A rapid approach to the synthesis of highly functionalized tetrahydroisoquinolines

Journal of Organic Chemistry

Volumn 74, Issue 4, 2009, Pages 1791-1793

  Thansandote, Praew ^a   Gouliaras, Christina ^a   Turcotte Savard, Marc Olivier ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE; BENZOFURAN DERIVATIVE; CARBON; CHROMENE DERIVATIVE; DIBENZOFURAN; NORBORNENE DERIVATIVE; PALLADIUM; TETRAHYDROBENZOAZEPINE; TETRAHYDROISOQUINOLINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; SYNTHESIS;

AZEPINES; CATALYSIS; KINETICS; PALLADIUM; TETRAHYDROISOQUINOLINES;

EID: 64349087268     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8025725     Document Type: Article

References (40)

1. (a) Saito, E.; Daikuharo, N.; Saito, N. Heterocycles 2007, 74, 411.
2. (b) Ma, M.; Zhao, J.; Wang, S.; Li, S.; Yang, Y.; Shi, J.; Fan, X.; He, L. J. Nat. Prod. 2007, 70, 337.
3. (c) Lane, J. W.; Estevez, A.; Mortada, K.; Callan, O.; Spencer, J. R.; Williams, R. M. Bioorg. Med. Chem. Lett. 2006, 16, 3180.
4. (a) Chafeev, M.; Chowdhury, S.; Fu, J.; Kamboj, R.; Hou, D.; Liu, S. PCT Int. Appl. WO2008046084, 2008.
5. (b) Vohra, R.; Wei, C.-Q.; Gan, Z.; Demnitz, J.; Ahring, P. K. PCT Int. Appl. WO2007115408, 2007.
6. (c) Defert, O.; Leysen, D.; Van Rompaey, P. PCT Int. Appl. WO2008049919, 2008.
7. (d) Chicharro, R.; Alonso, M.; Aran, V. J.; Herradon, B. Tetrahedron Lett. 2008, 49, 2275.
8. (e) Pandey, M. B.; Singh, A. K.; Singh, V. P. Mycobiology 2007, 35, 157.
9. For a recent review, see: Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341.
10. (a) Young, D. D.; Sripada, L.; Deiters, A. J. Comb. Chem. 2007, 9, 735.
11. (b) Alezra, V.; Bonin, M.; Micouin, L.; Husson, H.-P. Tetrahedron Lett. 2001, 42, 2111.
12. (c) Grigg, R.; Inman, M.; Kilner, C.; Köppen, I.; Marchbank, I.; Selby, P.; Sridharan, V. Tetrahedron 2007, 63, 6152.
13. (d) Zhang, Z.; Leitch, D. C.; Lu, M.; Patrick, B. O.; Schafer, L. L. Chem.-Eur. J. 2007, 13, 2012, and references cited therein.
14. Some exceptions: the first two citations in ref 4 and this non-metal example: Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2008, 130, 15720.
15. Flash vacuum pyrolysis with magnesium can form similar products: Aitken, R. A.; Hodgson, P. K. G.; Morrison, J. J.; Oyewale, A. O. J. Chem. Soc., Perkin Trans. 1 2002, 402.
16. (a) Pache, S.; Lautens, M. Org. Lett. 2003, 5, 4827.
17. (b) Jafarpour, F.; Lautens, M. Org. Lett. 2006, 8, 3601.
18. (c) Alberico, D.; Rudolph, A.; Lautens, M. J. Org. Chem. 2007, 72, 775.
19. Microwave irradiation was attempted using the conditions listed in Table 1, entry 1, at 190 °C for 5 min and 170 °C for 10 min, both of which gave messy reactions with unidentifiable products.
20. 2 have been successful catalysts for our palladium-catalyzed, norbornene-mediated domino reactions, and the latter catalyst yielded no product. Only tri-2-furylphosphine and triphenylphosphine have been successful ligands, and the former yielded only traces of product.
21. A major byproduct is the ortho-alkylation/halogen reduction product that presumably forms from palladium oxidatively inserting into the alkyl halide followed by β-hydride elimination. For more on this reaction, see ref 17.
22. Compound 1 was not tried under these conditions.
23. (a) Nordvall, G.; Petersson, C.; Sehgelmeble, F. PCT Int. Appl. WO2007004959, 2007.
24. (b) Hal, I. H.; Wyrick, S. D. Pat. Appl. US85788200, 1987.
25. (c) Kouznetsov, V.; Palma, A.; Salas, S.; Stashenko, E.; Gisela Montenegro, N.; Angel Fontela, G. Heterocycl. Commun. 2000, 6, 519.
26. (d) Briner, K.; Camp, A. M.; Cornell, A.; Mazanetz, M. P.; Rothhaar, R. R.; Victor, F.; Williams, A. C.; Zhang, D. PCT Int. Appl. WO2007028132, 2007.
27. (a) Ramamoorthy, S. P.; Shen, Z.; Harrison, B. L. PCT Int. Appl. WO2006138549, 2006.
28. (b) Montesharei, K.; Lebl, M.; Krahnak, V.; Ni, Y. PCT Int. Appl. WO2001014879, 2001.
29. (c) Schwink, L.; Stengelin, S.; Gossel, M.; Hessler, G.; Haack, T.; Lennig, P. PCT Int. Appl. WO2007093366, 2007.
30. (d) Chen, X.; Chen, X.; Connors, R. V.; Dai, K.; Fu, Y.; Jaen, J. C.; Kim, Y.-J.; Li, L.; Lizarzaburu, M. E.; Mihalic, J. C.; Shuttleworth, S. J. PCT Int. Appl.WO2006020959, 2006.
31. (a) Chouhan, G.; Alper, H. Ore. Lett. 2008, 10, 4987.
32. (b) Zheng, Z.; Alper, H. Ore. Lett. 2008, 10, 4903.
33. Pin, F.; Comesse, S.; Sanselme, M.; Dalch, A. J. Ore. Chem. 2008, 73, 1975.
34. Mechanism based on our own preliminary studies and the work of Catellani and coworkers: (a) Catellani, M.; Fagnola, M. C. Aneew. Chem., Int. Ed. 1994, 33, 2421.
35. (b) Catellani, M.; Frignani, F.; Rangoni, A. Aneew. Chem., Int. Ed. 1997, 36, 119.
36. (c) Faccini, F.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2004, 126, 78.
37. For more information on reductive terminations in Pd-catalyzed, norbornene-mediated domino reactions, see: (a) Mitsudo, K.; Thansandote, P.; Wilhelm, T.; Mariampillai, B.; Lautens, M. Ore. Lett. 2006, 8, 3939.
38. (b) Wilhelm, T.; Lautens, M. Ore. Lett. 2005, 7, 4053.
39. (c) Catellani, M.; Motti, E.; Della Ca', N.; Ferraccioli, R. Eur. J. Ore. Chem. 2007, 4153.
40. (d) Deledda, S.; Motti, E.; Catellani, M. Can. J. Chem. 2005, 83, 741.