Microwave enhanced synthesis of acridines. A new aspect in the Bernthsen reaction

Green Chemistry

Volumn 4, Issue 4, 2002, Pages 390-391

  Seijas, Julio A ^a   Vázquez Tato, M Pilar ^a   Martínez, M Montserrat ^a   Rodríguez Parga, Jacobo ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 57249116824     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b204243f     Document Type: Article

References (26)

1. Acridines. The Chemistry of Heterocyclic Compounds, ed. R. M. Acheson, Interscience Publishers Inc., New York, 1956.
2. A. W. McConnanghis and T. C. Jenkins, J. Med. Chem., 1995, 38, 3488-3501; A. Lorente, M. Fernández Saiz and J. F. Espinosa, Tetrahedron Lett., 1995, 36, 5261-5264; M. Lourdan, J. García and J. Lhommen, Biochemistry, 1999, 38, 14205-213; S. Bonse, C. Santelli-Rouvier, J. Barbe and R. L. Krauth-Siegel, J. Med. Chem., 1999, 42, 5448-5454; S. A. Gamage, J. A. Spicer, G. J. Atwell, G. J. Finlay, B. C. Baguley and W. A. Denny, J. Med. Chem., 1999, 42, 2383-2393; J. Lhomme, J. Med. Chem., 1997, 40, 3346-3352; W. A. Denny, J. Med. Chem., 1996, 39, 2508-2517; S. R. Kirk, N. W. Luedtke and Y. Tor, J. Am. Chem. Soc., 2000, 122, 980-981.
3. A. W. McConnanghis and T. C. Jenkins, J. Med. Chem., 1995, 38, 3488-3501; A. Lorente, M. Fernández Saiz and J. F. Espinosa, Tetrahedron Lett., 1995, 36, 5261-5264; M. Lourdan, J. García and J. Lhommen, Biochemistry, 1999, 38, 14205-213; S. Bonse, C. Santelli-Rouvier, J. Barbe and R. L. Krauth-Siegel, J. Med. Chem., 1999, 42, 5448-5454; S. A. Gamage, J. A. Spicer, G. J. Atwell, G. J. Finlay, B. C. Baguley and W. A. Denny, J. Med. Chem., 1999, 42, 2383-2393; J. Lhomme, J. Med. Chem., 1997, 40, 3346-3352; W. A. Denny, J. Med. Chem., 1996, 39, 2508-2517; S. R. Kirk, N. W. Luedtke and Y. Tor, J. Am. Chem. Soc., 2000, 122, 980-981.
4. A. W. McConnanghis and T. C. Jenkins, J. Med. Chem., 1995, 38, 3488-3501; A. Lorente, M. Fernández Saiz and J. F. Espinosa, Tetrahedron Lett., 1995, 36, 5261-5264; M. Lourdan, J. García and J. Lhommen, Biochemistry, 1999, 38, 14205-213; S. Bonse, C. Santelli-Rouvier, J. Barbe and R. L. Krauth-Siegel, J. Med. Chem., 1999, 42, 5448-5454; S. A. Gamage, J. A. Spicer, G. J. Atwell, G. J. Finlay, B. C. Baguley and W. A. Denny, J. Med. Chem., 1999, 42, 2383-2393; J. Lhomme, J. Med. Chem., 1997, 40, 3346-3352; W. A. Denny, J. Med. Chem., 1996, 39, 2508-2517; S. R. Kirk, N. W. Luedtke and Y. Tor, J. Am. Chem. Soc., 2000, 122, 980-981.
5. A. W. McConnanghis and T. C. Jenkins, J. Med. Chem., 1995, 38, 3488-3501; A. Lorente, M. Fernández Saiz and J. F. Espinosa, Tetrahedron Lett., 1995, 36, 5261-5264; M. Lourdan, J. García and J. Lhommen, Biochemistry, 1999, 38, 14205-213; S. Bonse, C. Santelli-Rouvier, J. Barbe and R. L. Krauth-Siegel, J. Med. Chem., 1999, 42, 5448-5454; S. A. Gamage, J. A. Spicer, G. J. Atwell, G. J. Finlay, B. C. Baguley and W. A. Denny, J. Med. Chem., 1999, 42, 2383-2393; J. Lhomme, J. Med. Chem., 1997, 40, 3346-3352; W. A. Denny, J. Med. Chem., 1996, 39, 2508-2517; S. R. Kirk, N. W. Luedtke and Y. Tor, J. Am. Chem. Soc., 2000, 122, 980-981.
6. A. W. McConnanghis and T. C. Jenkins, J. Med. Chem., 1995, 38, 3488-3501; A. Lorente, M. Fernández Saiz and J. F. Espinosa, Tetrahedron Lett., 1995, 36, 5261-5264; M. Lourdan, J. García and J. Lhommen, Biochemistry, 1999, 38, 14205-213; S. Bonse, C. Santelli-Rouvier, J. Barbe and R. L. Krauth-Siegel, J. Med. Chem., 1999, 42, 5448-5454; S. A. Gamage, J. A. Spicer, G. J. Atwell, G. J. Finlay, B. C. Baguley and W. A. Denny, J. Med. Chem., 1999, 42, 2383-2393; J. Lhomme, J. Med. Chem., 1997, 40, 3346-3352; W. A. Denny, J. Med. Chem., 1996, 39, 2508-2517; S. R. Kirk, N. W. Luedtke and Y. Tor, J. Am. Chem. Soc., 2000, 122, 980-981.
