A streamlined synthesis for 2,7-diformyl-1,8-naphthalenediol

Synlett

Volumn , Issue 4, 2004, Pages 735-737

  Glaser, Thorsten ^a   Liratzis, Ioannis ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Aldehydes; Directed ortho Metalation; Formylation; Lithiation

Indexed keywords

2,6 DIFORMYLPHENOL; 2,7 DIFORMYL 1,8 NAPHTHALENEDIOL; LIGAND; NAPHTHALENE DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIRECTED ORTHO METALATION REACTION; ELECTROCHEMISTRY; MAGNETISM; METHYLATION; PARAMETER; REACTION ANALYSIS; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; X RAY DIFFRACTION;

EID: 1642276849     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817755     Document Type: Article

References (27)

1. (a) Robson, R. Inorg. Nucl. Chem. Lett. 1970, 6, 125.
2. (b) Robson, R. Aust. J. Chem. 1970, 23, 2217.
3. (c) Pilkington, N. H.; Robson, R. Aust. J. Chem. 1970, 23, 2225.
4. See for example: (a) Urbach, F. L. In Metal Ions in Biological Systems, Vol. 12; Sigel, H., Ed.; Marcel Dekker: New York, 1981, 73-115. (b) Spiro, C. L.; Lambert, S. L.; Smith, T. J.; Duesler, E. N.; Gagne, R. R.; Hendrickson, D. N. Inorg. Chem. 1981, 20, 1229. (c) Fenton, D. E.; Okawa, H. Chem. Ber. 1997, 130, 433. (d) Albedyhl, S.; Averbusch-Pouchot, M. T.; Belle, C.; Krebs, B.; Pierre, J. L.; Saint-Aman, E.; Torelli, S. Eur. J. Inorg. Chem. 2001, 1457. (e) Sudbrake, C.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2001, 751. (f) Brooker, S.; Croucher, P. D.; Davidson, T. C.; Dunbar, G. S.; McQuillan, A. J.; Jameson, G. B. Chem. Commun. 1998, 2131. (g) Koval, I. A.; Pursche, D.; Stassen, A. F.; Gamez, P.; Krebs, B.; Reedijk, J. Eur. J. Inorg. Chem. 2003, 1669. (h) Steinfeld, G.; Lozan, V.; Kersting, B. Angew. Chem. Int. Ed. 2003, 42, 2261. (i) Atkins, A. J.; Black, D.; Finn, R. L.; Marin-Becerra, A.; Blake, A. J.; Ruiz-Ramirez, L.; Li, W.-S.; Schröder, M. Dalton Trans. 2003, 1730; and references cited therein.
5. See for example: (a) Urbach, F. L. In Metal Ions in Biological Systems, Vol. 12; Sigel, H., Ed.; Marcel Dekker: New York, 1981, 73-115. (b) Spiro, C. L.; Lambert, S. L.; Smith, T. J.; Duesler, E. N.; Gagne, R. R.; Hendrickson, D. N. Inorg. Chem. 1981, 20, 1229. (c) Fenton, D. E.; Okawa, H. Chem. Ber. 1997, 130, 433. (d) Albedyhl, S.; Averbusch-Pouchot, M. T.; Belle, C.; Krebs, B.; Pierre, J. L.; Saint-Aman, E.; Torelli, S. Eur. J. Inorg. Chem. 2001, 1457. (e) Sudbrake, C.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2001, 751. (f) Brooker, S.; Croucher, P. D.; Davidson, T. C.; Dunbar, G. S.; McQuillan, A. J.; Jameson, G. B. Chem. Commun. 1998, 2131. (g) Koval, I. A.; Pursche, D.; Stassen, A. F.; Gamez, P.; Krebs, B.; Reedijk, J. Eur. J. Inorg. Chem. 2003, 1669. (h) Steinfeld, G.; Lozan, V.; Kersting, B. Angew. Chem. Int. Ed. 2003, 42, 2261. (i) Atkins, A. J.; Black, D.; Finn, R. L.; Marin-Becerra, A.; Blake, A. J.; Ruiz-Ramirez, L.; Li, W.-S.; Schröder, M. Dalton Trans. 2003, 1730; and references cited therein.
