Synthesis of annulated pyridines by intramolecular inverse-electron-demand hetero-diels-alder reaction under superheated continuous flow conditions

European Journal of Organic Chemistry

Volumn , Issue 1, 2012, Pages 47-52

  Martin, Rainer E ^a   Morawitz, Falk ^a   Kuratli, Christoph ^a   Alker, André M ^b   Alanine, Alexander I ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

Cycloaddition; Flow chemistry; Nitrogen heterocycles; Superheated solvents

Indexed keywords

EID: 84055193467     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201101538     Document Type: Article

References (33)

1. T. Illg, P. Löb, V. Hessel, Bioorg. Med. Chem. 2010, 18, 3707-3719.
2. V. Hessel, Chem. Eng. Technol. 2009, 32, 1655-1681.
3. C. Wiles, P. Watts, Future Med. Chem. 2009, 1, 1593-1612.
4. F. Paviou, Pharm. Technol. Eur. 2009, 21, 22-32.
5. B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Chem. Rev. 2007, 107, 2300-2318.
6. C. Wiles, P. Watts, Chem. Commun. 2011, 47, 6512-6535.
7. P. Watts, C. Wiles (Eds.), Micro Reaction Technology in Organic Synthesis, CRC Press, Boca Raton, 2011.
8. T. Wirth (Ed.), Microreactors in Organic Synthesis and Catalysis, Wiley-VCH, Weinheim, 2008.
9. S. Ceylan, A. Kirschning, "Organic Synthesis in Mini Flow Reactors Using Immobilized Catalysts" in Recoverable and Recyclable Catalysts (Ed.:, M. Benaglia), John Wiley & Sons, New York, 2009, pp. 379-410.
10. V. Hessel, C. Knobloch, H. Löwe, Recent Pat. Chem. Eng. 2008, 1, 1-16.
11. A. Polyzos, M. O'Brien, T. P. Petersen, I. R. Baxendale, S. V. Ley, Angew. Chem. Int. Ed. 2011, 50, 1190-1193.
12. M. O'Brien, I. R. Baxendale, S. V. Ley, Org. Lett. 2010, 12, 1596-1598.
13. B. Gutmann, J.-P. Roduit, D. Roberge, C. O. Kappe, Angew. Chem. Int. Ed. 2010, 49, 7101-7105.
14. J. C. Brandt, S. C. Elmore, R. I. Robinson, T. Wirth, Synlett 2010, 20, 3099-3103.
15. A. A. Kulkami, V. S. Kalyani, R. A. Joshi, R. R. Joshi, Org. Process Res. Dev. 2009, 13, 999-1002.
16. A. E. Frissen, A. T. M. Marcelis, G. Geurtsen, D. A. de Brie, H. C. van der Plas, Tetrahedron 1989, 45, 5151-5162.
17. J. A. Joule, K. Mills, Heterocyclic Chemistry, 4th ed., Blackwell Science, Oxford, 2000, pp. 63-120.
18. K. Kral, M. Hapke, Angew. Chem. Int. Ed. 2011, 50, 2434-2435.
19. M. D. Hill, Chem. Eur. J. 2010, 16, 12052-12062.
20. A. E. Frissen, A. T. M. Marcelis, H. C. van der Plas, Tetrahedron 1989, 45, 803-812.
21. W. A. W. Stolle, A. T. M. Marcelis, A. Koetsier, H. C. van der Plas, Tetrahedron 1989, 45, 6511-6520.
22. D. M. Vandenberghe, G. J. Hoornaert, Bull. Soc. Chim. Belg. 1994, 103, 185-186.
23. T. Koike, Y. Hoashi, T. Takai, O. Uchikawa, Tetrahedron Lett. 2011, 52, 3009-3011.
24. D. L. Boger, S. M. Weinreb, "Hetero Diels-Alder Methodology in Organic Synthesis" in Organic Chemistry (Ed.:, H. H. Wasserman), Academic Press, New York, 1987.
25. W. A. W. Stolle, A. E. Frissen, A. T. M. Marcelis, H. C. van der Plas, Y. Wang, L. Häming, C. H. Stam, J. Org. Chem. 1991, 56, 2411-2416.
26. K. A. Brameld, B. Kuhn, D. C. Reuter, M. Stahl, J. Chem. Inf. Model. 2008, 48, 1-24.
27. I. Mamajanov, J. Herzfeld, J. Chem. Phys. 2009, 130, 134503/1-134503/6.
28. I. Mamajanov, J. Herzfeld, J. Chem. Phys. 2009, 130, 134504/1-134504/5.
29. C. N. Matthews, R. D. Minard, Faraday Discuss. 2006, 133, 393-401.
30. C. N. Matthews, Cell. Origin Life Extreme Habitats Astrobiol. 2004, 6, 121-135.
31. A. E. Frissen, A. T. M. Marcelis, H. C. van der Plas, Tetrahedron Lett. 1987, 28, 1589-1592.
32. -1). Based on a temperature difference between room temperature (23 °C) and reaction temperature (310 °C) of 289 K a volume expansion of 31 % is calculated. However, it should be noted that the thermal expansion coefficient α is only valid within a certain temperature range, as the volume expansion as a function of temperature is not strictly linear.
33. U. Tilstam, T. Defrance, T. Girard, Org. Process Res. Dev. 2009, 13, 321-323.