Rice husk ash was used as a new, green, and cheap adsorbent for FeCl3. Characterization of the ob-tained reagent showed that rice husk ash supported FeCl2·2H2O was formed. This reagent is effi-cient at catalyzing the synthesis of multisubstituted quinolines by the Friedl?nder heteroannulation of o-aminoaryl ketones with ketones orβ-diketones under mild reaction conditions. This method-ology allows for the synthesis of a broad range of substituted quinolines in high yields and with excellent regioselectivity in the absence of a solvent.
参考文献
[1] | Larsen RD.;King AO.;Carroll JD.;Davis P.;Verhoeven TR. Reider PJ.;Labelle M.;Gauthier JY.;Xiang YB.;Zamboni RJ.;Corley EG. .PRACTICAL ROUTE TO A NEW CLASS OF LTD(4) RECEPTOR ANTAGONISTS[J].The Journal of Organic Chemistry,1996(10):3398-3405. |
[2] | Roma G;Di-Braccio M;Grossi G;Mattioli F;Ghia M .1,8-Naphthyridines IV. 9-substituted N,N-dialkyl-5-(alkylamino or cycloalkylamino) (1,2,4)triazolo(4,3-a)(1, 8)naphthyridine-6-carboxamides, new compounds with anti-aggressive and potent anti-inflammatory activities.[J].European Journal of Medicinal Chemistry: Chimie Therapeutique,2000(11):1021-1035. |
[3] | Michael J P .[J].Natural Product Reports,1997,14:605. |
[4] | Chen YL;Fang KC;Sheu JY;Hsu SL;Tzeng CC .Synthesis and antibacterial evaluation of certain quinolone derivatives.[J].Journal of Medicinal Chemistry,2001(14):2374-2377. |
[5] | Kalluraya B;Sreenivasa S .[J].FARMACO,1998,53:399. |
[6] | Dube D;Blouin M;Brideau C;Chan C C Desmarais S Either D Fal-gueyret J P Friesen R W Girard M Girard Y Guay J Riendeau D Tagari P Young R N .[J].Bioorganic and Medicinal Chemistry Letters,1998,8:1255. |
[7] | Maguire M P;Sheets K R;McVety K;Spada A P Zilberstein A .[J].Journal of Medicinal Chemistry,1994,37:2129. |
[8] | Agrawal A K;Jenekhe S A .[J].MACROMOLECULES,1991,24:6806. |
[9] | Zhang X;Shetty A S;Jenekhe S A .[J].MACROMOLECULES,1999,32:7422. |
[10] | Jenekhe S A;Lu L;Alam M M .[J].MACROMOLECULES,2001,34:7315. |
[11] | Skraup Z H .[J].Monatshefte fur Chemie,1880,1:316. |
[12] | Heindel N D;Brodof T A;Kogelschatz J E .[J].Journal of Heterocyclic Chemistry,1966,3:222. |
[13] | Hermecz I;Kereszturi G;Vasvari-Debreczy L .[J].ADVANCES IN HETEROCYCLIC CHEMISTRY,1992,54:1. |
[14] | Pfitzinger W .[J].JOURNAL FUR PRAKTISCHE CHEMIE,1886,33:100. |
[15] | Calaway P K;Henze H R .[J].Journal of the American Chemical Society,1939,61:1355. |
[16] | Friedl?nder P .[J].Chemische berichte,1882,15:2572. |
[17] | Fehnel E A .[J].Journal of Organic Chemistry,1966,31:2899. |
[18] | Long R;Schofield K.[J].Journal of the Chemical Society,1953:3161. |
[19] | Roberts E;Turner E E.[J].Journal of the Chemical Society,1927:1832. |
[20] | Dormer PG.;Eng KK.;Farr RN.;Humphrey GR.;McWilliams JC.;Reider PJ. Sager JW.;Volante RP. .Highly regioselective Friedlander annulations with unmodified ketones employing novel amine catalysts: Syntheses of 2-substituted quinolines, 1,8-naphthyridines, and related heterocycles[J].The Journal of Organic Chemistry,2003(2):467-477. |
