Total synthesis of lennoxamine and chilenine via ring-expansion of isoindoloisoquinoline to isoindolobenzazepine

Heterocycles

Volumn 59, Issue 2, 2003, Pages 527-540

  Koseki, Yuji ^a   Katsura, Shinya ^a   Kusano, Shuichi ^a   Sakata, Harumi ^a   Sato, Hiroto ^a   Monzene, Yoshinori ^a   Nagasaka, Tatsuo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BENZAZEPINE DERIVATIVE; BERBERINE DERIVATIVE; CHILENINE; INDOLE ALKALOID; LENNOXAMINE; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHILE; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NONHUMAN; PLANT; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037346083     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-s50     Document Type: Article

References (81)

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13. For the first synthesis of (±)-chilenamine, see: a) C. Schöpf and M. Schweickert, Chem. Ber., 1965, 98, 2566. For other examples, see: b) H. O. Bernhard and V. Snieckus, Tetrahedron Lett., 1971, 4867. c) S. Teitel, W. Klötzer, J. Borgese, and A. Brossi, Can. J. Chem., 1972, 50, 2022. d) S. Yasuda, Y. Sugimoto, C. Mukai, and M. Hanaoka, Heterocycles, 1990, 30, 335.
14. For the first synthesis of (±)-chilenamine, see: a) C. Schöpf and M. Schweickert, Chem. Ber., 1965, 98, 2566. For other examples, see: b) H. O. Bernhard and V. Snieckus, Tetrahedron Lett., 1971, 4867. c) S. Teitel, W. Klötzer, J. Borgese, and A. Brossi, Can. J. Chem., 1972, 50, 2022. d) S. Yasuda, Y. Sugimoto, C. Mukai, and M. Hanaoka, Heterocycles, 1990, 30, 335.
15. For total synthesis of (±)-lennoxamine, see: a) Ref. 3c. b) E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1986, 785. c) C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 1987, 28, 6089. d) C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 1990, 2929. e) Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 1995, 43, 1604. f) G. Rodríguez, M. M. Cid, C. Saá, L. Castedo, and D. Domínguez, J. Org. Chem., 1996, 61, 2780. g) A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 2000, 56, 1491. h) S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 2000, 41, 8007. i) J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3923.
16. For total synthesis of (±)-lennoxamine, see: a) Ref. 3c. b) E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1986, 785. c) C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 1987, 28, 6089. d) C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 1990, 2929. e) Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 1995, 43, 1604. f) G. Rodríguez, M. M. Cid, C. Saá, L. Castedo, and D. Domínguez, J. Org. Chem., 1996, 61, 2780. g) A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 2000, 56, 1491. h) S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 2000, 41, 8007. i) J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3923.
17. For total synthesis of (±)-lennoxamine, see: a) Ref. 3c. b) E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1986, 785. c) C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 1987, 28, 6089. d) C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 1990, 2929. e) Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 1995, 43, 1604. f) G. Rodríguez, M. M. Cid, C. Saá, L. Castedo, and D. Domínguez, J. Org. Chem., 1996, 61, 2780. g) A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 2000, 56, 1491. h) S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 2000, 41, 8007. i) J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3923.
18. For total synthesis of (±)-lennoxamine, see: a) Ref. 3c. b) E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1986, 785. c) C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 1987, 28, 6089. d) C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 1990, 2929. e) Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 1995, 43, 1604. f) G. Rodríguez, M. M. Cid, C. Saá, L. Castedo, and D. Domínguez, J. Org. Chem., 1996, 61, 2780. g) A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 2000, 56, 1491. h) S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 2000, 41, 8007. i) J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3923.
19. For total synthesis of (±)-lennoxamine, see: a) Ref. 3c. b) E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1986, 785. c) C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 1987, 28, 6089. d) C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 1990, 2929. e) Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 1995, 43, 1604. f) G. Rodríguez, M. M. Cid, C. Saá, L. Castedo, and D. Domínguez, J. Org. Chem., 1996, 61, 2780. g) A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 2000, 56, 1491. h) S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 2000, 41, 8007. i) J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3923.