6. See for example: (a) Urbach, F. L. In Metal Ions in Biological Systems, Vol. 12; Sigel, H., Ed.; Marcel Dekker: New York, 1981, 73-115. (b) Spiro, C. L.; Lambert, S. L.; Smith, T. J.; Duesler, E. N.; Gagne, R. R.; Hendrickson, D. N. Inorg. Chem. 1981, 20, 1229. (c) Fenton, D. E.; Okawa, H. Chem. Ber. 1997, 130, 433. (d) Albedyhl, S.; Averbusch-Pouchot, M. T.; Belle, C.; Krebs, B.; Pierre, J. L.; Saint-Aman, E.; Torelli, S. Eur. J. Inorg. Chem. 2001, 1457. (e) Sudbrake, C.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2001, 751. (f) Brooker, S.; Croucher, P. D.; Davidson, T. C.; Dunbar, G. S.; McQuillan, A. J.; Jameson, G. B. Chem. Commun. 1998, 2131. (g) Koval, I. A.; Pursche, D.; Stassen, A. F.; Gamez, P.; Krebs, B.; Reedijk, J. Eur. J. Inorg. Chem. 2003, 1669. (h) Steinfeld, G.; Lozan, V.; Kersting, B. Angew. Chem. Int. Ed. 2003, 42, 2261. (i) Atkins, A. J.; Black, D.; Finn, R. L.; Marin-Becerra, A.; Blake, A. J.; Ruiz-Ramirez, L.; Li, W.-S.; Schröder, M. Dalton Trans. 2003, 1730; and references cited therein.
7. See for example: (a) Urbach, F. L. In Metal Ions in Biological Systems, Vol. 12; Sigel, H., Ed.; Marcel Dekker: New York, 1981, 73-115. (b) Spiro, C. L.; Lambert, S. L.; Smith, T. J.; Duesler, E. N.; Gagne, R. R.; Hendrickson, D. N. Inorg. Chem. 1981, 20, 1229. (c) Fenton, D. E.; Okawa, H. Chem. Ber. 1997, 130, 433. (d) Albedyhl, S.; Averbusch-Pouchot, M. T.; Belle, C.; Krebs, B.; Pierre, J. L.; Saint-Aman, E.; Torelli, S. Eur. J. Inorg. Chem. 2001, 1457. (e) Sudbrake, C.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2001, 751. (f) Brooker, S.; Croucher, P. D.; Davidson, T. C.; Dunbar, G. S.; McQuillan, A. J.; Jameson, G. B. Chem. Commun. 1998, 2131. (g) Koval, I. A.; Pursche, D.; Stassen, A. F.; Gamez, P.; Krebs, B.; Reedijk, J. Eur. J. Inorg. Chem. 2003, 1669. (h) Steinfeld, G.; Lozan, V.; Kersting, B. Angew. Chem. Int. Ed. 2003, 42, 2261. (i) Atkins, A. J.; Black, D.; Finn, R. L.; Marin-Becerra, A.; Blake, A. J.; Ruiz-Ramirez, L.; Li, W.-S.; Schröder, M. Dalton Trans. 2003, 1730; and references cited therein.
8. See for example: (a) Urbach, F. L. In Metal Ions in Biological Systems, Vol. 12; Sigel, H., Ed.; Marcel Dekker: New York, 1981, 73-115. (b) Spiro, C. L.; Lambert, S. L.; Smith, T. J.; Duesler, E. N.; Gagne, R. R.; Hendrickson, D. N. Inorg. Chem. 1981, 20, 1229. (c) Fenton, D. E.; Okawa, H. Chem. Ber. 1997, 130, 433. (d) Albedyhl, S.; Averbusch-Pouchot, M. T.; Belle, C.; Krebs, B.; Pierre, J. L.; Saint-Aman, E.; Torelli, S. Eur. J. Inorg. Chem. 2001, 1457. (e) Sudbrake, C.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2001, 751. (f) Brooker, S.; Croucher, P. D.; Davidson, T. C.; Dunbar, G. S.; McQuillan, A. J.; Jameson, G. B. Chem. Commun. 1998, 2131. (g) Koval, I. A.; Pursche, D.; Stassen, A. F.; Gamez, P.; Krebs, B.; Reedijk, J. Eur. J. Inorg. Chem. 2003, 1669. (h) Steinfeld, G.; Lozan, V.; Kersting, B. Angew. Chem. Int. Ed. 2003, 42, 2261. (i) Atkins, A. J.; Black, D.; Finn, R. L.; Marin-Becerra, A.; Blake, A. J.; Ruiz-Ramirez, L.; Li, W.-S.; Schröder, M. Dalton Trans. 2003, 1730; and references cited therein.
