Platinum(II)-catalyzed intramolecular cyclization of alkynylbenzonitriles: Synthesis of 1-alkoxyisoquinolines and isoquinolones

Tetrahedron Letters

Volumn 51, Issue 49, 2010, Pages 6422-6425

  Li, Jim ^a   Chen, Lijing ^a   Chin, Elbert ^a   Lui, Alfred S ^a   Zecic, Hasim ^a  

^a Roche Palo Alto ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ISOQUINOLINE; PLATINUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 78149282015     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.136     Document Type: Article

References (38)

1. K.W. Bentley The Isoquinoline Alkaloids Vol. 1 1998 Hardwood Academic Amsterdam
2. J.D. Philipson, M.F. Roberts, M.H. Zenk, The Chemistry and Biology of Isoquinoline Alkaloids 1985 Springer New York
3. K.W. Bentley, T. Marrview, and A. Midmar Nat. Prod. Rep. 23 2006 444
4. For recent examples, see: S.-H. Lee, H.T.M. Van, S.H. Yang, K.-T. Lee, Y. Kwon, and W.-J. Cho Bioog. Med. Chem. Lett. 19 2009 2444
5. M.A. Cinelli, B. Cordero, T.S. Dexheimer, Y. Pommier, and M. Cushman Bioorg. Med. Chem. 17 2009 7145
6. H. Gonzalez-Diaz, M. Cruz-Monteagudo, D. Vina, L. Santana, E. Uriarte, and E. De Clercq Bioorg. Med. Chem. Lett. 15 2005 1651
7. P. Oertqvist, S.D. Peterson, E. Aakerblom, T. Gossas, Y.A. Sabnis, R. Fransson, G. Lindeberg, U.H. Danielson, A. Karlen, and A. Sandstroem Bioorg. Med. Chem. 15 2007 1448
8. For recent reviews on synthesis, see: J.A. Joule, and K. Mills Heterocyclic Chemistry 4th ed. 2000 Blackwell Science Ltd Oxford
9. M. Alvarez, and J.A. Joule Isoquinolines D. Black, Science of Synthesis Vol. 15 2005 Thieme Germany 661
10. M. Chrzanowska, and M.D. Rozwadowska Chem. Rev. 104 2004 3341
11. L.E. Fisher, J.M. Muchowski, and R.D. Clark J. Org. Chem. 57 1992 2700
12. R.D. Clark, and A. Jahangir Org. React. 47 1995 1
13. T. Sakamoto, M. Annaka, Y. Kondo, and H. Yamanaka Chem. Pharm. Bull. 34 1986 2754
14. A. Nagarajan, and T.R. Balasubramanian Indian J. Chem., Sect. B: Org. Chem. 28 1989 67
15. V.R. Batchu, D.K. Barange, D. Kumar, B.R. Sreekanth, K. Vyas, E.A. Reddy, and M. Pal Chem. Commun. 19 2007 1966
16. Y.-N. Niu, Z.-Y. Yan, G.-L. Gao, H.-L. Wang, X.-Z. Shu, K.-G. Ji, and Y.-M. Liang J. Org. Chem. 74 2009 2893
17. H. Gao, and J. Zhang Adv. Synth. Catal. 351 2009 85
18. For recent examples, see: I. Nakamura, Y. Sato, and M. Terada J. Am. Chem. Soc. 131 2009 4198
19. X.-Y. Liu, and C.-M. Che Angew. Chem., Int. Ed. 48 2009 2367
20. S. Yang, Z. Li, X. Jian, and C. He Angew. Chem., Int. Ed. 48 2009 3999
21. M. Gruit, D. Michalik, A. Tillack, and M. Beller Angew. Chem., Int. Ed. 48 2009 7212
22. X.-Z. Shu, S.-C. Zhao, K.-G. Ji, Z.-J. Zheng, X.-Y. Liu, and Y.-M. Liang Angew. Chem., Int. Ed. 48 2009 117
23. Z. Guo, M. Cai, J. Jiang, L. Yang, and W. Hu Org. Lett. 12 2010 652
24. For recent examples using Pd, see: S. Roy, S. Roy, B. Neuenswander, D. Hill, and R.C. Larock J. Comb. Chem. 11 2009 1061 and references cited therein
25. For recent examples using Ag, see: S. Su, and J.A. Porco Jr. J. Am. Chem. Soc. 129 2007 7744
26. Y.-S. Yao, and Z.-J. Yao J. Org. Chem. 73 2008 5221
27. For recent examples using Au, see: A. Das, H.-K. Chang, C.-H. Yang, and R.-S. Liu Org. Lett. 10 2008 4061
28. H. Aikawa, S. Tago, K. Umetsu, N. Haginiwa, and N. Asao Tetrahedron 65 2009 1774
29. For recent examples using Cu, see: A.V. Malkov, M.-M. Westwater, A. Gutnov, P. Ramirez-Lopez, F. Friscourt, A. Kadlcikova, J. Hodacova, Z. Rankovic, M. Kotora, and P. Kocovsky Tetrahedron 64 2008 11335
30. M.A. Bennett, and T. Yoshida J. Am. Chem. Soc. 100 1978 1750
31. M.E. Cucciolito, A. de Renzi, G. Roviello, and F. Ruffo Organometallics 27 2008 1351
32. T. Ghaffar, and A.W. Parkins Tetrahedron Lett. 36 1995 8657
33. T. Ghaffar, and A.W. Parkins J. Mol. Catal. A: Chem. 160 2000 249
34. X.-B. Jiang, A.J. Minnaard, B.L. Feringa, and J.G. de Vries J. Org. Chem. 69 2004 2327
35. All ortho-alkynylbenzonitriles were readily prepared via Sonogashira-coupling reaction from commercially available aryl halides and alkynes.
36. A base-prompted cyclization of 2-alkynylbenzonitriles was reported earlier, see: W.-D. Lu, C.-F. Lin, C.-J. Wang, S.-J. Wang, and M.-J. Wu Tetrahedron 58 2002 7315 and references cited therein
37. Representative experimental procedure: A mixture of benzonitrile 1a (100 mg, 0.49 mmol) and hydrido(dimethylphosphinous acid-κP)[hydrogen bis (dimethylphosphinito-κP)]platinum(II) (21 mg, 0.05 mmol) in EtOH (4 mL) was heated to refluxed for 16 h. The reaction was cooled to room temperature and concentrated. The crude product mixture was purified to afford 2-ethoxyisoquinoline 2b (59 mg, 48% yield) as a viscous oil and isoquinolone 3a (16 mg, 15% yield) as a solid upon standing at room temperature.
38. 4) and concentrated to provided analytical pure isoquinolone 3 (64 mg, 97% yield) as a creamy-colored solid.