7. A. W. McConnanghis and T. C. Jenkins, J. Med. Chem., 1995, 38, 3488-3501; A. Lorente, M. Fernández Saiz and J. F. Espinosa, Tetrahedron Lett., 1995, 36, 5261-5264; M. Lourdan, J. García and J. Lhommen, Biochemistry, 1999, 38, 14205-213; S. Bonse, C. Santelli-Rouvier, J. Barbe and R. L. Krauth-Siegel, J. Med. Chem., 1999, 42, 5448-5454; S. A. Gamage, J. A. Spicer, G. J. Atwell, G. J. Finlay, B. C. Baguley and W. A. Denny, J. Med. Chem., 1999, 42, 2383-2393; J. Lhomme, J. Med. Chem., 1997, 40, 3346-3352; W. A. Denny, J. Med. Chem., 1996, 39, 2508-2517; S. R. Kirk, N. W. Luedtke and Y. Tor, J. Am. Chem. Soc., 2000, 122, 980-981.
8. A. W. McConnanghis and T. C. Jenkins, J. Med. Chem., 1995, 38, 3488-3501; A. Lorente, M. Fernández Saiz and J. F. Espinosa, Tetrahedron Lett., 1995, 36, 5261-5264; M. Lourdan, J. García and J. Lhommen, Biochemistry, 1999, 38, 14205-213; S. Bonse, C. Santelli-Rouvier, J. Barbe and R. L. Krauth-Siegel, J. Med. Chem., 1999, 42, 5448-5454; S. A. Gamage, J. A. Spicer, G. J. Atwell, G. J. Finlay, B. C. Baguley and W. A. Denny, J. Med. Chem., 1999, 42, 2383-2393; J. Lhomme, J. Med. Chem., 1997, 40, 3346-3352; W. A. Denny, J. Med. Chem., 1996, 39, 2508-2517; S. R. Kirk, N. W. Luedtke and Y. Tor, J. Am. Chem. Soc., 2000, 122, 980-981.
9. A. W. McConnanghis and T. C. Jenkins, J. Med. Chem., 1995, 38, 3488-3501; A. Lorente, M. Fernández Saiz and J. F. Espinosa, Tetrahedron Lett., 1995, 36, 5261-5264; M. Lourdan, J. García and J. Lhommen, Biochemistry, 1999, 38, 14205-213; S. Bonse, C. Santelli-Rouvier, J. Barbe and R. L. Krauth-Siegel, J. Med. Chem., 1999, 42, 5448-5454; S. A. Gamage, J. A. Spicer, G. J. Atwell, G. J. Finlay, B. C. Baguley and W. A. Denny, J. Med. Chem., 1999, 42, 2383-2393; J. Lhomme, J. Med. Chem., 1997, 40, 3346-3352; W. A. Denny, J. Med. Chem., 1996, 39, 2508-2517; S. R. Kirk, N. W. Luedtke and Y. Tor, J. Am. Chem. Soc., 2000, 122, 980-981.
10. A. Bernthsen, Justus Liebig's Ann. Chem., 1884, 224, 1.
11. M. P. Vázquez-Tato, Synlett, 1993, 506; J. A. Seijas, M. P. Vázquez-Tato, M. M. Martínez and G. Núñez-Corredoira, J. Chem. Res. (S), 1999, 420-421; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Tetrahedron Lett., 2000, 41, 2215-2217; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Spanish Pat. Appl., P200002113, 22 August 2000; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Synthesis, 2001, 999-1000; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Synlett, 2001, 875-877.
12. M. P. Vázquez-Tato, Synlett, 1993, 506; J. A. Seijas, M. P. Vázquez-Tato, M. M. Martínez and G. Núñez-Corredoira, J. Chem. Res. (S), 1999, 420-421; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Tetrahedron Lett., 2000, 41, 2215-2217; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Spanish Pat. Appl., P200002113, 22 August 2000; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Synthesis, 2001, 999-1000; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Synlett, 2001, 875-877.
13. M. P. Vázquez-Tato, Synlett, 1993, 506; J. A. Seijas, M. P. Vázquez-Tato, M. M. Martínez and G. Núñez-Corredoira, J. Chem. Res. (S), 1999, 420-421; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Tetrahedron Lett., 2000, 41, 2215-2217; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Spanish Pat. Appl., P200002113, 22 August 2000; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Synthesis, 2001, 999-1000; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Synlett, 2001, 875-877.