20. For total synthesis of (±)-lennoxamine, see: a) Ref. 3c. b) E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1986, 785. c) C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 1987, 28, 6089. d) C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 1990, 2929. e) Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 1995, 43, 1604. f) G. Rodríguez, M. M. Cid, C. Saá, L. Castedo, and D. Domínguez, J. Org. Chem., 1996, 61, 2780. g) A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 2000, 56, 1491. h) S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 2000, 41, 8007. i) J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3923.
21. For total synthesis of (±)-lennoxamine, see: a) Ref. 3c. b) E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1986, 785. c) C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 1987, 28, 6089. d) C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 1990, 2929. e) Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 1995, 43, 1604. f) G. Rodríguez, M. M. Cid, C. Saá, L. Castedo, and D. Domínguez, J. Org. Chem., 1996, 61, 2780. g) A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 2000, 56, 1491. h) S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 2000, 41, 8007. i) J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3923.
22. For total synthesis of (±)-lennoxamine, see: a) Ref. 3c. b) E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1986, 785. c) C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 1987, 28, 6089. d) C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 1990, 2929. e) Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 1995, 43, 1604. f) G. Rodríguez, M. M. Cid, C. Saá, L. Castedo, and D. Domínguez, J. Org. Chem., 1996, 61, 2780. g) A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 2000, 56, 1491. h) S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 2000, 41, 8007. i) J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3923.
23. For total synthesis of (±)-lennoxamine, see: a) Ref. 3c. b) E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1986, 785. c) C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 1987, 28, 6089. d) C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 1990, 2929. e) Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 1995, 43, 1604. f) G. Rodríguez, M. M. Cid, C. Saá, L. Castedo, and D. Domínguez, J. Org. Chem., 1996, 61, 2780. g) A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 2000, 56, 1491. h) S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 2000, 41, 8007. i) J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3923.
24. For total synthesis of (±)-lennoxamine and (±)-chilenine, see: a) H. Ishibashi, H. Kawanami, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1997, 817. b) Y. Koseki, S. Kusano, H. Sakata, and T. Nagasaka, Tetrahedron Lett., 1999, 40, 2169.
25. For total synthesis of (±)-lennoxamine and (±)-chilenine, see: a) H. Ishibashi, H. Kawanami, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1997, 817. b) Y. Koseki, S. Kusano, H. Sakata, and T. Nagasaka, Tetrahedron Lett., 1999, 40, 2169.
26. For total synthesis of (±)-chilenine, see: a) F. G. Fang and S. J. Danishefsky, Tetrahedron Lett., 1989, 30, 2747. b) H. Ishibashi, H. Kawanami, H. Iriyama, and M. Ikeda, Tetrahedron Lett., 1995, 36, 6733. c) H. Yoda, A. Nakahama, T. Koketsu, and K. Takabe, Tetrahedron Lett., 2002, 43, 4667. Also, see: d) Ref. 2a-c, e-g.
27. For total synthesis of (±)-chilenine, see: a) F. G. Fang and S. J. Danishefsky, Tetrahedron Lett., 1989, 30, 2747. b) H. Ishibashi, H. Kawanami, H. Iriyama, and M. Ikeda, Tetrahedron Lett., 1995, 36, 6733. c) H. Yoda, A. Nakahama, T. Koketsu, and K. Takabe, Tetrahedron Lett., 2002, 43, 4667. Also, see: d) Ref. 2a-c, e-g.
28. For total synthesis of (±)-chilenine, see: a) F. G. Fang and S. J. Danishefsky, Tetrahedron Lett., 1989, 30, 2747. b) H. Ishibashi, H. Kawanami, H. Iriyama, and M. Ikeda, Tetrahedron Lett., 1995, 36, 6733. c) H. Yoda, A. Nakahama, T. Koketsu, and K. Takabe, Tetrahedron Lett., 2002, 43, 4667. Also, see: d) Ref. 2a-c, e-g.
29. For total synthesis of (±)-chilenine, see: a) F. G. Fang and S. J. Danishefsky, Tetrahedron Lett., 1989, 30, 2747. b) H. Ishibashi, H. Kawanami, H. Iriyama, and M. Ikeda, Tetrahedron Lett., 1995, 36, 6733. c) H. Yoda, A. Nakahama, T. Koketsu, and K. Takabe, Tetrahedron Lett., 2002, 43, 4667. Also, see: d) Ref. 2a-c, e-g.
30. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
31. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
32. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
33. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
34. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
35. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
36. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
37. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
38. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
39. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
