New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization

Heterocycles

Volumn 52, Issue 2, 2000, Pages 761-774

  Kabir, S M Humayun ^a   Miura, Mami ^a   Sasaki, Shigeru ^a   Harada, Genta ^a   Kuwatani, Yoshiyuki ^a   Yoshida, Masato ^a   Iyoda, Masahiko ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METAL; THIOPHENE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0034143308     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-s86     Document Type: Article

References (42)

1. K. Yui, H. Ishida, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 1987, 2339; K. Yui, H. Ishida, Y. Aso, T. Otsubo, F. Ogura, A. Kawamoto, and J. Tanaka, Bull. Chem. Soc. Jpn., 1989, 62, 1547.
2. K. Yui, H. Ishida, Y. Aso, T. Otsubo, and F. Ogura, Chem. Lett., 1987, 2339; K. Yui, H. Ishida, Y. Aso, T. Otsubo, F. Ogura, A. Kawamoto, and J. Tanaka, Bull. Chem. Soc. Jpn., 1989, 62, 1547.
3. J. P. Ferraris and T. L. Lambert, J. Chem. Soc., Chem. Commun., 1991, 1268; H. Brisset, C. Thobie-Gautier, M. Jubault, A. Gorgnes, and J. Roncali, ibid., 1994, 1765; D. A. Torres and J. P. Ferraris, Tetrahedron Lett., 1994, 35, 7589.
4. J. P. Ferraris and T. L. Lambert, J. Chem. Soc., Chem. Commun., 1991, 1268; H. Brisset, C. Thobie-Gautier, M. Jubault, A. Gorgnes, and J. Roncali, ibid., 1994, 1765; D. A. Torres and J. P. Ferraris, Tetrahedron Lett., 1994, 35, 7589.
5. J. P. Ferraris and T. L. Lambert, J. Chem. Soc., Chem. Commun., 1991, 1268; H. Brisset, C. Thobie-Gautier, M. Jubault, A. Gorgnes, and J. Roncali, ibid., 1994, 1765; D. A. Torres and J. P. Ferraris, Tetrahedron Lett., 1994, 35, 7589.
6. Y. Mazaki, N. Hayashi, and K. Kobayashi, J. Chem. Soc., Chem. Commun., 1992, 1381; N. Hayashi, Y. Mazaki, and K. Kobayashi, Tetrahedron Lett., 1994, 35, 5883.
7. Y. Mazaki, N. Hayashi, and K. Kobayashi, J. Chem. Soc., Chem. Commun., 1992, 1381; N. Hayashi, Y. Mazaki, and K. Kobayashi, Tetrahedron Lett., 1994, 35, 5883.
8. K. Takahashi, Pure Appl. Chem., 1993, 127.
9. A. Bolognesi, M. Catellani, S. Destri, R. Zamboni, and C. Taliani, J. Chem. Soc., Chem. Commun., 1988, 247; C. Taliani, G. Ruani, and R. Zanboni, Synth. Met., 1989, 28, C 507; M. Siekierski, J. Przyluski, and J. Plocharski, ibid., 1993, 61, 217; M. Catellani, T. Caronna, and S. V. Meille, J. Chem. Soc., Chem. Commun., 1994, 1911; G. Zotti, A. Berlin, G. Pagani, G. Schiavon, and S. Zecchin, Adv. Mater., 1995, 7, 48.
10. A. Bolognesi, M. Catellani, S. Destri, R. Zamboni, and C. Taliani, J. Chem. Soc., Chem. Commun., 1988, 247; C. Taliani, G. Ruani, and R. Zanboni, Synth. Met., 1989, 28, C 507; M. Siekierski, J. Przyluski, and J. Plocharski, ibid., 1993, 61, 217; M. Catellani, T. Caronna, and S. V. Meille, J. Chem. Soc., Chem. Commun., 1994, 1911; G. Zotti, A. Berlin, G. Pagani, G. Schiavon, and S. Zecchin, Adv. Mater., 1995, 7, 48.