[21] | Yadav JS;Reddy BVS;Sreedhar P;Rao RS;Nagaiah K .Silver phosphotungstate: A novel and recyclable heteropoly acid for Friedlander quinoline synthesis[J].Synthesis: International Journal of Methods in Synthetic Organic Chemistry,2004(14):2381-2385. |
[22] | Yadav JS;Rao PP;Sreenu D;Rao RS;Kumar VN;Nagaiah K;Prasad AR .Sulfamic acid: an efficient, cost-effective and recyclable solid acid catalyst for the Friedlander quinoline synthesis[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2005(42):7249-7253. |
[23] | Narasimhulu M;Reddy TS;Mahesh KC;Prabhakar P;Rao CB;Venkateswarlu Y .Silica supported perchloric acid: A mild and highly efficient heterogeneous catalyst for the synthesis of poly-substituted quinolines via Friedlander hetero-annulation[J].Journal of molecular catalysis, A. Chemical,2007(1/2):114-117. |
[24] | Das B;Damodar K;Chowdhury N;Kumar RA .Application of heterogeneous solid acid catalysts for Friedlander synthesis of quinolines[J].Journal of molecular catalysis, A. Chemical,2007(1/2):148-152. |
[25] | Ghassamipour S;Sardarian A R .[J].Tetrahedron Letters,2009,50:514. |
[26] | Arumugam P;Karthikeyan G;Atchudan R;Murlidharan D Perumal P T .[J].CHEMISTRY LETTERS,2005,34:314. |
[27] | Wu J;Zhang L;Diao TN .An expeditious approach to quinolines via Friedlander synthesis catalyzed by FeCl3 or Mg(ClO4)(2)[J].Synlett,2005(17):2653-2657. |
[28] | Varala R;Enugala R;Adapa SR .Efficient and rapid Friedlander synthesis of functionalized quinolines catalyzed by neodymium(III) nitrate hexahydrate[J].Synthesis: International Journal of Methods in Synthetic Organic Chemistry,2006(22):3825-3830. |
[29] | De S K;Gibbs R A .[J].Tetrahedron Letters,2005,46:1647. |
[30] | Dabiri M;Baghbanzadeh M;Arzroomchilar E .[J].HETEROCYCLES,2008,75:397. |
[31] | Wu J;Xia H G;Gao K .[J].Organic and Biological Chemistry,2006,4:126. |
[32] | Likhar, PR;Subhas, MS;Roy, S;Kantam, ML;Sridhar, B;Seth, RK;Biswas, S .Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines[J].Organic & biomolecular chemistry,2009(1):85-93. |
[33] | Dabiri M;Azimi S C;Bazgir A .[J].Monatshefte fur Chemie,2007,138:659. |
[34] | Ghorbani-Vaghei R;Akbari-Dadamahaleh S .[J].Tetrahedron Letters,2009,50:1055. |
[35] | Mierde H V;Van Der Voort P;Verpoort F .[J].Tetrahedron Letters,2009,50:201. |
[36] | Venu Gopal D;Srinivas N;Srinivas B;Kulkarni S J Subrahmanyam M .[J].Green Chemistry,2001,3:65. |
[37] | Hassan J;Sevignon M;Gozzi C;Schulz E Lemaire M .[J].CHEMICAL REVIEWS,2002,102:1359. |
[38] | Brouwer F .[D].Groningen:University of Groning-en,2011. |
[39] | Qiao X;Wang X;Mo Z .[J].Synthetic Metals,2001,122:449. |
[40] | He T;Wang J H;Liu T;Wu G T Xiong Z T Yin J Chu H L Zhang T Chen P .[J].Catalysis Today,2011,170:69. |
[41] | Likhar P R;Arundhathi R;Ghosh S;Kantam M L .[J].Journal of Molecular Catalysis A:Chemical,2009,302:142. |
