Anionic access to silylated and germylated binuclear heterocycles

Chemistry - A European Journal

Volumn 20, Issue 32, 2014, Pages 10131-10139

  Boddaert, Thomas ^a,c   François, Cyril ^a   Mistico, Laetitia ^a   Querolle, Olivier ^b   Meerpoel, Lieven ^b   Angibaud, Patrick ^b   Durandetti, Muriel ^a   Maddaluno, Jacques ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

^c UNIVERSITÉ PARIS SUD   (France)

Author keywords

cyclization; heterocycles; lithium; reaction mechanisms; rearrangement

Indexed keywords

ANIONIC POLYMERIZATION; CHLORINE; LITHIUM; SILICON;

ELECTRON-RICH; HETEROCYCLES; REACTION MECHANISM; REARRANGEMENT;

CYCLIZATION;

EID: 84940245195     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201402597     Document Type: Article

References (40)

1. O. F. Guner, J. P. Bowen, Curr. Opin. Drug. Discovery Dev. 2013, 13, 1327-1342.
2. For a general review on bioisostere in drug design, see:, N. A. Meanwell, J. Med. Chem. 2011, 54, 2529-2591.
3. For reviews in more specific C/Si isosterism, see: a) W. Bains, R. Tacke, Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543
4. J. S. Mills, G. A. Showell, Expert Opin. Invest. Drugs 2004, 13, 1149-1157
5. A. K. Franz, Curr. Opin. Drug Discovery Dev. 2007, 10, 654-671.
6. For a review on organosilicon molecules with medicinal applications, see:, A. K. Franz, S. O. Wilson, J. Med. Chem. 2013, 56, 388-405.
7. For a review on C/Si switch in odorant design, see:, R. Tacke, S. Metz, Chem. Biodiversity 2008, 5, 920-941.
8. For a review on C/Si/Ge switch in medicinal chemistry, see:, R. Tacke, T. Heinrich, T. Kornek, M. Merget, S. A. Wagner, J. Gross, C. Keim, G. Lambrecht, E. Mutschler, T. Beckers, M. Bernd, T. Reissmann, Phosphorus Sulfur Silicon Relat. Elem. 1999, 150-151, 69-87.
9. For a recent example in medicinal chemistry, see:, S. Fujii, Y. Miyajima, H. Masuno, H. Kagechika, J. Med. Chem. 2013, 56, 160-166.
10. For examples in the design of odorants and fungicides, respectively, see:a) R. Tacke, B. Becker, D. Berg, W. Brandes, S. Dutzmann, K. Schaller, J. Organomet. Chem. 1992, 438, 45-55
11. R. Tacke, T. Schmid, C. Burschka, M. Penka, H. Surburg, Organometallics 2002, 21, 113-120.
12. G. A. Showell, M. J. Barnes, J. O. Daiss, J. S. Mills, J. G. Montana, R. Tacke, J. B. H. Warneck, Bioorg. Med. Chem. Lett. 2006, 16, 2555-2558.
13. R. Tacke, T. Kornek, T. Heinrich, C. Burschka, M. Penka, M. Pülm, C. Keim, E. Mutschler, G. Lambrecht, J. Organomet. Chem. 2001, 640, 140-165
14. R. Tacke, V. I. Handmann, K. Kreutzmann, C. Keim, E. Mutschler, G. Lambrecht, Organometallics 2002, 21, 3727-3752.
15. R. Tacke, T. Heinrich, R. Bertermann, C. Burscka, A. Hamacher, M. U. Kassack, Organometallics 2004, 23, 4468-4477
16. R. Tacke, F. Popp, B. Müller, B. Theis, C. Burschka, A. Hamacher, M. U. Kassack, D. Schepmann, B. Wünsch, U. Jurva, E. Wellner, ChemMedChem 2008, 3, 152-164
17. T. Johansson, L. Weidolf, F. Popp, R. Tacke, U. Jurva, Drug Metabolism and Disposition 2010, 38, 73-83.
18. S. Dörrich, J. B. Bauer, S. Lorenzen, C. Mahler, S. Schweeberg, C. Burschka, J. A. Baus, R. Tacke, P. Kraft, Chem. Eur. J. 2013, 19, 11396-11408
19. B. Förster, R. Bertermann, P. Kraft, R. Tacke, Organometallics 2014, 33, 338-346.
20. For recent and important examples, see:a) C. Blaszykowski, C. Brancour, A. L. Dhimane, L. Fensterbank, M. Malacria, Eur. J. Org. Chem. 2009, 1674-1678
21. S. Furukawa, J. Kobayashi, T. Kawashima, J. Am. Chem. Soc. 2009, 131, 14192-14193
22. S. V. Kirpichenko, A. I. Albanov, J. Organomet. Chem. 2010, 695, 663-666
23. K. Ouyang, Y. Liang, Z. Xi, Org. Lett. 2012, 14, 4572-4575
24. G. K. Min, D. Hernández, T. Skrydstrup, Acc. Chem. Res. 2013, 46, 457-470 and references cited therein
25. A. Giros, R. Guillot, L. Blanco, S. Deloisy, Eur. J. Org. Chem. 2013, 5809-5813.
26. C. François, T. Boddaert, M. Durandetti, O. Querolle, L. Van Hijfte, L. Meerpoel, P. Angibaud, J. Maddaluno, Org. Lett. 2012, 14, 2074-2077.
27. W. F. Bailey, S. C. Longstaff, Chimica Oggi (Chem. Today) 2001, 19, 28-32
28. J. Clayden, in Organolithiums: Selectivity for Synthesis, Pergamon Press, Oxford, 2002, pp. 111-142.
29. V. I. Handmann, R. Bertermann, C. Burschka, R. Tacke, J. Organomet. Chem. 2000, 613, 19-25
30. M. Shimizu, M. Iwakubo, Y. Nishihara, K. Oda, T. Hiyama, ARKIVOC (Gainesville, FL, U.S.) 2007, 29-48.
31. E. P. A. Couzijn, A. W. Ehlers, M. Schakel, K. Lammertsma, J. Am. Chem. Soc. 2006, 128, 13634-13639.
32. R. Damrauer, V. E. Yost, S. E. Danahey, B. K. O'Connell, Organometallics 1985, 4, 1779-1784
33. M. J. Allen, S. L. Aprahamian, E. A. Sans, H. Shechter, J. Org. Chem. 2002, 67, 3561-3574.
34. S. Berry, J. Chem. Phys. 1960, 32, 933-938
35. E. P. A. Couzijn, J. C. Slootweg, A. W. Ehlers, K. Lammertsma, J. Am. Chem. Soc. 2010, 132, 18127-18140
36. C. Moberg, Angew. Chem. 2011, 123, 10473-10475
37. Angew. Chem. Int. Ed. 2011, 50, 10290-10292.
38. N. V. Timosheva, T. K. Prakasha, A. Chandrasekaran, R. O. Day, R. R. Holmes, Inorg. Chem. 1995, 34, 4525-4526.
39. It is anyway unlikely that the two phenyls end up within the equatorial plane since the repulsive overlap between the aromatic π-systems is expected to destabilize this isomer:, E. P. A. Couzijn, D. W. F. van den Engel, J. C. Slootweg, F. J. J. de Kanter, A. W. Ehlers, M. Schakel, K. Lammertsma, J. Am. Chem. Soc. 2009, 131, 3741-3751.
40. We thank one of the referees for eliciting this discussion.