14. M. P. Vázquez-Tato, Synlett, 1993, 506; J. A. Seijas, M. P. Vázquez-Tato, M. M. Martínez and G. Núñez-Corredoira, J. Chem. Res. (S), 1999, 420-421; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Tetrahedron Lett., 2000, 41, 2215-2217; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Spanish Pat. Appl., P200002113, 22 August 2000; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Synthesis, 2001, 999-1000; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Synlett, 2001, 875-877.
15. M. P. Vázquez-Tato, Synlett, 1993, 506; J. A. Seijas, M. P. Vázquez-Tato, M. M. Martínez and G. Núñez-Corredoira, J. Chem. Res. (S), 1999, 420-421; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Tetrahedron Lett., 2000, 41, 2215-2217; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Spanish Pat. Appl., P200002113, 22 August 2000; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Synthesis, 2001, 999-1000; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Synlett, 2001, 875-877.
16. M. P. Vázquez-Tato, Synlett, 1993, 506; J. A. Seijas, M. P. Vázquez-Tato, M. M. Martínez and G. Núñez-Corredoira, J. Chem. Res. (S), 1999, 420-421; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Tetrahedron Lett., 2000, 41, 2215-2217; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Spanish Pat. Appl., P200002113, 22 August 2000; J. A. Seijas, M. P. Vázquez-Tato, C. González-Bande and B. Pacios-López, Synthesis, 2001, 999-1000; J. A. Seijas, M. P. Vázquez-Tato and M. M. Martínez, Synlett, 2001, 875-877.
17. Domestic microwave ovens are suitable for many microwave enhanced reactions, since most of them are performed in absence of solvent and non-flammable reagents are used. For a discussion on this subjet by researchers on this field, see the discussion list on the last ECSOC-5 Symposium on Microwave Assisted Synthesis (http://www.mdpi.net/ecsoc-5/).
18. J. A. Seijas, M. P. Vázquez-Tato, M. M. Martínez and J. Rodríguez-Parga, Chem. Abstr., 2001, 135, 46075; Communication a0068, Fourth Electronic Conference on Synthetic Organic Chemistry (ECSOC-4), September 2000. (http://www.unibas.ch/ecsoc-4/a0068/a0068.htm).
19. J. A. Seijas, M. P. Vázquez-Tato, M. M. Martínez and J. Rodríguez-Parga, Chem. Abstr., 2001, 135, 46075; Communication a0068, Fourth Electronic Conference on Synthetic Organic Chemistry (ECSOC-4), September 2000. (http://www.unibas.ch/ecsoc-4/a0068/a0068.htm).
20. Zinc chloride performance in the reaction is improved when purified by recrystallysation from dioxane: Purification of Laboratory Chemicals, ed. D. D. Perrin and W. L. F. Armarego, Pergamon Press, Oxford, UK, 3rd edn, 1988.
21. Buu-Hoï and J. Lecocq, Compt. Rend., 1944, 218, 794-794.
22. A. Schmid and H. Decker, Ber. Dtsch. Chem. Ges., 1906, 39, 933-939.
23. G. Jones II, M. S. Farahat, S. R. Greenfield, D. J. Gosztola and M. R. Wasielewski, Chem. Phys. Lett., 1994, 224, 40-46; M. S. Farahat, Ph. D. Dissertation, Boston University, 1993.
24. G. Jones II, M. S. Farahat, S. R. Greenfield, D. J. Gosztola and M. R. Wasielewski, Chem. Phys. Lett., 1994, 224, 40-46; M. S. Farahat, Ph. D. Dissertation, Boston University, 1993.
25. Buu-Hoï and J. Lecocq, Recl. Trav. Chim. Pays Bas, 1945, 64, 250-253.
26. E. Veverkova, M. Noskova and S. Toma, Synth. Commun., 2002, 32, 729-773.