungra D C, Patel M P, Patel R G. Chin Chem Lett, 2011, 22: 1407
-
[52]
[52] Wang S X, Li Z Y, Zhang J C, Li J T. Ultrason Sonochem, 2008, 15: 677
-
[53]
[53] Wang L M, Sheng J, Zhang L, Han J W, Fan Z Y, Tian H, Qian C T. Tetrahedron, 2005, 61: 1539
-
[54]
[54] Kumar A, Maurya R A. Tetrahedron, 2007, 63: 1946
-
[55]
[55] Undale K A, Shaikh T S, Gaikwad D S, Pore D M. C R Chim, 2011, 14: 511
-
[56]
[56] Maheswara M, Siddaiah V, Vasantha Damu G L, Rao C V. ARKIVOC, 2006, (ii): 201
-
[57]
[57] Katkar S S, Mohite P H, Gadekar L S, Arbad B R, Lande M K. Green Chem Lett Rev, 2010, 3: 287
-
[58]
[58] Safari J, Banitaba S H, Khalili S D. J Mol Catal A, 2011, 335: 46
-
[59]
[59] Surasani R, Kalita D, Dhanunjaya Rao A V, Yarbagi K, Chandrasekhar K B. J Fluorine Chem, 2012, 135: 91
-
[60]
[60] Heravi M M, Saeedi M, Karimi N, Zakeri M, Beheshtiha Y S, Davoodnia A. Synth Commun, 2010, 40: 523
-
[61]
[61] Nirmal J P, Dadhaniya P V, Patel M P, Patel R G. Indian J Chem B, 2010, 49: 587
-
[62]
[62] Khaligh N G. J Mol Catal A, 2011, 349: 63
-
[63]
[63] Khaligh N G. Catal Sci Technol, 2012, 2: 1633
-
[64]
[64] Zhao D S, Liu M S, Ge J J, Zhang J, Ren P B. Chin J Org Chem, 2012, 32: 2382
-
[65]
[65] Villagran C, Deetlefs M, Pitner W R, Hardacre C. Anal Chem, 2004, 76, 2118
-
[66]
[66] Cave G W V, Raston C L, Scott J L. Chem Commun, 2001: 2159
-
[67]
[67] Nagarapu L, Kumari M D, Kumari N V, Kantevari S. Catal Commun, 2007, 8: 1871
-
[68]
[68] Saikia L, Dutta D, Dutta D K. Catal Commun, 2012, 19: 1
-
[69]
[69] Baghbanian S M, Khaksar S, Mohammad Vahdat S, Farhang M, Tajbakhsh M. Chin Chem Lett, 2010, 21: 563
-
[70]
[70] Khojastehnezhad A, Moeinpour F, Davoodnia A. Chin Chem Lett, 2011, 22: 807
-
[71]
[71] 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
-
[72]
[72] Heydari A, Khaksar S, Tajbakhsh M, Bijanzadeh H R, J Fluorine Chem, 2009, 130: 609
-
[73]
[73] Hong M, Cai C, Yi W B. J Fluorine Chem, 2010, 131: 111
-
[74]
[74] Surasani R, Kalita D, Rao A V D, Yarbagi K, Chandrasekhar K B. J Fluorine Chem, 2012, 135: 91
-
[75]
[75] Donelson J L, Gibbs R A, De S K. J Mol Catal A, 2006, 256: 309
-
[76]
[76] Heravi M M, Bakhtiari K, Javadi N M, Bamoharram F F, Saeedi M, Oskooie H A. J Mol Catal A, 2007, 264: 50
-
[77]
[77] Tajbakhsh M, Alinezhad H, Norouzi M, Baghery S, Akbari M. J Mol Liquids, 2013, 177: 44
-
[78]
[78] Ko S, Yao C F. Tetrahedron, 2006, 62: 7293
-
[79]
[79] Kumar A, Maurya R A. Tetrahedron Lett, 2007, 48: 3887
-
[80]
[80] Sapkal S B, Shelke K F, Shingate B B, Shingare M S. Tetrahedron Lett, 2009, 50: 1754
-
[81]
[81] Saha M, Pal A K. Tetrahedron Lett, 2011, 52: 4872
-
[82]
[82] Zare A, Abi F, Moosavi-Zare A R, Beyzavi M H, Zolfigol M A. J Mol Liquids, 2013, 178: 113
-
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