Aryne intermediates in the synthesis of polynuclear heterocyclic systems (review)

Chemistry of Heterocyclic Compounds

Volumn 48, Issue 4, 2012, Pages 536-547

  Kovalev, I S ^a   Kopchuk, D S ^a,b   Zyryanov, G V ^a,b   Slepukhin, P A ^b   Rusinov, V L ^a,b   Chupakhin, O N ^a,b  

^a URAL FEDERAL UNIVERSITY   (Russian Federation)

^b INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

Author keywords

Aryne intermediates; Cycloaddition; Diels Alder reactions; Dienophiles; Polynuclear heterocyclic systems

Indexed keywords

EID: 85027952676     PISSN: 00093122     EISSN: 15738353     Source Type: Journal    
DOI: 10.1007/s10593-012-1028-9     Document Type: Review

References (57)

1. Y. Kashiwada, A. Aoshima, Y. Ikeshiro, Y.-P. Chen, H. Furukawa, M. Itoigawa, T. Fujioka, K. Mihashi, L. M. Cosentino, S. L. Morris-Natschke, and K.-H. Lee, Bioorg. Med. Chem., 13, 443 (2005).
2. L. L. Bambas (editor), Chemistry of Heterocyclic Compounds: Five-Member Heterocyclic Compounds with Nitrogen and Sulfur or Nitrogen, Sulfur and Oxygen (Except Thiazole), Vol. 4, Published Online 02.01.2008, Print ISBN 9780470375877, Online ISBN 9780470186534. DOI 10.1002/9780470186534.
3. P. Rigo, W. Baratta, K. Siega, G. A. Chelucci, M. Ballico, and S. Magnolia, US Pat. Appl. 20100152448.
4. T. Gunnlaugsson, M. Glynn, G. M. Tocci (nee Hussey), P. E. Kruger, and F. M. Pfeffer, Coord. Chem. Rev., 250, 3094 (2006).
5. M. V. Nandakumar, S. Ghosh, and C. Schneider, Eur. J. Org. Chem., 6393 (2009).
6. A. Tsuboyama, H. Iwawaki, M. Furugori, T. Mukaide, J. Kamatani, S. Igawa, T. Moriyama, S. Miura, T. Takiguchi, S. Okada, M. Hoshino, and K. Ueno, J. Am. Chem. Soc., 125, 12971 (2003).
7. Z. H. Skraup, Monatsh. Chem., 1, 139 (1881).
8. F. Kröhnke, Synthesis, 1 (1976).
9. G. R. Pabst, O. C. Pfüller, and J. Sauer, Tetrahedron, 55, 8045 (1999).
10. A. Rykowski, D. Branowska, and J. Kielak, Tetrahedron Lett., 41, 3657 (2000).
11. V. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, M. M. Ustinova, B. König, and D. N. Kozhevnikov, Tetrahedron, 64, 8963 (2008).
12. Z. Liu, Novel Aryne Chemistry in Organic Synthesis, Iowa State University (2006), 186 p.
13. S. A. Worlikar and R. C. Larock, Curr. Org. Chem., 15, 3214 (2011).
14. H. Pellissier and M. Santelli, Tetrahedron, 59, 701 (2003).
15. H. H. Wenk, M. Winkler, and W. Sander, Angew. Chem., Int. Ed., 42, 502 (2003).
16. K. M. Allan, C. D. Gilmore, and B. M. Stoltz, Angew. Chem., Int. Ed., 50, 4488 (2011).
17. A. E. Goetz, S. M. Bronner, J. D. Cisneros, J. M. Melamed, R. S. Paton, K. N. Houk, and N.K. Garg, Angew. Chem. Int. Ed., 51, 2758 (2012).
18. R. Sanz, Org. Prep. Proced. Int., 40, 219 (2008).
19. R. Webster and M. Lautens, Org. Lett., 11, 4688 (2009).
20. K. Shahlai, S. O. Acquaah, and H. Hart, Org. Synth., 75, 201 (1998).
21. F. M. Raymo, M. F. Parisi, and F. H. Kohnke, Tetrahedron Lett., 34, 5331 (1993).
22. G. Wittig and G. Reichel, Chem. Ber., 96,2851 (1963).
