Reactions of amines with zwitterionic quinoneimines: synthesis of new anionic and zwitterionic quinonoids

European Journal of Organic Chemistry

Volumn , Issue 20, 2009, Pages 3340-3350

  Tamboura, Farba B ^a   Cazin, Catherine S J ^a,b   Pattacini, Roberto ^a   Braunstein, Pierre ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

Amination; C n activation; Hydrogen bonds; Quinones; Zwitterions

Indexed keywords

EID: 67650506908     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900154     Document Type: Article

References (60)

1. S. Patai, Z. Rappoport, The Chemistry of the Quinonoid Compounds, Wiley, New York, 1988, vols. 1 and 2.
2. J. F. Corbett, J. Soc. Cosmet. Chem. 1984, 35, 297.
3. Y Lee, L. M. Sayre, J. Am. Chem. Soc. 1995, 117, 3096.
4. R. H. Thomson, Naturally Occurring Quiñones, Blackie Academic and Professional, London, 1997.
5. A. B. P. Lever, S. I. Ciorelsky, Coord, Chem. Rev. 2000, 208, 153.
6. B. F. Abrahams, K. D. Lu, B. Moubaraki, K. S. Murray, R. Robson, J. Chem. Soc., Dalton Trans. 2000, 1793.
7. G. A. Abakumov, V. K. Cherkasov, V. I. Nevodchikov, V. A. Kuropatov, G. T. Yee, C. G. Pierpont, Inorg. Chem. 2001, 40, 2434.
8. P. Chaudhuri, C. N. Verani, E. Bill, E. Bothe, T. Weyhermüller, K. Wieghardt, J. Am. Chem. Soc. 2001, 123, 2213.
9. S. Hünig, C. A. Briehn, P. Bäuerle, A. Emge, Chem. Eur. J. 2001, 7, 2745.
10. T. Ling, E. Poupon, E. J. Rueden, S. H. Kim, E. A. Theodorakis, J. Am. Chem. Soc. 2002, 124, 12261.
11. P. Stahl, L. Kissau, R. Mazitschek, A. Giannis, H. Waldmann, Angew. Chem. 2002, 114, 1222;
12. Angew. Chem. Int. Ed. 2002, 41, 1174.
13. H.-L. Chan, H.-Q. Liu, B.-C. Tzeng, Y.-S. You, S.-M. Peng, M. Yang, C.-M. Che, Inorg. Chem. 2002, 41, 3161.
14. O. Siri, P. Braunstein, M.-M. Rohmer, M. Bénard, R. Welter, J. Am. Chem. Soc. 2003, 125, 13793.
15. M. Oh, G. B. Carpenter, D. A. Sweigart, Organometallics 2003, 22, 2364.
16. K. S. Min, T. Weyhermüller, K. Wieghardt, Dalton Trans. 2003, 1126.
17. M. Largeron, A. Neudorffer, M.-B. Fleury, Angew. Chem. Int. Ed. 2003, 42, 1026.
18. R. S. Coliman, F. X. Felpin, W. Chen, J. Org. Chem. 2004, 69, 7309.
19. H. Ohtsu, K. Tanaka, Angew. Chem. Int. Ed. 2004, 43, 6301.
20. M. Elhabiri, O. Siri, A. Sornosa-Tent, A.-M. Albrecht-Gary, P. Braunstein, Chem. Eur. J. 2004, 10, 134.
21. P. Braunstein, O. Siri, J.-P. Taquet, Q.-Z. Yang, Chem. Eur. J. 2004, 10, 3817.
22. P. Braunstein, A. Demessence, O. Siri, J.-P. Taquet, C. R. Chim. 2004, 7, 909.
23. S.-I. Noro, H.-C. Chang, T. Takenobu, Y. Murayama, T. Kanbara, T. Aoyama, T. Sassa, T. Wada, D. Tanaka, S. Kitagawa, Y. Iwasa, T. Akutagawa, T. Nakamura, J. Am. Chem. Soc. 2005, 127, 10012.
24. S. U. Son, S. B. Kim, J. A. Reingold, G. B. Carpenter, D. A. Sweigart, J. Am. Chem. Soc. 2005, 127, 12238.
25. S. Kar, B. Sarkar, S. Ghumaan, D. Janardanan, J. van Slageren, J. Fiedler, V. G. Puranik, R. B. Sunoj, W. Kaim, G. K. Lahiri, Chem. Eur. J. 2005, 11, 4901.
26. J.-P. Taquet, O. Siri, J.-P. Collin, A. Messaoudi, P. Braunstein, New J. Chem. 2005, 29, 188.
