A simple and facile synthesis of 12-arylbenzo[g]indeno[2,1-b]quinoline-6,11,13-trione deriv-atives was accomplished by the one-pot condensation of 2-hydroxynaphthalene-1,4-dione, aryl aldehydes, 2H-indene-1,3-dione, and ammonium acetate under solvent-free conditions in the presence of a Br?nsted ionic liquid catalyst, namely 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate.
参考文献
| [1] | Brock E D;Lewis D M;Yousaf T I;Harper H H .[P].WO Patent 9 951 688,1999. |
| [2] | Beagley P;Blackie M A L;Chibale K;Clarkson C,Meijboom R,Moss J R,Smith P J,Su H.[J].Dalton Trans,2003:3046. |
| [3] | Sawada Y;Kayakiri H;Abe Y;Mizutani T Inamura N Asano M Ha-tori C Aramori I Oku T Tanaka H .[J].Journal of Medicinal Chemistry,2004,47:2853. |
| [4] | Ma Z Z;Hano Y;Nomura T;Chen Y J .[J].Bioorganic and Medicinal Chemistry Letters,2004,14:1193. |
| [5] | Denton TT;Zhang XD;Cashman JR .5-substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6[J].Journal of Medicinal Chemistry,2005(1):224-239. |
| [6] | Sakata G;Makino K;Karasawa Y .[J].HETEROCYCLES,1988,27:2481. |
| [7] | Demeunynck M;Moucheron C;Mesmaeker A K D .[J].Tetrahedron Letters,2002,43:261. |
| [8] | Lin XF;Cui SL;Wang YG .A highly efficient synthesis of 1,2,3,4-tetrahydroquinolines by molecular iodine-catalyzed domino reaction of anilines with cyclic enol ethers[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2006(26):4509-4512. |
| [9] | Tsai, A.S.;Tauchert, M.E.;Bergman, R.G.;Ellman, J.A. .Rhodium(III)-catalyzed arylation of Boc-imines via C-H bond functionalization[J].Journal of the American Chemical Society,2011(5):1248-1250. |
| [10] | Kakiuchi, F;Kochi, T;Mutsutani, H;Kobayashi, N;Urano, S;Sato, M;Nishiyama, S;Tanabe, T .Palladium-Catalyzed Aromatic C-H Halogenation with Hydrogen Halides by Means of Electrochemical Oxidation[J].Journal of the American Chemical Society,2009(32):11310-11311. |
| [11] | Yu, WY;Sit, WN;Lai, KM;Zhou, ZY;Chan, ASC .Palladium-catalyzed oxidative ethoxycarbonylation of aromatic C-H bond with diethyl azodicarboxylate[J].Journal of the American Chemical Society,2008(11):3304-3306. |
| [12] | Aramoto H;Obora Y;Ishii Y .N-Heterocyclization of Naphthylamines with 1,2-and 1,3-Diols Catalyzed by an Iridium Chloride/BINAP System[J].The Journal of Organic Chemistry,2009(2):628-633. |
| [13] | Wang XS;Li Q;Yao CS;Tu SJ .An efficient method for the synthesis of benzo[f]quinoline and benzo[a]phenanthridine derivatives catalyzed by iodine by a three-component reaction of arenecarbaldehyde, naphthalen-2-amine, and cyclic ketone[J].European journal of organic chemistry,2008(20):3513-3518. |
| [14] | Kozlov N G;Gusak K N .[J].Russian Journal of Organic Chemistry,2008,44:1049. |
| [15] | Hewlins M J E;Salter R.[J].Synthesis,2007:2157. |
| [16] | Yadav JS.;Srinivas R.;Madhuri C.;Ramalingam T.;Reddy BVS. .Lithium perchlorate/diethylether catalyzed aza-Diels-Alder reaction: An expeditious synthesis of pyrano, indeno quinolines and phenanthridines[J].Synlett,2001(2):240-242. |
| [17] | Lu X L;Petersen J L;Wang K K .[J].Organic Letters,2003,5:3277. |
| [18] | Cho CS.;Kim BT.;Choi HJ.;Kim TJ.;Shim SC. .Ruthenium-catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines[J].Tetrahedron,2003(40):7997-8002. |
| [19] | Sunami T;Nishio K;Kanzawa F;Fukuoka K Kudoh S Yoshikawa J Saijo N .[J].Cancer Chemotherapy and Pharmacology,1999,43:394. |
| [20] | Antony S;Jayaraman M;Laco G;Kohlhagen G;Kohn KW;Cushman M;Pommier Y .Differential induction of topoisomerase I-DNA cleavage complexes by the indenoisoquinoline MJ-III-65 (NSC 706744) and camptothecin: base sequence analysis and activity against camptothecin-resistant topoisomerases I.[J].Cancer research,2003(21):7428-7435. |
| [21] | Mansake R H F;Kulka M .[J].organic reaction,1953,7:59. |
| [22] | Povarov L S .[J].Russian Chemical Reviews,1967,36:656. |
| [23] | Kouznetsov, VV .Recent synthetic developments in a powerful imino Diels-Alder reaction (Povarov reaction): application to the synthesis of N-polyheterocycles and related alkaloids[J].Tetrahedron,2009(14):2721-2750. |