40. For other synthetic approaches to isoindolobenzazepines, see: a) J. Trojanek, Z. Koblicova, Z. Vesely, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 1975, 40, 681. b) S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 1984, 25, 3485. c) J. Chiefari, W. Janowski, and R. Prager, Tetrahedron Lett., 1986, 27, 6119. d) P. H. Mazzocchi, C. R. King, and H. L. Ammon, Tetrahedron Lett., 1987, 28, 2473. e) S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 1987, 28, 5323. f) M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 1987, 26, 2683. g) J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 1989, 42, 49. h) B. Proksa, D. Uhrin, and A. Vadkerti, Chem. Papers, 1991, 45, 567. i) C. Lamas, C. Saá, L. Castedo, and D. Domínguez, Tetrahedron Lett., 1992, 33, 5653. j) G. Rodríguez, L. Castedo, D. Domínguez, C. Saá, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 877. k) A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 2001, 66, 2414.
41. Part of this work has appeared as a preliminary communication, see: Ref. 5b.
42. The ring-exapansion of pyrroloisoquinoline to pyrrolo[3]benzazepine using this method has been previously reported, see: Y. Koseki, H. Sato, Y. Watanabe, and T. Nagasaka, Org. Lett., 2002, 4, 885.
43. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
44. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
45. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
46. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
47. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
48. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
49. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
50. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
51. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
52. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
53. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
54. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
55. For a review on other ring-expansion of isoquinolines, see: a) T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931. For recent some references not included in the above review, see: b) Ref. 7k. c) M. Kawase, M, Niwa, M. Nozaki, and N. Motohashi, Heterocycles, 1998, 48, 555. d) J. W. Zhang, J. Y. Guo, and X. T. Liang, Chinese Chem. Lett., 1995, 6, 651. e) G. R. Lenz and R. A. Lessor, Org. Synth., 1993, 70, 139. f) M. Kawase, Chem. Commun., 1992, 1076. g) Ref. 7h. h) A. F. Khlebnikov, R. R. Kostikov, and V. S. Shklyaev, Kim. Geterotsikl. Soedin., 1990, 1086 (Chem. Abstr., 1991, 114, 81537c). i) Ref. 4c. j) G. R. Renz, J. Org. Chem., 1988, 53, 5791. k) D. Ben-Ishai, I. Sataty, N. Peled, and R. Goldshare, Tetrahedron, 1987, 43, 439. l) J. R. Pfister, Heterocycles, 1986, 24, 2099. m) H. Bieräugel, H.-P. Soetens, and U. K. Pandit, Heterocycles, 1977, 7, 37
56. a) W. N. Speckamp and M. J. Moolenaar, Tetrahedron, 2000, 56, 3817.
57. b) H. Hiemstra and W. N. Speckamp, "Comprehensive Organic Synthesis", Vol. 2, ed. by B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, p. 1047.
58. a) H. K. Desai and R. N. Usgaonkar, J. Indian Chem. Soc., 1963, 40, 239.
59. And also, see: b) P. Meldrum, Indian Acad. Sci., Sect. A, 1935, 1, 433 and 437.
60. M. Kihara and S. Kobayashi, Chem. Pharm. Bull., 1978, 26, 155.
61. This result has appeared as a preliminary communication, see: Ref. 4e.
62. For recent some examples of the cyclization of o-alkynylbenzamides under basic conditions, see: a) S. F. Vasilevskii and M. S. Shvartsberg, Russian Chem. Bull. 1990, 39, 1901 (Izv. Akad. Nauk SSSR, Ser. Kim., 1990, 39, 2089). b) Ref. 4f. c) M. W. Khan and N. G. Kundu, Synlett, 1997, 1435. d) H. Sashida and A. Kawamukai, Synthesis, 1999, 1145. e) M. M. Cid, D. Domínguez, L. Castedo, and E. M. V.-López, Tetrahedron, 1999, 55, 5599. f) M.-J. Wu, L.-J. Chang, L.-M. Wei, and C.-F. Lin, Tetrahedron, 1999, 55, 13193. g) N. G. Kundu and M. W. Khan, Tetrahedron, 2000, 56, 4777. Cyclization of 3-alkynylpyridine-2-carboxamide derivatives using catalytic amount of bases, see: h) M. Clericuzio, F. Han, F. Pan, Z. Pang, and O. Sterner, Acta Chem. Scand., 1998, 52, 1333.
63. For recent some examples of the cyclization of o-alkynylbenzamides under basic conditions, see: a) S. F. Vasilevskii and M. S. Shvartsberg, Russian Chem. Bull. 1990, 39, 1901 (Izv. Akad. Nauk SSSR, Ser. Kim., 1990, 39, 2089). b) Ref. 4f. c) M. W. Khan and N. G. Kundu, Synlett, 1997, 1435. d) H. Sashida and A. Kawamukai, Synthesis, 1999, 1145. e) M. M. Cid, D. Domínguez, L. Castedo, and E. M. V.-López, Tetrahedron, 1999, 55, 5599. f) M.-J. Wu, L.-J. Chang, L.-M. Wei, and C.-F. Lin, Tetrahedron, 1999, 55, 13193. g) N. G. Kundu and M. W. Khan, Tetrahedron, 2000, 56, 4777. Cyclization of 3-alkynylpyridine-2-carboxamide derivatives using catalytic amount of bases, see: h) M. Clericuzio, F. Han, F. Pan, Z. Pang, and O. Sterner, Acta Chem. Scand., 1998, 52, 1333.
64. For recent some examples of the cyclization of o-alkynylbenzamides under basic conditions, see: a) S. F. Vasilevskii and M. S. Shvartsberg, Russian Chem. Bull. 1990, 39, 1901 (Izv. Akad. Nauk SSSR, Ser. Kim., 1990, 39, 2089). b) Ref. 4f. c) M. W. Khan and N. G. Kundu, Synlett, 1997, 1435. d) H. Sashida and A. Kawamukai, Synthesis, 1999, 1145. e) M. M. Cid, D. Domínguez, L. Castedo, and E. M. V.-López, Tetrahedron, 1999, 55, 5599. f) M.-J. Wu, L.-J. Chang, L.-M. Wei, and C.-F. Lin, Tetrahedron, 1999, 55, 13193. g) N. G. Kundu and M. W. Khan, Tetrahedron, 2000, 56, 4777. Cyclization of 3-alkynylpyridine-2-carboxamide derivatives using catalytic amount of bases, see: h) M. Clericuzio, F. Han, F. Pan, