Microwave-promoted Pd-catalyzed cyanation of aryl triflates: A fast and versatile access to 3-cyano-3-desoxy-10-ketomorphinans

Organic Letters

Volumn 5, Issue 2, 2003, Pages 201-203

  Zhang, Ao ^a   Neumeyer, John L ^a  

^a MCLEAN HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; MORPHINAN DERIVATIVE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID; LIGAND; MESYLIC ACID DERIVATIVE; NITRILE; OPIATE RECEPTOR;

ARTICLE; CATALYSIS; CHEMICAL REACTION; METHODOLOGY; MICROWAVE RADIATION; THERMODYNAMICS; CHEMISTRY; DRUG ANTAGONISM; DRUG POTENTIATION; SYNTHESIS;

CATALYSIS; CYANIDES; LIGANDS; MESYLATES; MICROWAVES; NITRILES; PALLADIUM; RECEPTORS, OPIOID;

EID: 0038341787     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027256p     Document Type: Article

References (41)

1. (a) Chihiro, M.; Nagamoto, H.; Takemura, I.; Kitano, K.; Komatsu, H.; Sekiguchi, K.; Tabusa, F.; Mori, T.; Tominaga, M.; Yabuuchi, Y. J. Med. Chem. 1995, 38, 353-358.
2. (b) Khanna, I. K.; Weier, R. M.; Yu, Y.; Xu, X. D.; Koszyk, F. J.; Collins, P. W.; Koboldt, C. M.; Veenhuizen, A. W.; Perkins, W. E.; Casler, J. J.; Masferrer, J. L.; Zhang, Y. Y.; Gregory, S. A.; Seibert, K.; Isakson, P. C. J. Med. Chem. 1997, 40, 1634-1647.
3. (c) Larock, R. C. Comprehensive Organic Transformations, A Guide to Functional Group Preparations; VCH Publishers: New York, 1989.
4. (d) Diana, G. D.; Cutcliffe, D.; Volkots, D. L.; Mallamo, J. P.; Bailey, T. R.; Vesico, N.; Oglesby, R. C.; Nitz, T. J.; Wetzel, J.; Giranda, V.; Pevear, D. C.; Dutko, F. J. J. Med. Chem. 1993, 36, 3240-3250.
5. (e) Medwid, J. B.; Paul, R.; Baker, J. S.; Brockman, J. A.; Du, M. T.; Hallett, W. A.; Hanifin, J. W.; Hardy, R. A.; Tarrant, M. E.; Torley, L. W.; Wrenn, S. J. Med. Chem. 1990, 33, 1230-1241.
6. (f) Judikins, B. D.; Allen, D. G.: Cook, T. A.; Evans, B.; Sardharwala, T. E. Synth. Commun. 1996, 26, 4351-4367.
7. Neumeyer, J. L.; Bidlack, J. M.; Zong, R. S.; Bakthavachalam, V.; Gao, P.; Cohen, D. J.; Negus, S. S.; Mello, N. K. J. Med. Chem. 2000, 43, 114-122.
8. (a) Andersson, Y.; Långström. B. J. Chem. Soc., Perkin Trans. I 1994, 1395-1400.
9. (b) March, J. Advanced Organic Chemistry; John Wiley & Sons: New York, 1992.
10. (c) Okano, T.; Kiji, J.; Toyooka, Y. Chem. Lett. 1998, 435-426.
11. (d) Patai, S.; Zabicky, J.; Ed.; John Wiley & Sons: New York, 1970.
12. (e) Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synth. Commun. 1994, 24, 887-890.
13. (f) Anderson, B. A.; Bell, E. C.; Ginah, F. O.; Ham, N. K.; Pagh, L. M.; Wepsiec, J. P. J. Org. Chem. 1998, 63, 8224-8228.
14. (g) Corey, E. J.; Hegedus, L. S. J. Am. Chem. Soc. 1969, 91, 1233-1234.
15. (h) Sosnovsky, G.; Krogh, J. A. Synthesis 1978, 703-705.
16. (i) Yamamura, K.; Murahashi, S. Tetrahedron Lett. 1977, 50, 4429-4430.
17. (j) Fizet, C.; Streith, J. Tetrahedron Lett. 1974, 36, 3187-3188.
