Green chemistry approaches to condensation reactions of formylferrocene with active methylene containing compounds

Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry

Volumn 34, Issue 8, 2004, Pages 1487-1496

  Bai, Yinjuan ^a   Lu, Jun ^a   Gan, Haiying ^a   Wang, Zhenjun ^a   Shi, Zhen ^a  

^a NORTHWEST UNIVERSITY   (China)

Author keywords

Active methylene; Formylferrocene; Green chemistry

Indexed keywords

CARBENE; FERROCENE DERIVATIVE; WATER;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; GRINDING; HEATING; INFRARED SPECTROMETRY; MICROWAVE IRRADIATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 6344249382     PISSN: 00945714     EISSN: None     Source Type: Journal    
DOI: 10.1081/SIM-200026298     Document Type: Article

References (31)

1. Clark, J.H. Green chemistry: challenges and opportunities. Green Chem. 1999, 1, 1-8.
2. Kaupp, G.; Reza Naimi-Jamal, M.; Schmeyers, J. Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield. Tetrahedron 2003, 59, 3753-3760.
3. Yoshizawa, K.; Toyota, S.; Toda, F. Solvent-free Claisen and Cannizzaro reactions. Tetrahedron Lett. 2001, 42, 7983-7985.
4. Liu, W.; Xu, Q.; Ma, Y.; Liang, Y.; Dong, N.; Guan, D. Solvent-free synthesis of ferrocenylethene derivatives. J. Organomet. Chem. 2001, 625, 128-131.
5. Kappe, C.O. High-speed combinatorial synthesis utilizing microwave irradiation. Curr. Opin. Chem. Biol. 2002, 6, 314-320.
6. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis - a review. Tetrahedron 2001, 57, 9225-9283.
7. Perreux, L.; Loupy, A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 2001, 57, 9199-9223.
8. Bigi, F.; Carloni, S.; Ferrari, L.; Maggi, R.; Mazzacani, A.; Sartori, G. Clean synthesis in water. Part 2. Uncatalysed condensation reaction of Meldrum's acid and aldehydes. Tetrahedron Lett. 2001, 42, 5203-5205.
9. Tanaka, K.; Shiraishi, R. Clean and efficient condensation reactions of aldehydes and amines in a water suspension medium. Green Chem. 2000, 2, 272-273.
10. Tsukinoki, T.; Kanda, T.; Liu, G.; Tsuzuki, H.; Tashiro, M. Organic reaction in water. Part 3. A facile method for reduction of aromatic rings using a Raney Ni-Al alloy in dilute aqueous alkaline solution under mild conditions. Tetrahedron Lett. 2000, 41, 5865-5868.
11. McCluskey, A.; Robinson, P.J.; Hill, T.; Scottc, J.L.; Edwards, J.K. Green chemistry approaches to the Knoevenagel condensation: comparison of ethanol, water and solvent-free (dry grind) approaches. Tetrahedron Lett. 2002, 43, 3117-3120.
12. Hudson, R.D.A. Ferrocene polymers: current architectures, syntheses and utility. J Organomet. Chem. 2001, 637-639, 47-69.
13. Li, M.; Bai, Y.; Lu, J.; Yang, B.; Zhu, K.; Ma, H. Ferrocene derivatives (I). Synthesis and x-ray structure determination of N-o-methylphenylferrocene sulfonamide. J. Organomet. Chem. 2001, 637-639, 738-741.
14. Fery-Forgues, S.; Delavaux-Nicot, B. Ferrocene and ferrocenyl derivatives in luminescent systems. J. Photochem. Photobiol. A Chem. 2000, 132, 137-159.
15. Wright, M.E.; Toplikar, E.G. Organometallic nonlinear optical polymers 2. Synthesis of main-chain organometallic polymers and structural study of ferrocene NLO-phores. Macromolecules 1992, 25, 6050-6054.
16. Zimmer-Galler, R. Ferrocene Derivatives Useful as Catalysts for Combustions of Composite Explosives. US 3,755,311, Aug. 28, 1973 (Chem. Abstr. 1974, 80, 5442g).
17. Furdik, M.; Eleeko, P.; Toma, S.; Suchy, J. Derivatives of ferrocene. I. The synthesis from acetylferrocene. Chem. Zvesti. 1960, 15, 501-512 (Chem. Abstr. 1961, 55, 16508d).
18. Furdik, M.; Eleeko, P.; Toma, S.; Suchy, J. Derivatives of ferrocene. I. The synthesis from acetylferrocene. Chem. Zvesti. 1960, 15, 501-512 (Chem. Abstr. 1961, 55, 16508d).
19. Toma, S. Derivatives of ferrocene. XII. Ferrocene analogs of chalcones. Chem. Zvesti. 1965, 19, 703-710 (Chem. Abstr. 1966, 64, 753f).
20. Toma, S. Derivatives of ferrocene. XII. Ferrocene analogs of chalcones. Chem. Zvesti. 1965, 19, 703-710 (Chem. Abstr. 1966, 64, 753f).
21. Toda, F.; Tanaka, K.; Hamai, K. Aldol condenstations in the absence of solvent: acceleration of the reaction and enhancement of the stereoselectivity. J. Chem. Soc. Perkin Trans. 1990, 3207-3209.
22. Villemin, D.; Martin, B.; Puciova, M.; Toma, S. Dry synthesis under microwave irradiation: synthesis of ferrocenylenones. J. Organomet. Chem. 1994, 484, 27-31.
23. Liu, W.; Xu, Q.; Chen, B.; Ma, Y. Solid-phase synthesis of ferrocenylchalkone. Synth. Commun. 2002, 32, 171-174.
24. Sato, M.; Kono, H.; Shiga, M.; Motoyama, I.; Hata, K. Simple modification of the Vilsmeier method for the preparation of formylferrocene. Bull. Chem. Soc. Japan 1968, 41, 252.
25. Graham, P.J.; Lindsey, R.V.; Parshall, G.W.; Peterson, M.L.; Whitman, G.M. Some acylferrocenes and their reactions. J. Am. Chem. Soc. 1957, 79 (13), 3416-3424.
26. Stankovic, E.; Toma, S.; Van Boxel, R.; Asselberghs, I.; Persoons, A. Knoevenagel condensation of ferrocenyl substituted carboxaldehydes with methylene active compounds on inorganic supports and the NLO properties of the resulting push-pull alkenes. J. Organomet. Chem. 2001, 637-639, 426-434.
27. Schuster, P.; Polansky, O.E.; Wessely, F.M. Cyclic acylals. VI. Monatsh. Chem. Abstr. 1964, 95, 53-58.
28. Hassan, K.M. Studies on ferrocene and its derivatives. IV. Some reactions with 1-phenyl-3-methyl-2-pyrazolin-5-one. J. Indian Chem. Soc. 1976, 53 (12), 1185-1189.
29. Barben, I.K. Some substituted ferrocenes. J. Chem. Soc. 1961, 1827-1828.
30. Villemin, D.; Labiad, B. Clay catalysis: dry condensation of 3-methyl-1-phenyl-5-pyrzaolone with aldehydes under microwave irradiation. Synth. Commun. 1990, 20, 3213-3218.
31. Klimova, E.I.; Garcia, M.M.; Berestneva, T.K.; Toledano, C.A.; Toskano, R.F.; Ramirez, L.R. The structure of bicyclic ferrocenylmethylene substituted 2-pyrazolines and their reactions with azodicarboxylic acid and N-phenylimide. J. Organomet. Chem. 1999, 585, 106-114.