23. M. Lautens, A. Fagnou, and V. Zuni, Org. Lett., 4, 3465 (2002).
24. P. S. Anderson, M. E. Christy, G. F. Lundell, and G. S. Ponticello, Tetrahedron Lett., 16, 2553 (1975).
25. R. D. Giacometti and Y. K. Ramtohul, Synlett, 2010 (2009).
26. T. Thiemann, H. Fujii, D. Ohira, K. Arima, Y. Li, and S. Mataka, New J. Chem., 27, 1377 (2003).
27. P. M. Jackson and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 681 (1990).
28. P. M. Tadross, C. D. Gilmore, P. Bugga, S. C. Virgil, and B. M. Stoltz, Org. Lett., 12, 1224 (2010).
29. C. Gonzalez, E. Guitian, and L. Castedo, Tetrahedron Lett., 37, 405 (1996).
30. A. A. Aly, N. K. Mohamed, A. A. Hassan, and A.-F. E. Mourad, Tetrahedron, 55, 1111 (1999).
31. H. Hussain, E. Kianmehr, and T. Durst, Tetrahedron Lett., 42, 2245 (2001).
32. T. Kitamura, N. Fukatsu, and Y. Fujiwara, J. Org. Chem., 63, 8579 (1998).
33. R. C. Cambie, P. I. Higgs, P. S. Rutledge, and P. D. Woodgate, Aust. J. Chem., 47, 1815 (1994).
34. N. Kakusawa, K. Sakamoto, J. Kurita, and T. Tsuchiya, Heterocycles, 43, 2091 (1996).
35. K. Matsumoto, T. Uchida, K. Aoyama, M. Nishikawa, T. Kuroda, and T. Okamoto, J. Heterocycl. Chem., 25, 1793 (1988).
36. M. G. Reinecke, Tetrahedron, 38, 427 (1982).
37. S. P. Khanapure, B. M. Bhawal, and E. R. Biehl, Heterocycles, 32, 1773 (1991).
38. N. Kakusawa, M. Imamura, J. Kurita, and T. Tsuchiya, Heterocycles, 38, 957 (1994).
39. N. D. Rondan, N. L. Domelsmith, K. N. Houk, A. T. Bowne, and R. H. Levin, Tetrahedron Lett., 35, 3237 (1979).
40. J. M. Caroon and L. E. Fisher, Heterocycles, 32, 459 (1991).
41. S. Tandel, A. Wang, T. C. Holdeman, H. Zhang, and E. R. Biehl, Tetrahedron, 54, 15147 (1998).
42. A. R. Deshmukh and E. R. Biehl, Heterocycles, 34, 99 (1992).
43. A. Wang and E. Biehl, J. Chem. Soc., Perkin Trans. 1, 1461 (1998).
44. A. Wang, H. Zhang, and E. R. Biehl, Heterocycles, 52, 1133 (2000).
45. Z. Liu and R. C. Larock, Org. Lett., 6, 3739 (2004).
46. Z. Liu and R. C. Larock, Tetrahedron, 63, 347 (2007).
47. H. Yoshida, S. Sugiura, and A. Kunai, Org. Lett., 4, 2767 (2002).
48. J. Zhao and R. C. Larock, Org. Lett., 7, 4273 (2005).
49. J. Barluenga, F. J. Fananas, R. Sanz, and Y. Fernandez, Chem.-Eur. J., 8, 2034 (2002).
50. A. M. d'A. Rocha Gonsalves, T. M. V. D. P. Melo, and T. L. Gilchrist, Tetrahedron, 48, 6821 (1992).
51. R. Dhar, W. Huhnermann, T. Kampchen, W. Overheu, and G. Seitz, Chem. Ber., 116, 97 (1983).
52. S. Diring, P. Retailleau, and R. Ziessel, Tetrahedron Lett., 48, 8069 (2007).
53. S. Diring, P. Retailleau, and R. Ziessel, J. Org. Chem., 72, 10181 (2007).
54. M. Girardot, R. Nomak, and J. K. Snyder, J. Org. Chem., 63, 10063 (1998).
55. D. Margetic, Y. Murata, K. Komatsu, and Z. Marinic, Helv. Chim. Acta, 92, 298 (2009).
56. S. C. Benson, J. L. Gross, and J. K. Snyder, J. Org. Chem., 55, 3257 (1990).
57. G. Seitz, R. Hoferichter, and R. Mohr, Angew. Chem., 99, 345 (1987).