KG-60-piperazine as a new heterogeneous catalyst for gewald three-component reaction

Synthetic Communications

Volumn 43, Issue 13, 2013, Pages 1859-1864

  Rezaei Seresht, Esmail ^a   Tayebee, Reza ^a   Yasemi, Mohammad ^a  

^a HAKIM SABZEVARI UNIVERSITY   (Iran)

Author keywords

2 Aminothiophenes; Gewald reaction; heterogeneous catalysis; multicomponent reaction

Indexed keywords

ALDEHYDE; CARBONYL DERIVATIVE; KETONE; MALONONITRILE; PIPERAZINE DERIVATIVE; SILICON DIOXIDE;

ARTICLE; CATALYST; CHEMICAL REACTION; GEWALD THREE COMPONENT REACTION;

EID: 84876117018     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2012.674607     Document Type: Article

References (25)

1. Gewald, K.; Schinke, E.; Böttcher, H. Heterocyclen aus CH-aciden nitrilen, VIII: 2-Amino-thiophene aus methylenaktiven nitrilen, carbonylverbindungen und schwefel. Chem. Ber. 1966, 99, 94-100.
2. Gewald, K. Zur Reaktion von α-oxo-mercaptanen mit nitrilen. Angew. Chem. 1961, 73, 114.
3. Naumann, B.; Böhm, R.; Fülöp, F.; Bernáth, G. Preparation of new trifunctional thiophene derivatives. Pharmazie 1996, 51, 4-6.
4. Hallas, G.; Choi, J.-H. Synthesis and spectral properties of azo dyes derived from 2-aminothiophenes and 2-aminothiazoles. Dyes Pigm. 1999, 42, 249-265.
5. Sridhar, M.; Rao, R. M.; Baba, N. H. K.; Kumbhare, R. M. Microwave-accelerated Gewald reaction: Synthesis of 2-aminothiophenes. Tetrahedron Lett. 2007, 48, 3171-3172.
6. Hoener, A. P. F.; Henkel, B.; Gauvin, J.-C. Novel one-pot microwave-assisted Gewald synthesis of 2-acyl amino thiophenes on solid support. Synlett 2003, 63-66.
7. Huang, W.; Li, J.; Tang, J.; Liu, H., Shen, J.; Jiang, H. Microwave-assisted synthesis of 2-amino-thiophene-3-carboxylic derivatives under solvent-free conditions. Synth. Commun. 2005, 35, 1351-1357.
8. Mekheimer, R. A.; Ameen, M. A.; Sadek, K. U. Solar thermochemical reactions II: Synthesis of 2-aminothiophenes via Gewald reaction induced by solar thermal energy. Chin. Chem. Lett. 2008, 19, 788-790.
9. Hu, Y.; Chen, Z.-C.; Le, Z.-G.; Zheng, Q.-G. Organic reactions in ionic liquids: Gewald synthesis of 2-aminothiophenes catalyzed by ethylenediammonium diacetate. Synth. Commun. 2004, 34, 3801-3806.
10. Feroci, M.; Chiarotto, I.; Rossi, L.; Inesi, A. Activation of elemental sulfur by electrogenerated cyanomethyl anion: Synthesis of substituted 2-aminothiophenes by the Gewald reaction. Adv. Synth. Catal. 2008, 350, 2740-2746.
11. (a), Notestein, J. M.; Katz, A. Enhancing heterogeneous catalysis through cooperative hybrid organic-inorganic interfaces. Chem. Eur. J. 2006, 12, 3954-3965
12. (b), Tada, M.; Iwasawa, Y. Advanced chemical design with supported metal complexes for selective catalysis. Chem. Commun. 2006, 2833-2844
13. (c), Corma, A.; Garcia, H. Silica-bound homogenous catalysts as recoverable and reusable catalysts in organic synthesis. Adv. Synth. Catal. 2006, 348, 1391-1412
14. (d), Song, C. E.; Kim, D. H.; Choi, D. S. Chiral organometallic catalysts in confined nanospaces: Significantly enhanced enantioselectivity and stability. Eur. J. Inorg. Chem. 2006, 2927-2935
15. (e), Dioos, B. M. L.; Vankelecom, I. F. J.; Jacobs, P. A. Aspects of immobilisation of catalysts on polymeric supports. Adv. Synth. Catal. 2007, 348, 1413-1446.
16. Leznoff, C. C. The use of insoluble polymer supports in organic chemical synthesis. Chem. Soc. Rev. 1974, 3, 65-85.
17. Shimizu, K.-I.; Suzuki, H.; Hayashi, E.; Kodama, T.; Tsuchiya, Y.; Hagiwara, H.; Kitayama, Y. Catalytic direct 1,4-conjugate addition of aldehydes to vinylketones on secondary amines immobilised in FSM-16 silica. Chem. Commun. 2002, 1068-1069.
18. Angeletti, E.; Canepa, C.; Martinetti, G.; Venturello, P. Silica gel functionalized with amino groups as a new catalyst for Knoevenagel condensation under heterogeneous catalysis conditions. Tetrahedron Lett. 1988, 29, 2261-2264.
19. 2 in Michael and Henry reactions involving nitroalkanes. Tetrahedron Lett. 2003, 44, 2271-2273.
20. Motokura, K.; Tomita, M.; Tada, M.; Iwasawa, Y. Michael reactions catalyzed by basic alkylamines and dialkylaminopyridine immobilized on acidic silica-alumina surfaces. Top. Catal. 2009, 52, 579-585.
21. Puterová Z.; Krutošíková A.; Végh, D. Gewald reaction: Synthesis, properties, and applications of substituted 2-aminothiophenes. Arkivoc 2010, 1, 209-246.
22. Espinola, J. G. P.; Arakaki, L. N. H.; de Oliveira, S. F.; da Fonseca, M. G.; Filho, J. A. A. C.; Airoldi, C. Some thermodynamic data of the energetics of the interaction cation-piperazine immobilized on silica gel. Colloids Surf. A 2003, 221, 101-108.
23. Gewald, K. Heterocyclen aus CH-aciden nitrilen, VII: 2-Aminothiophene aus α-oxo-mercaptanen und methylenaktiven nitrilen. Chem. Ber. 1965, 98, 3571-3577.
24. Foye, W. O.; Mickles, J.; Boyce, G. M. Antiradiation compounds, XIV: Dithiocarbamates of aminothiophenes. J. Pharm. Sci. 1970, 59, 1348-1350.
25. Manhas, M. S.; Rao, V. V.; Setheraman, P. A.; Succardi, D.; Pazdera, J. Synthesis of thieno-and furo-pyrimidinethiones. J. Chem. Soc. C 1969, 1937-1939.