|
OALib Journal期刊
ISSN: 2333-9721
费用：99美元
|
|
|
|
One-potmulticomponentsynthesisofunsymmetricalpolyhydroquinolinederivativeswith1,1’-butylenebispyridiniumhydrogensulfateasanefficient,halogen-freeandreusableBr？nstedionicliquidcatalyst
DOI: 10.1016/S1872-2067(14)60087-5, PP. 1497-1503
Keywords: Unsymmetricpolyhydroquinolines,Br？nstedacidicionicliquid,Ultrasonication,Multicomponent,Solvent-free
Abstract:
？1,1'-Butylenebispyridiniumhydrogensulfateisanefficient,halogen-freeandreusableBr？nstedionicliquidcatalystforthesynthesisofethyl-4-aryl/heteryl-hexahydro-trimehtyl-5-oxoquinoline-3-carboxylatesbytheone-potcondensationofdimedone,aryl/heterylaldehydes,ethylacetoacetate,andammoniumacetateundersolvent-freeconditions.Thismethodhastheadvantagesofhighyield,cleanreaction,simplemethodology,andshortreactiontime.Theionicliquidcanberecycledfivetimeswithoutsignificantlossofthecatalyticactivity.
| [1] | Nirmal J P, Dadhaniya P V, Patel M P, Patel R G. Indian J Chem B, 2010, 49: 587
|
| [2] | Khaligh N G. J Mol Catal A, 2011, 349: 63
|
| [3] | Khaligh N G. Catal Sci Technol, 2012, 2: 1633
|
| [4] | Zhao D S, Liu M S, Ge J J, Zhang J, Ren P B. Chin J Org Chem, 2012, 32: 2382
|
| [5] | Villagran C, Deetlefs M, Pitner W R, Hardacre C. Anal Chem, 2004, 76, 2118
|
| [6] | Donelson J L, Gibbs R A, De S K. J Mol Catal A, 2006, 256: 309
|
| [7] | Heravi M M, Bakhtiari K, Javadi N M, Bamoharram F F, Saeedi M, Oskooie H A. J Mol Catal A, 2007, 264: 50
|
| [8] | Tajbakhsh M, Alinezhad H, Norouzi M, Baghery S, Akbari M. J Mol Liquids, 2013, 177: 44
|
| [9] | Sapkal S B, Shelke K F, Shingate B B, Shingare M S. Tetrahedron Lett, 2009, 50: 1754
|
| [10] | Parvulescu V I, Hardacre C. Chem Rev, 2007, 107: 2615
|
| [11] | Rogers R D, Seddon K R. Ionic Liquids: Industrial Applications to Green Chemistry. American Chemical Society, Washington DC, 2002
|
| [12] | 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
|
| [13] | Seddon K R, Stark A, Torres M J. Pure Appl Chem, 2000, 72: 2275
|
| [14] | Anderson K, Goodrich P, Hardacre C, Rooney D W. Green Chem, 2003, 5: 448
|
| [15] | Wasserscheid P, van Hal R, B？smann A. Green Chem, 2002, 4: 400
|
| [16] | Fraga-Dubreuil J, Bourahla K, Rahmouni M, Bazureau J P, Hamelin J. Catal Commun, 2002, 3: 185
|
| [17] | Demeunynck M, Moucheron C, Kirsch-De Mesmaeker A. Tetrahedron Lett, 2002, 43: 261
|
| [18] | Palacios F, Ochoa de Retana A M, Oyarzabal J. Tetrahedron, 1999, 55: 5947
|
| [19] | Lin X F, Cui S L, Wang Y G. Tetrahedron Lett, 2006, 47: 4509
|
| [20] | Lin X F, Cui S L, Wang Y G. Tetrahedron Lett, 2006, 47: 3127
|
| [21] | Beagley P, Blackie M A L, Chibale K, Clarkson C, Meijboom R, Moss J R, Smith P J, Su H. Dalton Trans, 2003: 3046
