A straightforward and general method has been developed for the synthesis of Cs-unsubstitiuted 1,4-dihydropyridines by a reaction using dimedone,acetophenone,aromatic aldehydes,and ammonium acetate in the presence of a catalytic amount of Co nanoparticles as a heterogeneous and eco-friendly catalyst with high catalytic activity at room temperature under solvent-free conditions.This catalyst is easily separated by magnetic devices and can be reused without any apparent loss of activity for the reaction.In addition,it is very interesting that when using Co nanoparticles as a catalyst,spatially-hindered aldehydes such as 2-methoxy-,2-fluoro-,and 2-chloro-aldehydes are suitable for this reaction.
参考文献
| [1] | Safari J;Khalili S D;Rezaei M;Banitaba S H Meshkani F .[J].Monatshefte Fur Chemie,2010,141:1339. |
| [2] | Peng Q;Yang Y;Yuan Y .[J].Journal of Molecular Catalysis A:Chemical,2004,219:175. |
| [3] | Fu H;Li M;Chen H;Li X .[J].Journal of Molecular Catalysis A:Chemical,2006,259:156. |
| [4] | Paulik F E .[J].Catalysis Review,1972,6:49. |
| [5] | Beller M;Comils B;Frohning C D;Kohlpaintner C W .[J].Journal of Molecular Catalysis A:Chemical,1995,104:17. |
| [6] | Ungvary F .[J].Coordination Chemistry Reviews,2007,251:2087. |
| [7] | Wen F;Bnnemann H;Jiang J;Lu D Wang Y Jin Z .[J].Applied Organometallic Chemistry,2005,19:81. |
| [8] | Bruss AJ;Gelesky MA;Machado G;Dupont J .Rh(0) nanoparticles as catalyst precursors for the solventless hydroformylation of olefins[J].Journal of molecular catalysis, A. Chemical,2006(1/2):212-218. |
| [9] | Ma L;Peng Q;He D .[J].Catalysis Letters,2009,130:137. |
| [10] | Anastas P T;Warner J C.Green Chemistry:Theory and Practice[M].Oxford:Oxford University Press,1998 |
| [11] | Kalinski C;Lemoine H;Schmidt J;Burdack C,Kolb J,Umkehrer M,Ross G.[J].Synlett:Accounts and Rapid Communications In Synthetic Organic Chemistry,2008:4007. |
| [12] | Debache A;Ghalem W;Boulcina R;Belfaitah A Rhouati S Carboni B .[J].Tetrahedron Letters,2009,50:5248. |
| [13] | Klusa V .[J].Drugs of the Future,1995,20:135. |
| [14] | Bretzel R G;Bollen C C;Maeser E;Federlin K F .[J].American Journal of Kidney Diseases,1993,21:53. |
| [15] | Bretzel R G;Bollen C C;Maeser E;Federlin K F .[J].Drugs of the Future,1992,17:465. |
| [16] | Rainer B;Volker G .[J].Drugs of the Future,1995,20:499. |
| [17] | Janis RA;Triggle D J .[J].Journal of Medicinal Chemistry,1983,26:775. |
| [18] | Boecker R H;Guengerich F P .[J].Journal of Medicinal Chemistry,1986,29:1596. |
| [19] | Gaudio A C;Korolkovas A;Tkahata Y .[J].Journal of Pharmaceutical Sciences,1994,83:1110. |
| [20] | Gordeev MF.;Gordon EM.;Patel DV. .APPROACHES TO COMBINATORIAL SYNTHESIS OF HETEROCYCLES - A SOLID-PHASE SYNTHESIS OF 1,4-DIHYDROPYRIDINES[J].The Journal of Organic Chemistry,1996(3):924-928. |
| [21] | Svetlik J;Veizerova L;Kittmann V .[J].Tetrahedron Letters,2008,49:3520. |
| [22] | Suzuki I;Suzumura Y;Takeda K .[J].Tetrahedron Letters,2006,47:7861. |
| [23] | Shaabani A;Bazgir A;Teimouri F .[J].Tetrahedron Letters,2003,44:857. |
| [24] | Li M;Zuo ZQ;Wen LR;Wang SW .Microwave-assisted combinatorial synthesis of hexa-substituted 1,4-dihydropyridines scaffolds using one-pot two-step multicomponent reaction followed by a S-alkylation[J].Journal of combinatorial chemistry,2008(3):436-441. |
| [25] | Sabitha G;Reddy G S K;Reddy C S;Yadav J S .[J].Tetrahedron Letters,2003,44:4129. |
| [26] | Heravi MM;Bakhtiari K;Javadi NM;Bamoharram FF;Saeedi M;Oskooie HA .K-7[PW11CoO40]-catalyzed one-pot synthesis of polyhydroquinoline derivatives via the Hantzsch three component condensation[J].Journal of molecular catalysis, A. Chemical,2007(1/2):50-52. |
| [27] | Cherkupally SR;Mekala R .P-TSA catalyzed facile and efficient synthesis of polyhydroquinoline derivatives through Hantzsch multi-component condensation[J].Chemical and Pharmaceutical Bulletin,2008(7):1002-1004. |
| [28] | Wang LM;Sheng J;Zhang L;Han JW;Fan ZY;Tian H;Qian CT .Facile Yb(OTf)(3) promoted one-pot synthesis of polyhydroquinoline derivatives through Hantzsch reaction[J].Tetrahedron,2005(6):1539-1543. |
| [29] | Ji S;Jiang Z Q;Lu J;Loh T P.[J].Synlett:Accounts and Rapid Communications In Synthetic Organic Chemistry,2004:831. |
| [30] | Sainani J B;Shah A C;Arya V P .[J].Indian Journal of Chemistry Section B:Organic Chemistry Including Medicinal Chemistry,1994,33B:526. |
| [31] | KumarA;Maurya RA .[J].Tetrahedron Letters,2007,48:3887. |
| [32] | Ko S;Yao C F .[J].Tetrahedron,2006,62:7293. |
| [33] | Tu SJ;Yan S;Cao XD;Wu SS;Zhang XH;Hao WJ;Han ZG;Shi F .A facile and expeditious microwave-assisted synthesis of 4-aryl-2-ferrocenyl-quinoline derivatives via multi-component reaction[J].Journal of Organometallic Chemistry,2009(1):91-96. |
| [34] | Zang H;Zhang Y;Zang Y;Cheng B-W .[J].Ultrasonics Sonochemistry,2010,17:495. |
| [35] | Tu S J;Zhou J F;Deng X;Cai P J Wang H Feng J C .[J].Chinese Journal of Inorganic Chemistry,2001,21:313. |
| [36] | Wang XS.;Shi DQ.;Tu SJ. .A convenient synthesis of 2,4-diarylpolyhydroquinoline derivations in the presence of ammonium acetate[J].Synthetic Communications,2002(22):3449-3454. |
| [37] | Chen WY;Lu J;Jin JR .Synthesis of polyhydroquinoline derivatives under solvent-free conditions[J].Letters in organic chemistry,2006(4):317-319. |
| [38] | Kim S W;Son S U;Lee S S;Hyeon T,Chung Y K.[J].Chemical Communications,2001:2212. |
| [39] | Safari J;Banitaba S H;Khalili S D .[J].Journal of Molecular Catalysis A:Chemical,2011,335:46. |
| [40] | Guo F;Zheng H;Yang Z;Qian Y .[J].Materials Letters,2002,56:906. |
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%