Amino-functionalized SBA-15(SBA-Pr-NH2) has been used as a new basic nanocatalyst in the one-pot synthesis of spirooxindole derivatives via the three-component condensation reaction of isatins, activated methylene reagents, and dimedone in an aqueous medium. SBA-Pr-NH2 has been established as an efficient heterogeneous nanoporous solid basic catalyst (pore size of 6 nm) that can be easily handled and removed from the reaction mixture by simple filtration, and also recovered and reused without noticeable loss of reactivity.
参考文献
| [1] | Longeon A;Guyot M;Vacelet J .[J].Experientia,1990,46:548. |
| [2] | Trost B M;Brennan M K.[J].Synthesis,2009:3003. |
| [3] | Kang TH;Matsumoto K;Tohda M;Murakami Y;Takayama H;Kitajima M;Aimi N;Watanabe H .Pteropodine and isopteropodine positively modulate the function of rat muscarinic M(1) and 5-HT(2) receptors expressed in Xenopus oocyte.[J].European Journal of Pharmacology: An International Journal,2002(1/2):39-45. |
| [4] | Cui CB.;Osada H.;Kakeya H. .NOVEL MAMMALIAN CELL CYCLE INHIBITORS, SPIROTRYPROSTATINS A AND B, PRODUCED BY ASPERGILLUS FUMIGATUS, WHICH INHIBIT MAMMALIAN CELL CYCLE AT G2/M PHASE[J].Tetrahedron,1996(39):12651-12666. |
| [5] | Bhaskar,G.;Arun,Y.;Balachandran,C.;Saikumar,C.;Perumal,P.T..Synthesis of novel spirooxindole derivatives by one pot multicomponent reaction and their antimicrobial activity[J].European Journal of Medicinal Chemistry: Chimie Therapeutique,2012:79-91. |
| [6] | Jiang X;Sun Y;Yao J;Cao Y Kai M He N Zhang X Wang Y Wang R .[J].Advanced Synthesis and Catalysis,2012,354:917. |
| [7] | Galliford C V;Scheidt K A .[J].Angewandte Chemie International Edition,2007,46:8748. |
| [8] | Da Silva J F M;Garden S J;Pinto A C .[J].Journal of the Brazilian Chemical Society,2001,12:273. |
| [9] | Lashgari N;Mohammadi Ziarani G .[J].Arkivoc,2012,i:277. |
| [10] | Shanthi G;Subbulakshmi G;Perumal PT .A new InCl3-catalyzed, facile and efficient method for the synthesis of spirooxindoles under conventional and solvent-free microwave conditions[J].Tetrahedron,2007(9):2057-2063. |
| [11] | Gao S;Tsai C H;Tseng C;Yao C F .[J].Tetrahedron,2008,64:9143. |
| [12] | Sridhar R;Srinivas B;Madhav B;Reddy V P Nageswar Y V D Rao K R .[J].Canadian Journal of Chemistry,2009,87:1704. |
| [13] | Dabiri, M;Bahramnejad, M;Baghbanzadeh, M .Ammonium salt catalyzed multicomponent transformation: simple route to functionalized spirochromenes and spiroacridines[J].Tetrahedron,2009(45):9443-9447. |
| [14] | Zhu S-L;Ji S-J;Zhang Y .[J].Tetrahedron,2007,63:9365. |
| [15] | Hari G S;Lee Y R.[J].Synthesis,2010:453. |
| [16] | Tang T;Zhao Y;Xu Y;Wu D Xu J Deng F .[J].Applied Surface Science,2011,257:6004. |
| [17] | Yasmin, T.;Müller, K. .Synthesis and characterization of surface modified SBA-15 silica materials and their application in chromatography[J].Journal of chromatography, A: Including electrophoresis and other separation methods,2011(37):6464-6475. |
| [18] | Song SW;Hidajat K;Kawi S .Functionalized SBA-15 materials as carriers for controlled drug delivery: Influence of surface properties on matrix-drug interactions[J].Langmuir: The ACS Journal of Surfaces and Colloids,2005(21):9568-9575. |