18. (k) Sekiya, A.; Ishikawa, N. Chem. Lett. 1975, 277-278.
19. (l) Takagi, K.; Okamoto, T.; Sakaibara, Y.; Ohno, A.; Oka, S.; Hayama, N. Bull. Chem. Soc. Jpn. 1975, 48, 3298-3301.
20. (m) Jiang, B.; Kan, Y.; Zhang, A. Tetrahedron 2001, 57 (8), 1581-1584.
21. Ellis, G. P.; Romney-Alexander, T. M. Chem. Rev. 1987, 87, 779-794.
22. (a) Takagi, K.; Sakakibara, Y. Chem. Lett. 1989, 1957.
23. (b) Takagi, K.; Sasaki, K.; Sakakibara, Y. Bull. Chem. Soc. Jpn. 1991, 64, 1118.
24. (c) Kraus, G. A.; Maeda, H. Tetrahedron Lett. 1994, 35, 9189.
25. (d) Nelson, P. H.; Carr, S. F.; Devens, B. H.; Eugui, E. M.; Franco, F.; Gonzalez, C.; Hawley, R. C.; Loughhead, D. G.; Milan, D. J.; Papp, E.; Patterson, J. W.; Rouhafza, S.; Sjogren, E. B.; Smith, D. B.; Stephenson, R. A. ; Talamas, F. X.; Waltos, A.-M.; Weikert, R. J.; Wu, J. C. J. Med. Chem. 1996, 39, 4181.
26. (e) Chambers, M. R. I.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. I 1989, 1365.
27. (f) Almansa, C.; Carceller, E.; Bartoroli, J.; Forn, J. Synth. Commun. 1993, 23, 2965.
28. (g) Uozumi, Y.; Suzuki, N.; Ogiwara, A.; Hayashi, Y. Tetrahedron 1994, 50, 4293.
29. (h) Hedberg, M. H.; Linnanen, T.; Jansen, J. M.; Nordvall, G.; Hjorth, S.; Unelius, L.; Johansson, A. M. J. Med. Chem. 1996, 39, 3503.
30. Selnick, H. G.; Smith, G. R.; Tebben, A. J. Synth. Commun. 1995, 25, 3255.
31. Alterman, M.; Hallberg, A. J. Org. Chem. 2000, 65, 7984-7989.
32. Kubota, H.; Rice, K. C. Tetrahedron Lett. 1998, 39, 2907-2910.
33. (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
34. (b) Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406-16.
35. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105.
36. (d) Coleman, C. M.; MacElroy, J. M. D.; Gallagher, J. F.; O'Shea, D. F. J. Comb. Chem. 2002, 4, 87-93.
37. (e) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717-727.
38. (a) Ritter, K. Synthesis 1993, 735-762.
39. (b) Bengtson, A.; Hallberg, A.; Larhed, M. Org. Lett. 2002, 4, 1231-1233;
40. Wentland, M. P.; Xu, G.; Cioffi, C. L.; Ye, Y.; Duan, W.; Cohen, D. J.; Colasurdo, A. M.; Bidlack, J. M. Bioorg. Med. Chem. Lett. 2000, 10, 183-187.
41. 4 (19 mg, 0.016 mmol), 5 mL of DMF, and a magnetic stir bar. The vessel was sealed with a septum and placed into the microwave cavity. Microwave irradiation was used and the temperature was rapidly increased from room temperature to 200°C. Once 200°C was reached, the reaction mixture was held at this temperature for 15 min and then cooled rapidly to room temperature. The reaction vessel was opened and the contents were poured into a separating funnel. Saturated sodium carbonate and water were added, and the mixture was extracted with ethyl acetate (3 x 50 mL). The extracts were combined, washed with brine, and dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue was subjected to silica gel column chromatography to yield the nitrile compounds.