9. See for example: (a) Urbach, F. L. In Metal Ions in Biological Systems, Vol. 12; Sigel, H., Ed.; Marcel Dekker: New York, 1981, 73-115. (b) Spiro, C. L.; Lambert, S. L.; Smith, T. J.; Duesler, E. N.; Gagne, R. R.; Hendrickson, D. N. Inorg. Chem. 1981, 20, 1229. (c) Fenton, D. E.; Okawa, H. Chem. Ber. 1997, 130, 433. (d) Albedyhl, S.; Averbusch-Pouchot, M. T.; Belle, C.; Krebs, B.; Pierre, J. L.; Saint-Aman, E.; Torelli, S. Eur. J. Inorg. Chem. 2001, 1457. (e) Sudbrake, C.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2001, 751. (f) Brooker, S.; Croucher, P. D.; Davidson, T. C.; Dunbar, G. S.; McQuillan, A. J.; Jameson, G. B. Chem. Commun. 1998, 2131. (g) Koval, I. A.; Pursche, D.; Stassen, A. F.; Gamez, P.; Krebs, B.; Reedijk, J. Eur. J. Inorg. Chem. 2003, 1669. (h) Steinfeld, G.; Lozan, V.; Kersting, B. Angew. Chem. Int. Ed. 2003, 42, 2261. (i) Atkins, A. J.; Black, D.; Finn, R. L.; Marin-Becerra, A.; Blake, A. J.; Ruiz-Ramirez, L.; Li, W.-S.; Schröder, M. Dalton Trans. 2003, 1730; and references cited therein.
10. See for example: (a) Urbach, F. L. In Metal Ions in Biological Systems, Vol. 12; Sigel, H., Ed.; Marcel Dekker: New York, 1981, 73-115. (b) Spiro, C. L.; Lambert, S. L.; Smith, T. J.; Duesler, E. N.; Gagne, R. R.; Hendrickson, D. N. Inorg. Chem. 1981, 20, 1229. (c) Fenton, D. E.; Okawa, H. Chem. Ber. 1997, 130, 433. (d) Albedyhl, S.; Averbusch-Pouchot, M. T.; Belle, C.; Krebs, B.; Pierre, J. L.; Saint-Aman, E.; Torelli, S. Eur. J. Inorg. Chem. 2001, 1457. (e) Sudbrake, C.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2001, 751. (f) Brooker, S.; Croucher, P. D.; Davidson, T. C.; Dunbar, G. S.; McQuillan, A. J.; Jameson, G. B. Chem. Commun. 1998, 2131. (g) Koval, I. A.; Pursche, D.; Stassen, A. F.; Gamez, P.; Krebs, B.; Reedijk, J. Eur. J. Inorg. Chem. 2003, 1669. (h) Steinfeld, G.; Lozan, V.; Kersting, B. Angew. Chem. Int. Ed. 2003, 42, 2261. (i) Atkins, A. J.; Black, D.; Finn, R. L.; Marin-Becerra, A.; Blake, A. J.; Ruiz-Ramirez, L.; Li, W.-S.; Schröder, M. Dalton Trans. 2003, 1730; and references cited therein.
11. See for example: (a) Urbach, F. L. In Metal Ions in Biological Systems, Vol. 12; Sigel, H., Ed.; Marcel Dekker: New York, 1981, 73-115. (b) Spiro, C. L.; Lambert, S. L.; Smith, T. J.; Duesler, E. N.; Gagne, R. R.; Hendrickson, D. N. Inorg. Chem. 1981, 20, 1229. (c) Fenton, D. E.; Okawa, H. Chem. Ber. 1997, 130, 433. (d) Albedyhl, S.; Averbusch-Pouchot, M. T.; Belle, C.; Krebs, B.; Pierre, J. L.; Saint-Aman, E.; Torelli, S. Eur. J. Inorg. Chem. 2001, 1457. (e) Sudbrake, C.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2001, 751. (f) Brooker, S.; Croucher, P. D.; Davidson, T. C.; Dunbar, G. S.; McQuillan, A. J.; Jameson, G. B. Chem. Commun. 1998, 2131. (g) Koval, I. A.; Pursche, D.; Stassen, A. F.; Gamez, P.; Krebs, B.; Reedijk, J. Eur. J. Inorg. Chem. 2003, 1669. (h) Steinfeld, G.; Lozan, V.; Kersting, B. Angew. Chem. Int. Ed. 2003, 42, 2261. (i) Atkins, A. J.; Black, D.; Finn, R. L.; Marin-Becerra, A.; Blake, A. J.; Ruiz-Ramirez, L.; Li, W.-S.; Schröder, M. Dalton Trans. 2003, 1730; and references cited therein.