| [19] | Ziarani G M;Badiei A R;Khaniania Y;Haddadpour M .[J].IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION,2010,29(02):1. |
| [20] | Chen S Y;Huang C Y;Yokoi T;Tang C Y Huang S J Lee J J Chan J C C Tatsumi T Cheng S .[J].Journal of Materials Chemistry,2012,22:2233. |
| [21] | Sujandi;Eko Adi Prasetyanto;Sang-Eon Park .Synthesis of short-channeled amino-functionalized SBA-15 and its beneficial applications in base-catalyzed reactions[J].Applied Catalysis, A. General: An International Journal Devoted to Catalytic Science and Its Applications,2008(2):244-251. |
| [22] | Shahbazi A;Younesi H;Badiei A .[J].Chemical Engineering Journal,2011,168:505. |
| [23] | Badiei A;Goldooz H;Ziarani G M .[J].Applied Surface Science,2011,257:4912. |
| [24] | Chong M A S;Zhao X S .[J].Journal of Physical Chemistry B,2003,107:12650. |
| [25] | Zhao D;Huo Q;Feng J;Chmelka B F Stucky G D .[J].Journal of the American Chemical Society,1998,120:6024. |
| [26] | Badiei, A.;Goldooz, H.;Ziarani, G.M.;Abbasi, A. .One pot synthesis of functionalized SBA~(-1)5 by using an 8-hydroxyquinoline-5-sulfonamide-modified organosilane as precursor[J].Journal of Colloid and Interface Science,2011(1):63-69. |
| [27] | Mohammadi Ziarani G;Badiei A;Hassanzadeh M;Mousavi S.[J].Arabian JChem,2012 |
| [28] | Mohammadi Ziarani G;Badiei A;Haddadpour M .[J].International Journal of Chemistry,2011,3(01):87. |
| [29] | Mohammadi Ziarani G;Badiei A;Shahjafari F;Pourjafar T .[J].South African Journal of Chemistry,2012,65:10. |
| [30] | Chai S-J;Lai Y-F;Xu J-C;Zheng H Zhu Q Zhang P-F .[J].Advanced Synthesis and Catalysis,2011,353:371. |
| [31] | Elinson M N;Ilovaisky A I;Dorofeev A S;Merkulova V M Stepanov N O Miloserdov F M Ogibin Y N Nikishin G I .[J].Tetrahedron,2007,63:10543. |
| [32] | Li Y;Chen H;Shi C;Shi D Ji S .[J].Journal of Combinatorial Chemistry,2010,12:231. |
| [33] | Singh Raghuvanshi D;Nand Singh K .[J].Journal of Heterocyclic Chemistry,2010,47:1323. |
| [34] | Shmidt M S;Reverdito A M;Kremenchuzky L;Perillo I A Blanco M M .[J].Molecules,2008,13:831. |
| [35] | Marti C;Carreira E M .[J].Journal of the American Chemical Society,2005,127:11505. |
| [36] | Majumdar K C;Kundu A K;Chatterjee P.[J].Journal of Chemical Research Synopsis,1996:460. |
| [37] | Ukrainets I V;Bereznyakova N L;Gorokhova O V;Shishkina S V .[J].Chemistry of Heterocyclic Compounds,2009,45:1241. |
| [38] | Shemchuk L A;Chernykh V P;Red’kin R G .[J].Russian Journal of Organic Chemistry,2008,44:1789. |
| [39] | Mortikov V Y;Litvinov Y M;Shestopalov A A;Rodinovskaya L A Shestopalov A M .[J].Russian Chemical Bulletin International Edition,2008,57:2373. |
| [40] | Wang, LM;Jiao, N;Qiu, J;Yu, JJ;Liu, JQ;Guo, FL;Liu, Y .Sodium stearate-catalyzed multicomponent reactions for efficient synthesis of spirooxindoles in aqueous micellar media[J].Tetrahedron,2010(1):339-343. |
| [41] | Mobinikhaledi, A.;Foroughifar, N.;Fard, M.A.B. .Simple and efficient method for three-component synthesis of spirooxindoles in aqueous and solvent-free media[J].Synthetic Communications,2011(1/3):441-450. |
| [42] | Zhao D;Feng J;Huo Q;Melosh N Fredrickson G H Chmelka B F Stucky G D .[J].Science,1998,279:548. |
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%