11. A. Bolognesi, M. Catellani, S. Destri, R. Zamboni, and C. Taliani, J. Chem. Soc., Chem. Commun., 1988, 247; C. Taliani, G. Ruani, and R. Zanboni, Synth. Met., 1989, 28, C 507; M. Siekierski, J. Przyluski, and J. Plocharski, ibid., 1993, 61, 217; M. Catellani, T. Caronna, and S. V. Meille, J. Chem. Soc., Chem. Commun., 1994, 1911; G. Zotti, A. Berlin, G. Pagani, G. Schiavon, and S. Zecchin, Adv. Mater., 1995, 7, 48.
12. A. Bolognesi, M. Catellani, S. Destri, R. Zamboni, and C. Taliani, J. Chem. Soc., Chem. Commun., 1988, 247; C. Taliani, G. Ruani, and R. Zanboni, Synth. Met., 1989, 28, C 507; M. Siekierski, J. Przyluski, and J. Plocharski, ibid., 1993, 61, 217; M. Catellani, T. Caronna, and S. V. Meille, J. Chem. Soc., Chem. Commun., 1994, 1911; G. Zotti, A. Berlin, G. Pagani, G. Schiavon, and S. Zecchin, Adv. Mater., 1995, 7, 48.
13. A. Bolognesi, M. Catellani, S. Destri, R. Zamboni, and C. Taliani, J. Chem. Soc., Chem. Commun., 1988, 247; C. Taliani, G. Ruani, and R. Zanboni, Synth. Met., 1989, 28, C 507; M. Siekierski, J. Przyluski, and J. Plocharski, ibid., 1993, 61, 217; M. Catellani, T. Caronna, and S. V. Meille, J. Chem. Soc., Chem. Commun., 1994, 1911; G. Zotti, A. Berlin, G. Pagani, G. Schiavon, and S. Zecchin, Adv. Mater., 1995, 7, 48.
14. F. de Jong and M. J. Janssen, J. Org. Chem., 1971, 36, 1645.
15. A. Kraak, A. K. Wiersema, P. Jordens, and H. Wynberg, Tetrahedron, 1968, 24, 3381.
16. T. Kauffmann, Angew. Chem., 1974, 86, 321; 1979, 91, 1; T. Kauffmann and H. P. Mackowiak, Chem. Ber., 1985, 118, 2343.
17. T. Kauffmann, Angew. Chem., 1974, 86, 321; 1979, 91, 1; T. Kauffmann and H. P. Mackowiak, Chem. Ber., 1985, 118, 2343.
18. T. Kauffmann, Angew. Chem., 1974, 86, 321; 1979, 91, 1; T. Kauffmann and H. P. Mackowiak, Chem. Ber., 1985, 118, 2343.
19. G. H. Posner, 'An Introduction to Synthesis Using Organocopper Reagents,' John Wiley & Sons, New York, p. 113, 1980; R. F. Kovar, M. D. Rausch, and H. Rosenberg, Organometal. Chem. Syn., 1970/1971, 1, 173.
20. G. H. Posner, 'An Introduction to Synthesis Using Organocopper Reagents,' John Wiley & Sons, New York, p. 113, 1980; R. F. Kovar, M. D. Rausch, and H. Rosenberg, Organometal. Chem. Syn., 1970/1971, 1, 173.
21. For the transition metal-catalyzed reactions of organozinc reagents, see: E. Erdik, Tetrahedron, 1992, 48, 9577.
22. Y. Yokoyama, S. Ito, Y. Takahashi, and Y. Murakami, Tetrahedron Lett., 1985, 26, 6457; A. J. Majeed, Ø. Antonsen, T. Benneche, and K. Undheim, Tetrahedron, 1989, 45, 993; M. Mori, N. Kaneta, and M. Shibasaki, J. Org. Chem., 1991, 56, 3486.
23. Y. Yokoyama, S. Ito, Y. Takahashi, and Y. Murakami, Tetrahedron Lett., 1985, 26, 6457; A. J. Majeed, Ø. Antonsen, T. Benneche, and K. Undheim, Tetrahedron, 1989, 45, 993; M. Mori, N. Kaneta, and M. Shibasaki, J. Org. Chem., 1991, 56, 3486.