12. See for example: (a) Urbach, F. L. In Metal Ions in Biological Systems, Vol. 12; Sigel, H., Ed.; Marcel Dekker: New York, 1981, 73-115. (b) Spiro, C. L.; Lambert, S. L.; Smith, T. J.; Duesler, E. N.; Gagne, R. R.; Hendrickson, D. N. Inorg. Chem. 1981, 20, 1229. (c) Fenton, D. E.; Okawa, H. Chem. Ber. 1997, 130, 433. (d) Albedyhl, S.; Averbusch-Pouchot, M. T.; Belle, C.; Krebs, B.; Pierre, J. L.; Saint-Aman, E.; Torelli, S. Eur. J. Inorg. Chem. 2001, 1457. (e) Sudbrake, C.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2001, 751. (f) Brooker, S.; Croucher, P. D.; Davidson, T. C.; Dunbar, G. S.; McQuillan, A. J.; Jameson, G. B. Chem. Commun. 1998, 2131. (g) Koval, I. A.; Pursche, D.; Stassen, A. F.; Gamez, P.; Krebs, B.; Reedijk, J. Eur. J. Inorg. Chem. 2003, 1669. (h) Steinfeld, G.; Lozan, V.; Kersting, B. Angew. Chem. Int. Ed. 2003, 42, 2261. (i) Atkins, A. J.; Black, D.; Finn, R. L.; Marin-Becerra, A.; Blake, A. J.; Ruiz-Ramirez, L.; Li, W.-S.; Schröder, M. Dalton Trans. 2003, 1730; and references cited therein.
13. See for example: Glaser, T.; Lügger, T. Inorg. Chim. Acta 2002, 337, 103; and references cited therein.
14. (a) Crisp, G. T.; Turner, P. D. Tetrahedron 2000, 56, 407.
15. ( b) Albrecht, M. Synthesis 1996, 230.
16. Shorthill, B. J.; Granucci, R. G.; Powell, D. R.; Glass, T. E. J. Org. Chem. 2002, 67, 904.
17. (a) Duff, J. C.; Bills, E. J. J. Chem. Soc. 1934, 1305.
18. (b) Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939.
19. Nagata, W.; Okada, K.; Aoki, T. Synthesis 1979, 365.
20. Casiraghi, G.; Casnati, G.; Puglia, G.; Sartori, G.; Terenghi, G. J. Chem. Soc., Perkin Trans. 1 1980, 1862.
21. (a) Gschwend, H. W.; Rodriguez, H. R. Org. React. 1979, 26, 1.
22. (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
23. Winkle, M. R.; Ronald, R. C. J. Org. Chem. 1982, 47, 2101.
24. Poirier, M.; Simard, M.; Wuest, J. D. Organometallics 1996, 15, 1296.
25. CCDC 220283 (2) and CCDC 220284 (3) contain the supplementary crystallographic data of these structures. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the CCDC, 12 Union Road, Cambridge CB 2 1EZ, UK; fax:+44(1223)336033; e-mail:deposit@ccdc.cam.ac. uk].
26. 2O (10 mL) at O°.C. After stirring the reaction mixture for 5 h at r.t., DMF (3.76 mL, 24.17 mmol) was added at O°C and the resulting mixture stirred for another 4 h at r.t. After addition of water (40 mL) and stirring for 1 h at r.t., the pH of the reaction solution was raised to 7-8 by addition of dilute HCl. Standard workup and column chromatography gave 1.62 g (66%) of 3 as a brownish yellow solid.
27. Hoskins, B. F.; McKenzie, C. J.; Robson, R. J. Chem. Soc., Dalton Trans. 1992, 3083.