|
| [22] | 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
|
| [23] | Ma Z Z, Hano Y, Nomura T, Chen Y J. Bioorg Med Chem Lett, 2004, 14: 1193
|
| [24] | Denton T T, Zhang X D, Cashman J R. J Med Chem, 2005, 48: 224
|
| [25] | Haghighi M G, Rashidi M, Nabavizadeh S M, Jamali S, Puddephatt R J. Dalton Trans, 2010, 39: 11396
|
| [26] | Baratta W, Fanfoni L, Magnolia S, Siega K, Rigo P. Eur J Inorg Chem, 2010: 1419
|
| [27] | Baratta W, Ballico M, Baldino S, Chelucci G, Herdtweck E, Siega K, Magnolia S, Rigo P. Chem Eur J, 2008, 14: 9148
|
| [28] | Prema D, Wiznycia A V, Scott B M T, Hilborn J, Desper J, Levy C J. Dalton Trans, 2007: 4788
|
| [29] | Mauzerall D, Westheimer F H. J Am Chem Soc, 1955, 77: 2261
|
| [30] | Janis R A, Triggle D J. J Med Chem, 1983, 26: 775
|
| [31] | Bossert F, Mayer H, Wehinger E. Angew Chem Int Ed, 1981, 20: 762
|
| [32] | Toussaint C, De Pauw L, Vienne A, Gevenois P A, Quintin J, Gelin M, Pasteels J L. Am J Kidney Dis, 1993, 21: 54
|
| [33] | Kawase M, Shah A, Gaveriya H, Motohashi N, Sakagami H, Varga A, Molnar J. Bioorg Med Chem, 2002, 10: 1051
|
| [34] | Ladani N K, Mungra D C, Patel M P, Patel R G. Chin Chem Lett, 2011, 22: 1407
|
| [35] | Wang S X, Li Z Y, Zhang J C, Li J T. Ultrason Sonochem, 2008, 15: 677
|
| [36] | Wang L M, Sheng J, Zhang L, Han J W, Fan Z Y, Tian H, Qian C T. Tetrahedron, 2005, 61: 1539
|
| [37] | Kumar A, Maurya R A. Tetrahedron, 2007, 63: 1946
|
| [38] | Maheswara M, Siddaiah V, Vasantha Damu G L, Rao C V. ARKIVOC, 2006, (ii): 201
|
| [39] | Katkar S S, Mohite P H, Gadekar L S, Arbad B R, Lande M K. Green Chem Lett Rev, 2010, 3: 287
|
| [40] | Surasani R, Kalita D, Dhanunjaya Rao A V, Yarbagi K, Chandrasekhar K B. J Fluorine Chem, 2012, 135: 91
|
| [41] | Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. J Iran Chem Soc, 2010, 7: 646
|
| [42] | Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A. Org Prep Proced Int, 2010, 42: 95
|
| [43] | Miao C X, He L N, Wang J Q, Wang J L. Adv Synth Catal, 2009, 351: 2209
|
| [44] | Arfan A, Bazureau J P. Org Process Res Dev, 2005, 9: 743
|
| [45] | Wasserscheid P, Sesing M, Korth W. Green Chem, 2002, 4: 134
|
| [46] | Ji S J, Jiang Z Q, Lu J, Loh T P. Synlett, 2004: 831
|
| [47] | Wasserscheid P, Keim W. Angew Chem Int Ed, 2000, 39: 3772
|
| [48] | Owens G S, Abu-Omar M M. ACS Symp Ser, 2002, 818: 321
|
| [49] | Garcia M T, Gathergood N, Scammells P J. Green Chem, 2005, 7: 9
|
| [50] | Gu Y L, Zhang J, Duan Z Y, Deng Y Q. Adv Synth Catal, 2005, 347: 512
|
| [51] | Kalita P, Kumar R. Microporous Mesoporous Mater, 2012, 149: 1
|
| [52] | Gathergood N, Garcia M T, Scammells P J. Green Chem, 2004, 6: 166
