Chemo- and regioselective assembly of polysubstituted pyridines and isoquinolines from isocyanides, arynes, and terminal alkynes

Journal of Organic Chemistry

Volumn 77, Issue 8, 2012, Pages 3754-3765

  Sha, Feng ^a   Wu, Luling ^a   Huang, Xian ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDER REACTIONS; ALKYNYLS; IMINE ISOMERIZATION; IN-SITU; ISOCYANIDES; ISOQUINOLINES; MULTI-COMPONENT REACTIONS; REACTION SEQUENCES; REGIO-SELECTIVE; SYNTHETIC STRATEGIES; TERMINAL ALKYNE;

CYANIDES; PYRIDINE; REGIOSELECTIVITY;

ACETYLENE;

ALKYNE DERIVATIVE; ARYNE DERIVATIVE; CYANIDE; ISOCYANIDE DERIVATIVE; ISOQUINOLINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL STRUCTURE; DIELS ALDER REACTION;

ALKYNES; CATALYSIS; CYANIDES; CYCLIZATION; ISOQUINOLINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIDINES; STEREOISOMERISM;

EID: 84860186189     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300072x     Document Type: Article

References (59)

1. The Chemistry of Hetrocyclic Compounds; Coppola, G. M., Schuster, H. F., Eds.; Wiley: New York, 1981.
2. Pharmaceutical Chemistry, Drug Synthesis; Roth, H. J., Kleemann, A., Eds.; Prentice Hall Europe: London, 1988; Vol. 1, p 407.
3. Sweetman, B. A.; Müller-Bunz, H.; Guiry, P. J. Tetrahedron Lett. 2005, 46, 4643
4. Michael, J. P. Nat. Prod. Rep. 2005, 22, 627
5. Kletsas, D.; Li, W.; Han, Z.; Papadopoulos, V. Biochem. Pharmacol. 2004, 67, 1927
6. Kozhevnikov, V. N.; Kozhevnikov, D. N.; Nikitina, T. V.; Rusinov, V. L.; Chupakhin, O. L.; Zabel, M.; König, B. J. Org. Chem. 2003, 68, 2882
7. Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752
8. Li, A. H.; Moro, S.; Forsyth, N.; Melman, N.; Ji, X. D.; Jacobsen, K. A. J. Med. Chem. 1999, 42, 706
9. Scriven, E.; Berry, D. Spec. Chem. Mag. 2001, May, 24
10. Milanowski, D. J.; Gustafson, K. R.; Kelley, J. A.; McMahon, J. B. J. Nat. Prod. 2004, 67, 70
11. Morita, H.; Takeya, K.; Itokawa, H. Bioorg. Med. Chem. Lett. 1995, 5, 597
12. Iwasa, K.; Nishiyam, Y.; Ichimaru, M.; Moriyasu, M.; Kim, H. S.; Wataya, Y.; Yamori, T.; Takashi, T.; Lee, D. U. Eur. J. Med. Chem. 1999, 34, 1077
13. Kartsev, V. G. Med. Chem. Res. 2004, 13, 325
14. Muijlwijk-Koezen, J. E.; Timmerman, H.; Link, R.; Goot, H.; IJzerman, A. P. J. Med. Chem. 1998, 41, 3987
15. Coffey, D. S.; Kolis, S. P.; May, S. A. In Progress in Heterocyclic Chemistry; Gribble, G. W.; Gilchrist, T. L., Eds.; Pergamon: Amsterdam, 2002; Vol. 14, Chapter 6.1.
16. Henry, G. D. Tetrahedron 2004, 60, 6043
17. Varela, J. A.; Saá, C. Chem. Rev. 2003, 103, 3787
18. Huang, Q. H.; Larock, R. C. J. Org. Chem. 2003, 68, 980 and references cited therein
19. Ichikawa, J.; Wada, Y.; Miyazaki, H.; Mori, T.; Kuroki, H. Org. Lett. 2003, 5, 1455
20. McCormick, M. M.; Duong, H. A.; Zuo, G.; Louie, J. J. Am. Chem. Soc. 2005, 127, 5030
21. Fletcher, M. D.; Hurst, T. E.; Miles, T. J.; Moody, C. J. Tetrahedron 2006, 62, 5454