[42] | Ahn B J;Gang M S;Chae K;Oh Y Shin J Chang W .[J].Journal of Industrial and Engineering Chemistry,2008,14:401. |
[43] | Choudhary V R;Jana S K .[J].Journal of Molecular Catalysis A:Chemical,2002,180:267. |
[44] | Salavati-Niasari M;Hasanalian J;Najafian H .[J].Journal of Molecular Catalysis A:Chemical,2004,209:209. |
[45] | Saleh M I;Farook A;Ab Rahman I;Othman R.Seramik Nusantara[M].Pulau Pinang:Universiti Sains,Malaysia,1990:261. |
[46] | Rafiee E;Khodayari M;Shahebrahimi S;Joshaghani M .[J].Journal of Molecular Catalysis A:Chemical,2011,351:204. |
[47] | Srivastava VC;Mall ID;Mishra IM .Removal of cadmium(II) and zinc(II) metal ions from binary aqueous solution by rice husk ash[J].Colloids and Surfaces, A. Physicochemical and Engineering Aspects,2008(2/3):172-184. |
[48] | Srivastava V C;Mall I D;Mishra I M .[J].Chemical Engineering Progress,2009,48:370. |
[49] | Feng QG;Lin QY;Gong FZ;Sugita S;Shoya M .Adsorption of lead and mercury by rice husk ash[J].Journal of Colloid and Interface Science,2004(1):1-8. |
[50] | Adam F;Kandasamy K;Balakrishnan S .Iron incorporated heterogeneous catalyst from rice husk ash[J].Journal of Colloid and Interface Science,2006(1):137-143. |
[51] | Lambert J B;Shurvell H F;Lightner D A;Cooks R G.Organic Struc-tural Spectroscopy[M].Upper Saddle River,NJ:Prentice Hall,1998:191. |
[52] | Stark W J;Strobel R;Guenther D;Pratsinis S E Baiker A .[J].Journal of Materials Chemistry,2002,12:3620. |
[53] | Chang F W;Kuo W Y;Lee K C .[J].Applied Catalysis A:General,2003,246:253. |
[54] | Yalcin N;Sevinc V .[J].CERAMICS INTERNATIONAL,2001,27:219. |
[55] | Battiston A A;Bitter J H;de Groot F M F;Overweg A R Stephan O van Bokhoven J A Kooyman P J van der Spek C Vankó G Kon-ingsberger D C .[J].Journal of Catalysis,2003,213:251. |
[56] | Shirini F;Akbari-Dadamahaleh S;Mohammad-Khah A .[J].Journal of Molecular Catalysis A:Chemical,2012,363-364:10. |
[57] | Shirini F;Akbari-Dadamahaleh S;Mohammad-Khah A;Aliakbar A R .[J].Cr Chimie,2013,16:207. |
[58] | Wu J L;Hou R S;Wang H M;Kang I J Chen L C .[J].Journal of The Chinese Ceramic Society,2009,56:867. |
[59] | Zolfigol MA;Salehi P;Ghaderi A;Shiri M;Tanbakouchian Z .An eco-friendly procedure for the synthesis of polysubstituted quinolines under aqueous media[J].Journal of molecular catalysis, A. Chemical,2006(1/2):253-258. |
[60] | Pasha M A;Jayashankara V P;Mahammed K A .[J].Indian Journal of Chemistry Section B-Organic Chemistry Including Medicin,2008,47B:1160. |
[61] | Palimkar SS.;Siddiqui SA.;Daniel T.;Lahoti RJ.;Srinivasan KV. .Ionic liquid-promoted regiospecific Friedlander annulation: Novel synthesis of quinolines and fused polycyclic quinolines[J].The Journal of Organic Chemistry,2003(24):9371-9378. |
[62] | Hou R S;Wu J L;Cheng H T;Xie Y T Chen L C .[J].Journal of The Chinese Ceramic Society,2008,55:915. |
[63] | Zolfigol M A;Salehi P;Ghaderi A;Shiri M .[J].CATALYSIS COMMUNICATIONS,2007,8:1214. |
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%