A revision of the biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3465-3468

  Bigi, Franca ^a   Carloni, Silvia ^a   Frullanti, Bettina ^a   Maggi, Raimondo ^a   Sartori, Giovanni ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROPYRIDINE DERIVATIVE; MONTMORILLONITE; TOLUENE;

ALPHA ADRENERGIC RECEPTOR BLOCKING; ARTICLE; CALCIUM BINDING; CATALYSIS; ECONOMIC ASPECT; MOLECULAR DYNAMICS; PHASE TRANSITION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033597165     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00424-4     Document Type: Article

References (18)

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4. 3. Arienti, A.; Bigi, F.; Maggi, R.; Marzi, E.; Moggi, P.; Rastelli, M.; Sartori, G.; Tarantola, F. Tetrahedron,1997, 53, 3795; Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem, 1997, 62, 7024; Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Rastelli, M.; Sartori, G. Synthesis, 1998, 301; Bigi, F.; Maggi,R.; Sartori, G.; Zambonin, E. Chem. Commun., 1998, 513.
5. 3. Arienti, A.; Bigi, F.; Maggi, R.; Marzi, E.; Moggi, P.; Rastelli, M.; Sartori, G.; Tarantola, F. Tetrahedron,1997, 53, 3795; Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem, 1997, 62, 7024; Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Rastelli, M.; Sartori, G. Synthesis, 1998, 301; Bigi, F.; Maggi,R.; Sartori, G.; Zambonin, E. Chem. Commun., 1998, 513.
6. 3. Arienti, A.; Bigi, F.; Maggi, R.; Marzi, E.; Moggi, P.; Rastelli, M.; Sartori, G.; Tarantola, F. Tetrahedron,1997, 53, 3795; Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem, 1997, 62, 7024; Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Rastelli, M.; Sartori, G. Synthesis, 1998, 301; Bigi, F.; Maggi, R.; Sartori, G.; Zambonin, E. Chem. Commun., 1998, 513.
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13. 2O (1.5%).
14. 8. Vastly increased rates of the xonotlite-promoted Knoevenagel reaction in hydrocarbon and in water solution have been previously observed: Laszlo, P. Acc. Chem. Res., 1986, 19, 121.
15. 3: C, 60.0; H, 8.4; N, 11.7; found: C, 60.1; H, 8.5; N, 11.9.
16. 10. Aldehyde 1 (10 mmol), β-dicarbonyl compound 2 (10 mmol), urea 3 (0.9 g, 15 mmol) and montmorillonite KSF (0.5 g) were heated at 130°C under stirring for 48 hours. Hot methanol (100 ml) was added and the mixture was filtered to remove the catalyst. Products 4 crystallized after several hours and were recovered by filtration.
17. 11. Dömling, A.; Herdtweck, E.; Ugi, I. Acta Chem. Scand., 1998, 52, 107; Balogh, M.; Laszlo, P. "OrganicChemistry using Clays", Springer Verlag, New York, 1993, pp 155-165.
18. 11. Dömling, A.; Herdtweck, E.; Ugi, I. Acta Chem. Scand., 1998, 52, 107; Balogh, M.; Laszlo, P. "Organic Chemistry using Clays", Springer Verlag, New York, 1993, pp 155-165.