First synthesis of biquinolizinium salts: Novel example of a chiral azonia dication

Organic Letters

Volumn 8, Issue 26, 2006, Pages 5955-5958

  García Cuadrado, Domingo ^a   Cuadro, Ana M ^a   Alvarez Builla, Julio ^a   Sancho, Unai ^a   Castaño, Obis ^a   Vaquero, Juan J ^a  

^a UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INORGANIC SALT; PALLADIUM; QUINAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MODELS, MOLECULAR; PALLADIUM; QUINAZOLINES; SALTS; STEREOISOMERISM;

EID: 33846121581     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062314i     Document Type: Article

References (39)

1. Bringmann, G.; Ochse, M.; Schupp, O.; Tasler, S. In Progress in the Chemistry of Organic Natural Products; Springer: Wien, 2001; Vol. 82.
2. (a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
3. (b) Wang, G. T.; Wang, S.; Gentles, R.; Sowin, T.; Leitza, S.; Reilly, E. B.; von Geldern, T. W. Bioorg. Med, Chem. Lett. 2005, 15, 195.
4. (a) Yamamoto, T.; Maruyama, T.; Zhou, Z.; Ito, T.; Fukada, T.; Yoneda, Y.; Begum, F.; Ikeda, T.; Sasaki, S.; Takezoe, H.; Fukada, A.; Kubota, K. J. Am. Chem. Soc. 1994, 116, 4832.
5. (b) Schulz, E.; Fahmi, K.; Lemaire, M. Acros Org. Acta 1995, 1, 10.
6. (c) Zhu, S. S.; Swager, T. M. Adv. Mater. 1996, 8, 497.
7. (d) Papillon, J.; Schulz, E.; Gelinas, S.; Lessard, J.; Lemaire, M. Synth. Met. 1998, 96, 155.
8. Manka, J. T.; Guo, F.; Huang, J.; Yin, H.; Farrar, J. M.; Sienkowska, M.; Benin, V.; Kaszynski, P. J. Org. Chem. 2003, 68, 9574.
9. Supramol. Chem., 1st ed.; Lehn, J. M., Ed.; VCH: Weinheim, Germany, 1995.
10. For the use of BINAP ligands, see the Nobel lecture: Asymmetric catalysis: Science and opportunities. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
11. (a) The Viologens; Monk, P. S. M., Ed.; John Wiley: Canada, 1999.
12. (b) Stoddart, J. F. J. Am. Chem. Soc. 2000, 122, 164.
13. (c) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348.
14. (d) Stoddart, J. F. Acc. Chem. Res. 2001, 34, 410.
15. (e) Benniston, A. C.; Harriman, A.; Li, P.; Rostron, J. P. Tetrahedron Lett. 2005, 46, 7291.
16. (f) Branowska, D.; Rykowski, A.; Wysocki, Tetrahedron Lett. 2005, 46, 6223.
17. (g) Coe, B. J.; Harris, B. J.; Brunschwig, J. A.; Garin, B. S. W.; J.; Orduña, J. J. Am. Chem. Soc. 2005, 127, 3284.
18. (h) Dichtel, W. R.; Miljanic, O. S.; Spruell, J. M.; Heath, J. R.; Stoddart, J. F. J. Am. Chem. Soc. 2006, 128, 10388.
19. (i) Badjic, J. D.; Ronconi, C. M.; Stoddart, J. F.; Balzani, V.; Silvi, S.; Credi, A. J. Am. Chem. Soc. 2006, 128, 1489.
20. For the most recent review, see: Ihmels, H. Quinolizinium Salts and Benzo Analogues in Science of Synthesis; Black, D., Ed.; Georg Thieme Verlag: Stuttgart, 2004; Vol. 15, pp 907-946.
21. Boekelheide, V.; Gall, W. G. J. Am. Chem. Soc. 1954, 76, 1832.
22. For the only precedent of a bibenzoquinolizinium, see: Bradsher, C. K.; Yarrington, N. L. J. Org. Chem. 1963, 28, 78.
23. (a) Ullmann, F.; Bielecki, J. Chem. Ber. 1901, 34, 2174.
24. (b) Li, J. H.; Xie, Y. X.; Yin, D. L. J. Org. Chem. 2003, 68, 9867 and references therein.
25. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
26. (b) Negishi, E. Acc. Chem. Res. 1982, 15, 340.
27. (c) Farina, V. Pure Appl. Chem. 1996, 68, 73.
28. (d) Percec, V.; Bae, J.-Y.; M., Zhao, M.; Hill, D. H. J. Org. Chem. 1995, 60, 176.
29. (e) Stanforth, S. P. Tetrahedron 1998, 54, 263.
30. (a) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
31. (b) Nising, C. F.; Schmid, U. K.; Nieger, M.; Bräse, S. J. Org. Chem. 2004, 69, 6830.
32. (c) Demir, A. S.; Reis, O.; Emrullahoglu, M. J. Org. Chem. 2003, 68, 10130.
33. (d) Abiraj, K.; Srinivasa, G. R.; Channe Gowda, D. Tetrahedron Lett. 2004, 45, 2081.
34. (e) Li, J.-H.; Xie, Y.-K; Yin, D.-L J. Org. Chem. 2003, 68, 9867.
35. (f) Bringmann, G.; Price, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.
36. (a) Sanders, G. M.; van Dijk, M.; van der Plas, H. C. Heterocycles 1981, 15, 213 and references therein.
37. (b). Glover, E. E; Jones, G. J. Chem. Soc. 1958, 3021.
38. 4 (20.0 mg, 0.0173 mmol), and the reaction mixture was stirred at room temperature for 22 h. Next, the solution was concentrated under reduced pressure, and the residue was treated with 3 mL of EtOH (1 and 3) or THF (2). The solid was filtered and washed with ethanol (1 and 3) or EtOAc (2). Purification of the crude product by column chromatography on silica gel (reverse phase) using water as eluent yielded the corresponding biquinolizinium dibromides 1-3.
39. Gaussian 98, Revision A.11; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 2001.