|
| [53] | Brock E D, Lewis D M, Yousaf T I, Harper H H. WO Patent 9951688. 1999
|
| [54] | Sakata G, Makino K, Karasawa Y. Heterocycles, 1988, 27: 2481
|
| [55] | Baraznenok I L, Nenajdenko V G, Balenkova E S. Eur J Org Chem, 1999: 937
|
| [56] | Ali M M, Tasneem, Rajanna K C, Prakash P K S. Synlett, 2001: 251
|
| [57] | Charpentier P, Lobregat V, Levacher V, Dupas G, Queguiner G, Bourguignon J. Tetrahedron Lett, 1998, 39: 4013
|
| [58] | Cho C S, Kim B T, Kim T J, Shim S C. Chem Commun, 2001: 2576
|
| [59] | Crousse B, Begue J P, Bonnet-Delpon D. J Org Chem, 2000, 65: 5009
|
| [60] | Fokialakis N, Magiatis P, Chinou I, Mitaku S, Tillequin F. Chem Pharm Bull, 2002, 50: 413
|
| [61] | Fossa P, Mosti L, Menozzi G, Marzano C, Baccichetti F, Bordin F. Bioorg Med Chem, 2002, 10: 743
|
| [62] | Ryckebusch A, Deprez-Poulain R, Maes L, Debreu-Fontaine M A, Mouray E, Grellier P, Sergheraert C. J Med Chem, 2003, 46: 542
|
| [63] | Morgan L R, Jursic B S, Hooper C L, Neumann D M, Thangaraj K, Leblanc B. Bioorg Med Chem Lett, 2002, 12: 3407
|
| [64] | Kouznetsov V V. Tetrahedron, 2009, 65: 2721
|
| [65] | Godfraind T, Miller R, Wibo M. Pharmacol Rev, 1986, 38: 321
|
| [66] | Stout D M, Meyers A I. Chem Rev, 1982, 82: 223
|
| [67] | Undale K A, Shaikh T S, Gaikwad D S, Pore D M. C R Chim, 2011, 14: 511
|
| [68] | Safari J, Banitaba S H, Khalili S D. J Mol Catal A, 2011, 335: 46
|
| [69] | Heravi M M, Saeedi M, Karimi N, Zakeri M, Beheshtiha Y S, Davoodnia A. Synth Commun, 2010, 40: 523
|
| [70] | Cave G W V, Raston C L, Scott J L. Chem Commun, 2001: 2159
|
| [71] | Nagarapu L, Kumari M D, Kumari N V, Kantevari S. Catal Commun, 2007, 8: 1871
|
| [72] | Saikia L, Dutta D, Dutta D K. Catal Commun, 2012, 19: 1
|
| [73] | Baghbanian S M, Khaksar S, Mohammad Vahdat S, Farhang M, Tajbakhsh M. Chin Chem Lett, 2010, 21: 563
|
| [74] | Khojastehnezhad A, Moeinpour F, Davoodnia A. Chin Chem Lett, 2011, 22: 807
|
| [75] | 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
|
| [76] | Heydari A, Khaksar S, Tajbakhsh M, Bijanzadeh H R, J Fluorine Chem, 2009, 130: 609
|
| [77] | Hong M, Cai C, Yi W B. J Fluorine Chem, 2010, 131: 111
|
| [78] | Surasani R, Kalita D, Rao A V D, Yarbagi K, Chandrasekhar K B. J Fluorine Chem, 2012, 135: 91
|
| [79] | Ko S, Yao C F. Tetrahedron, 2006, 62: 7293
|
| [80] | Kumar A, Maurya R A. Tetrahedron Lett, 2007, 48: 3887
|
| [81] | Saha M, Pal A K. Tetrahedron Lett, 2011, 52: 4872
|
| [82] | Zare A, Abi F, Moosavi-Zare A R, Beyzavi M H, Zolfigol M A. J Mol Liquids, 2013, 178: 113
|
Full-Text
|
|
Contact Us
service@oalib.com QQ:3279437679 
WhatsApp +8615387084133
|
|