22. Evdokimov, N. M.; Magedov, I. V.; Kireev, A. S.; Kornienko, A. Org. Lett. 2006, 8, 899
23. Movassaghi, M.; Hill, M. D. J. Am. Chem. Soc. 2006, 128, 4592
24. Winter, A.; Risch, N. Synthesis 2003, 2667
25. Thomas, A. D.; Asokan, C. V. Tetrahedron Lett. 2002, 43, 2273
26. Tanaka, K.; Mori, H.; Yamamoto, M.; Katsumara, S. J. Org. Chem. 2001, 66, 3099
27. Komatsu, M.; Ohgishi, H.; Takamatsu, S.; Ohshiro, Y.; Agawa, T. Angew. Chem., Int. Ed. 1982, 21, 213
28. Whaley, W. M.; Govindachari, T. R.; Gensler, W. J. In Organic Reactions; Adams, R., Ed.; Wiley: New York, 1951; Vol. 6.
29. Jones, G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 5.
30. Sha, F.; Huang, X. Angew. Chem., Int. Ed. 2009, 48, 3458
31. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211
32. Himeshima, Y.; Kobayashi, H.; Sonoda, T. J. Am. Chem. Soc. 1985, 107, 5286
33. Kessar, S. V. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 483-515.
34. Lui, Z. J.; Larock, R. C. J. Org. Chem. 2007, 72, 223
35. Worlikar, S. A.; Larock, R. C. J. Org. Chem. 2009, 74, 9132
36. Jeganmohan, M.; Bhuvaneswari, S.; Cheng, C.-H. Chem. Asian J. 2010, 5, 153
37. Yoshida, H.; Asatsu, Y.; Mimura, Y.; Ito, Y.; Ohshita, J.; Takaki, K. Angew. Chem., Int. Ed. 2011, 50, 9676
38. Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2004, 45, 8659
39. Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Tetrahedron 2007, 63, 4793
40. Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Angew. Chem., Int. Ed. 2004, 43, 3935
41. Bunnett, J. F.; Pyun, C. J. Org. Chem. 1969, 34, 2035
42. Bunnett, J. F.; Kim, J. K. J. Am. Chem. Soc. 1973, 95, 2254
43. Feng, L.; Kumar, D.; Birney, D. M.; Kerwin, S. M. Org. Lett. 2004, 6, 2059
44. Bernard, V. H.; Howard, A. J. Am. Chem. Soc. 2001, 123, 10214
45. Knorr, R. Chem. Ber 1965, 98, 4038
46. Rigby, J. H.; Laurent, S. J. Org. Chem. 1998, 63, 6742
47. Jeganmohan, M.; Cheng, C. H. Chem. Commun. 2006, 2454
48. Lui, Z. J.; Larock, R. C. J. Org. Chem. 2006, 71, 3198
49. Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Wasserman, H. H., Ed.; Academic Press: New York, 1987; pp 239-299.
50. Boger, D. L. Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon: Oxford, 1991; Vol. 5, pp 473-480.
51. Boger, D. L. Tetrahedron 1983, 39, 2869
52. Behforouz, M.; Ahmadian., M. Tetrahedron 2000, 56, 5259
53. Wojciechowski, K. Eur. J. Org. Chem. 2001, 3587
54. Movassaghi, M.; Hill, M. D. J. Am. Chem. Soc. 2006, 128, 4592
55. Fletcher, M. D.; Hurst, T. E.; Miles, T. J.; Moody, C. J. Tetrahedron 2006, 62, 5454
56. Yoshida, H.; Ikadai, J.; Shudo, M.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2003, 125, 6638
57. Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Synthesis 2002, 1454
58. Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 7280
59. Yoshida, H.; Sugiura, S.; Kunai, A. Org. Lett. 2002, 4, 2767