Convergent synthesis of 6-substituted phenanthridines via anionic ring closure

Organic Letters

Volumn 4, Issue 2, 2002, Pages 257-259

  Lysén, Morten ^a   Kristensen, Jesper L ^a   Vedsø, Per ^a,b   Begtrup, Mikael ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b NOVO NORDISK A S   (Denmark)

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ARTICLE;

EID: 0009303718     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0170051     Document Type: Article

References (23)

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9. We recently reported a similar approach to the synthesis of substituted pyrazoloquinolines; see: Pawlas, J.; Vedsø, P.; Jakobsen, P.; Huusfeldt, P. O.; Begtrup, M. J. Org. Chem. 2001, 66, 4214-4219.
10. 3 receptor ligands: (b) Cappelli, A.; Anzini, M.; Vomero, S.; Mannuni, L.; Makovec, F.; Doucet, E.; Hamon, M.; Bruni, G.; Romeo, M. R.; Menziani, M. C.; Benedetti, P. G.; Langer, T. J. Med. Chem. 1998, 41, 728-741. Topoisomerase inhibitors: (c) Janin, Y. L.; Croisy, A.; Riou, J.-F.; Bisagni, E. J. Med. Chem. 1993, 36, 3686-3692. (d) Lynch, M. A.; Duval, O.; Sukhanova, A.; Devy, J.; MacKay, S. P.; Waigh, R. D.; Nabiev, I. Bioorg. Med. Chem. Lett. 2001, 11, 2643-2646. Positive ionotropic activity: (e) Heber, D.; Jürgens, J.; Ravens, U.; Schumann, J. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 787-792. Antituberculosis activity: (f) Ishikawa, T. Med. Res. Rev. 2001, 21, 61-72.
11. 3 receptor ligands: (b) Cappelli, A.; Anzini, M.; Vomero, S.; Mannuni, L.; Makovec, F.; Doucet, E.; Hamon, M.; Bruni, G.; Romeo, M. R.; Menziani, M. C.; Benedetti, P. G.; Langer, T. J. Med. Chem. 1998, 41, 728-741. Topoisomerase inhibitors: (c) Janin, Y. L.; Croisy, A.; Riou, J.-F.; Bisagni, E. J. Med. Chem. 1993, 36, 3686-3692. (d) Lynch, M. A.; Duval, O.; Sukhanova, A.; Devy, J.; MacKay, S. P.; Waigh, R. D.; Nabiev, I. Bioorg. Med. Chem. Lett. 2001, 11, 2643-2646. Positive ionotropic activity: (e) Heber, D.; Jürgens, J.; Ravens, U.; Schumann, J. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 787-792. Antituberculosis activity: (f) Ishikawa, T. Med. Res. Rev. 2001, 21, 61-72.
12. 3 receptor ligands: (b) Cappelli, A.; Anzini, M.; Vomero, S.; Mannuni, L.; Makovec, F.; Doucet, E.; Hamon, M.; Bruni, G.; Romeo, M. R.; Menziani, M. C.; Benedetti, P. G.; Langer, T. J. Med. Chem. 1998, 41, 728-741. Topoisomerase inhibitors: (c) Janin, Y. L.; Croisy, A.; Riou, J.-F.; Bisagni, E. J. Med. Chem. 1993, 36, 3686-3692. (d) Lynch, M. A.; Duval, O.; Sukhanova, A.; Devy, J.; MacKay, S. P.; Waigh, R. D.; Nabiev, I. Bioorg. Med. Chem. Lett. 2001, 11, 2643-2646. Positive ionotropic activity: (e) Heber, D.; Jürgens, J.; Ravens, U.; Schumann, J. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 787-792. Antituberculosis activity: (f) Ishikawa, T. Med. Res. Rev. 2001, 21, 61-72.
13. 3 receptor ligands: (b) Cappelli, A.; Anzini, M.; Vomero, S.; Mannuni, L.; Makovec, F.; Doucet, E.; Hamon, M.; Bruni, G.; Romeo, M. R.; Menziani, M. C.; Benedetti, P. G.; Langer, T. J. Med. Chem. 1998, 41, 728-741. Topoisomerase inhibitors: (c) Janin, Y. L.; Croisy, A.; Riou, J.-F.; Bisagni, E. J. Med. Chem. 1993, 36, 3686-3692. (d) Lynch, M. A.; Duval, O.; Sukhanova, A.; Devy, J.; MacKay, S. P.; Waigh, R. D.; Nabiev, I. Bioorg. Med. Chem. Lett. 2001, 11, 2643-2646. Positive ionotropic activity: (e) Heber, D.; Jürgens, J.; Ravens, U.; Schumann, J. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 787-792. Antituberculosis activity: (f) Ishikawa, T. Med. Res. Rev. 2001, 21, 61-72.
14. 3 receptor ligands: (b) Cappelli, A.; Anzini, M.; Vomero, S.; Mannuni, L.; Makovec, F.; Doucet, E.; Hamon, M.; Bruni, G.; Romeo, M. R.; Menziani, M. C.; Benedetti, P. G.; Langer, T. J. Med. Chem. 1998, 41, 728-741. Topoisomerase inhibitors: (c) Janin, Y. L.; Croisy, A.; Riou, J.-F.; Bisagni, E. J. Med. Chem. 1993, 36, 3686-3692. (d) Lynch, M. A.; Duval, O.; Sukhanova, A.; Devy, J.; MacKay, S. P.; Waigh, R. D.; Nabiev, I. Bioorg. Med. Chem. Lett. 2001, 11, 2643-2646. Positive ionotropic activity: (e) Heber, D.; Jürgens, J.; Ravens, U.; Schumann, J. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 787-792. Antituberculosis activity: (f) Ishikawa, T. Med. Res. Rev. 2001, 21, 61-72.
15. 3 receptor ligands: (b) Cappelli, A.; Anzini, M.; Vomero, S.; Mannuni, L.; Makovec, F.; Doucet, E.; Hamon, M.; Bruni, G.; Romeo, M. R.; Menziani, M. C.; Benedetti, P. G.; Langer, T. J. Med. Chem. 1998, 41, 728-741. Topoisomerase inhibitors: (c) Janin, Y. L.; Croisy, A.; Riou, J.-F.; Bisagni, E. J. Med. Chem. 1993, 36, 3686-3692. (d) Lynch, M. A.; Duval, O.; Sukhanova, A.; Devy, J.; MacKay, S. P.; Waigh, R. D.; Nabiev, I. Bioorg. Med. Chem. Lett. 2001, 11, 2643-2646. Positive ionotropic activity: (e) Heber, D.; Jürgens, J.; Ravens, U.; Schumann, J. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 787-792. Antituberculosis activity: (f) Ishikawa, T. Med. Res. Rev. 2001, 21, 61-72.
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18. For a comprehensive list of references see Patra, P. K.; Suresh, J. R.; Ila, H.; Junjappa, H. Tetrahedron 1998, 54, 10167-10178.
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20. Kristensen, J.; Lysén, M.; Vedsø, P.; Begtrup, M. Org. Lett. 2001, 3, 1435-1437.
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22. Attempted addition of lithium diisopropylamide to 1 led to a complex mixture, presumably due to competing ortho-lithiation.
23. 4), and the solvent was evaporated giving the crude product, which was purified by flash chromatography yielding 246 mg (94%) of 3j as colorless crystals, mp 86 °C, reported mp 82-83 °C. Keene, B. R. T.; Turner, G. L. Tetrahedron 1971, 27, 3405-3416.