27. O. Siri, J.-P. Taquet, J.-P. Collin, M.-M. Rohmer, M. Bénard, P. Braunstein, Chem. Eur. J. 2005, 11, 7247.
28. H. Mustroph, M. Stollenwerk, V. Bressau, Angew. Chem. Int. Ed. 2006, 45, 2016.
29. S.-L. Kokatam, P. Chaudhuri, T. Weyhermüller, K. Wieghardt, Dalton Trans. 2007, 373.
30. O. Siri, P. Braunstein, J.-P. Taquet, J.-P. Collin, R. Welter, Dalton Trans. 2007, 1481.
31. S. M. Carter, A. Sia, M. J. Shaw, A. F. Heyduk, J. Am. Chem. Soc. 2008, 130, 5838.
32. B. Therrien, G. Süss-Fink, P. Govindaswamy, A. K. Renfrew, P. J. Dyson, Angew. Chem. Int. Ed. 2008, 47, 3773.
33. C. Seillan, P. Braunstein, O. Siri, Eur. J. Org. Chem. 2008, 3113.
34. Y.-B. Huang, G.-R. Tang, G.-Y Jin, G.-X. Jin, Organometallics 2008, 27, 259.
35. P. Braunstein, O. Siri, P. Steflanut, M. Winter, Q.-Z. Yang, C. R. Chim. 2006, 9, 1493.
36. P. Braunstein, O. Siri, J.-P. Taquet, Q.-Z. Yang, Angew. Chem. Int. Ed. 2006, 45, 1393.
37. O. Siri, P. Braunstein, Chem. Commun. 2002, 208.
38. M. Oh, G. B. Carpenter, D. A. Sweigart, Acc. Chem. Res. 2004, 37, 1.
39. P. Braunstein, O. Siri, J.-P. Taquet, M.-M. Rohmer, M. Bénard, R. Welter, J. Am. Chem. Soc. 2003, 125, 12246.
40. J.-p. Taquet, O. Siri, P. Braunstein, R. Welter, Inorg. Chem. 2004, 43, 6944.
41. Q.-Z. Yang, O. Siri, P. Braunstein, Chem. Eur. J. 2005, 11, 7237.
42. F. A. Cotton, J.-Y. Jin, Z. Li, C. A. Murillo, J. H. Reibenspies, Chem. Commun. 2008, 211.
43. A. I. Poddel'sky, V. K. Cherkasov, G. A. Abakumov, Coord. Chem. Rev. 2009, 253, 291.
44. J.-P. Taquet, O. Siri, P. Braunstein, Inorg. Chem. 2006, 45, 4668.
45. P. Braunstein, D. Bubrin, B. Sarkar, Inorg. Chem. 2009, 48, 2534.
46. Q.-Z. Yang, A. Kermagoret, M. Agostinho, O. Siri, P. Braunstein, Organometallics 2006, 25, 5518.
47. Q.-Z. Yang, O. Siri, P. Braunstein, Chem. Commun. 2005, 2660.
48. A. Sawicka, P. Skurski, J. Simons, Chem. Phys. Lett. 2002, 362, 527;
49. b) Delaere, P. C. Nam, M. T. Nguyen, Chem. Phys. Lett. 2003, 382, 349;
50. H. T. Le, P. C. Nam, V. L. Dao, T. Veszprémi, M. T. Nguyen, Mol. Phys. 2003, 101, 2437;
51. Y. Hass, S. Zilberg, J. Am., Chem., Soc. 2004, 126, 8991.
52. G. Meazza, B. E. Scheffler, M. R. Tellez, A. M. Rimando, J. G. Romagni, S. O. Duke, D. Nanayakkara, I. A. Khan, E. A. Abourashed, F. E. Dayan, Phytochemisty 2002, 59, 281;
53. h) Aguilar-Martinez, J. A. Bautista-Martinez, N. Macias-Ruvalcaba, I. Gonzàlez, E. Tovar, T. M. del Alizal, O. Collera, G. Cuevas, J. Org. Chem. 2001, 66, 8349;
54. i)N. U. Frigaard, S. Tokita, K. Matsuura, Biochim. Biophys. Acta 1999,1413, 108;
55. J) J. Inbaraj, R. Gandhidasan, R. Murugesan, Free Radical Biol. Med. 1999, 26, 1072;
56. k)N. R. Bachur, S. L. Gordon, M. V. Gee, Cancer Res. 1978, 38, 1745;
57. l)N Subbarayudu, Y D. Satyanarayana, E. Venkata-Rao, D. Venkata-Rao, Ind. J. Pharm. Sci. 1978, 173;
58. m)B. S. Joshi, V. N. Kamat, Ind. J. Chem 1975, 13, 795.
59. n)Bruker-Nonius, Kappa CCD Reference Manual, Nonius BV, The Netherlands, 1998.
60. o)G. M. Sheldrick, SHELXL-97: Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.