24. Y. Yokoyama, S. Ito, Y. Takahashi, and Y. Murakami, Tetrahedron Lett., 1985, 26, 6457; A. J. Majeed, Ø. Antonsen, T. Benneche, and K. Undheim, Tetrahedron, 1989, 45, 993; M. Mori, N. Kaneta, and M. Shibasaki, J. Org. Chem., 1991, 56, 3486.
25. M. Iyoda, M. Miura, S. Sasaki, S. M. H. Kabir, Y. Kuwatani, and M. Yoshida, Tetrahedron Lett., 1997, 38, 4581.
26. For the ring cleavage of 3-lithiothiophenes, see: S. Gronowitz and T. Frejd, Acta Chem. Scand., 1973, 27, 2242.
27. A. Rajca, A. Safronov, S. Rajca, C. R. Ross, II, and J. J. Stezowski, J. Am. Chem. Soc., 1996, 118, 7272.
28. For a review, see: G. H. Posner, 'Organic Reactions,' John Wiley & Sons, New York, 1975, Vol. 22, p. 253.
29. P. Jordens, G. Rawson, and H. Wynberg, J. Chem. Soc. C, 1970, 273.
30. J.-P. Gorlier, L. Hamon, J. Levisalles, and J. Wagnon, J. Chem. Soc., Chem. Commun., 1973, 88; B. H. Lipschutz, R. S. Wilhelm, and D. M. Floyd, J. Am. Chem. Soc., 1981, 103, 7672.
31. J.-P. Gorlier, L. Hamon, J. Levisalles, and J. Wagnon, J. Chem. Soc., Chem. Commun., 1973, 88; B. H. Lipschutz, R. S. Wilhelm, and D. M. Floyd, J. Am. Chem. Soc., 1981, 103, 7672.
32. M. Iyoda, S. M. H. Kabir, A. Vorasingha, Y. Kuwatani, and M. Yoshida, Tetrahedron Lett., 1998, 39, 5393.
33. I. Klement, M. Rottluänder, C. E. Tucker, T. N. Majid, and P. Knochel, Tetrahedron, 1996, 52, 7201.
34. J. Tsuji, 'Palladium Reagents and Catalysts: Innovations in Organic Synthesis,' John Wiley & Sons, New York, 1995.
35. T. R. Kelly, Q. Li, and V. Bhushan, Tetrahedron Lett., 1990, 31, 161; R. Grigg, A. Teasdale, and V. Sridharan, ibid., 1991, 32, 3859.
36. T. R. Kelly, Q. Li, and V. Bhushan, Tetrahedron Lett., 1990, 31, 161; R. Grigg, A. Teasdale, and V. Sridharan, ibid., 1991, 32, 3859.
37. S. Gronowitz, Acta Chem. Scand., 1961, 15, 1393.
38. B. Greving, A. Woltermann, and T. Kauffmann, Angew. Chem., 1974, 86, 475; T. Kauffmann, B. Greving, J. König, A. Mitschker, and A. Woltermann, ibid., 1975, 87, 745; T. Kauffmann, B. Greving, R. Kriegesmann, A. Mitschker, and A. Woltermann, Chem. Ber., 1978, 111, 1330.
39. B. Greving, A. Woltermann, and T. Kauffmann, Angew. Chem., 1974, 86, 475; T. Kauffmann, B. Greving, J. König, A. Mitschker, and A. Woltermann, ibid., 1975, 87, 745; T. Kauffmann, B. Greving, R. Kriegesmann, A. Mitschker, and A. Woltermann, Chem. Ber., 1978, 111, 1330.
40. B. Greving, A. Woltermann, and T. Kauffmann, Angew. Chem., 1974, 86, 475; T. Kauffmann, B. Greving, J. König, A. Mitschker, and A. Woltermann, ibid., 1975, 87, 745; T. Kauffmann, B. Greving, R. Kriegesmann, A. Mitschker, and A. Woltermann, Chem. Ber., 1978, 111, 1330.
41. L. J. Pandya and B. D. Tilak, J. Sci. Ind. Res. Sect. B, 1959, 18, 371.
42. M. Gorzynski and D. Rewicki, Liebigs Ann. Chem., 1986, 625.