| [24] | Haghighi, M.G.;Rashidi, M.;Nabavizadeh, S.M.;Jamali, S.;Puddephatt, R.J. .Cyclometalated organoplatinum(ii) complexes: First example of a monodentate benzo[h]quinolyl ligand and a complex with bridging bis(diphenylphosphino) ethane[J].Dalton transactions: An international journal of inorganic chemistry,2010(47):11396-11402. |
| [25] | Baratta, W;Fanfoni, L;Magnolia, S;Siega, K;Rigo, P .Benzo[h]quinoline Pincer Ruthenium and Osmium Catalysts for Hydrogenation of Ketones[J].European journal of inorganic chemistry,2010(9):1419-1423. |
| [26] | Prema D;Wiznycia AV;Scott BMT;Hilborn J;Desper J;Levy CJ .Dinuclear zinc(II) complexes of symmetric Schiff-base ligands with extended quinoline sidearms[J].Dalton transactions: An international journal of inorganic chemistry,2007(42):4788-4796. |
| [27] | Bierer DE;Dubenko LG;Zhang P;Lu Q;Imbach PA;Garofalo AW;Phuan PW;Fort DM;Litvak J;Gerber RE;Sloan B;Luo J;Cooper R;Reaven GM .Antihyperglycemic activities of cryptolepine analogues: an ethnobotanical lead structure isolated from Cryptolepis sanguinolenta.[J].Journal of Medicinal Chemistry,1998(15):2754-2764. |
| [28] | Venugopalan B;Bapat C P;DeSouza E P;DeSouza N J .[J].INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL,1992,31:35. |
| [29] | Deady L W;Desneves J;Kaye A J;Finlay G J Baguley B C Denny W A .[J].Bioorganic and Medicinal Chemistry Letters,2000,8:977. |
| [30] | Rampa A;Bisi A;Belluti F;Gobbi S Valenti P Andrisano V Cavrini V Cavalli A Recanatini M .[J].Bioorganic and Medicinal Chemistry Letters,2000,8:497. |
| [31] | Lankin D C;Zimmer H .[J].Journal of Heterocyclic Chemistry,1973,10:1035. |
| [32] | Gorlitzer K;Weber J .[J].ARCHIV DER PHARMAZIE,1981,314:76. |
| [33] | Lu X L;Petersen J L;Wang K K .[J].Organic Letters,2003,5:3277. |
| [34] | Sawada Y;Kayakiri H;Abe Y;Imai K Mizutani T Inamura N Asano M Aramori I Hatori C Katayama A Oku T Tanaka H .[J].Journal of Medicinal Chemistry,2004,47:1617. |
| [35] | Groisy-Delcey M;Groisy A;Carrez D;Huel C Chiaroni A Ducrot P Bisagni E Jin L Leclercq G .[J].Bioorganic and Medicinal Chemistry Letters,2000,8:2629. |
| [36] | Cheng C H;Chen R M;Huang C W;Yang C C .[P].US Patent 0025995A1,2005. |
| [37] | Kim J I;Shin I S;Kim H;Lee J K .[J].Journal of the American Chemical Society,2005,127:1614. |
| [38] | Thompson M E;Ma B W;Djurovich P .[P].US Patent 0164031A1,2005. |
| [39] | Parvulescu V I;Hardacre C .[J].CHEMICAL REVIEWS,2007,107:2615. |
| [40] | Rogers R D;Seddon K R.Ionic Liquids:Industrial Applications forGreen Chemistry[M].Washington:Am Chem Soc,2002 |
| [41] | Cole A C;Jensen J L;Ntai I;Tran K L T Weaver K J Forbes D C Davis J H Jr .[J].Journal of the American Chemical Society,2002,124:5962. |
| [42] | Gu Y L;Shi F;Deng Y Q .[J].Journal of Molecular Catalysis A:Chemical,2004,212:71. |
| [43] | Niknam K;Damya M .[J].Journal of The Chinese Ceramic Society,2009,56:659. |
| [44] | Tajik, H.;Niknam, K.;Sarrafan, M. .1-butyl-3-methylimidazolium hydrogen sulfate ([bmim]-HSO _4)-mediated synthesis of polysubstituted quinolines[J].Synthetic Communications,2011(13/15):2103-2114. |
| [45] | Khaligh N G;Mihankhah T.[J].Research on Chemical Intermediates |
| [46] | Khaligh N G;Mihankhah T .[J].催化学报,2013,34:2167. |
| [47] | Khaligh N G .[J].催化学报,2014,35:474. |
| [48] | Khaligh N G .[J].Journal of Molecular Catalysis A:Chemical,2011,349:63. |
| [49] | Greenberg A E;Trussell R R;Clesceri L S;Franson M A H.Standard Methods for the Examination of Water and Wastewater.16th Ed[M].Washington:American Public Health Association,1985:532. |
| [50] | To Q H;Lee Y R;Kim S H .[J].Bulletin of the Korean Chemical Society,2012,33:1170. |
| [51] | Wang X S;Zhang M M;Jiang H;Yao C S Tu S J .[J].Tetrahedron,2007,63:4439. |
| [52] | Sarkar, A.;Roy, S.R.;Chakraborti, A.K. .Ionic liquid catalysed reaction of thiols with α,β-unsaturated carbonyl compounds-remarkable influence of the C-2 hydrogen and the anion[J].Chemical communications,2011(15):4538-4540. |
| [53] | OECD Chemical Group.Ready Biodegradability:Modified OECD Screening Test.Method 301 E.OECD Revised Guidelines for Tests for Ready Biodegradability[M].Paris,France,1993 |
| [54] | Garcia MT;Gathergood N;Scammells PJ .Biodegradable ionic liquids - Part II. Effect of the anion and toxicology[J].Green chemistry,2005(1):9-14. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%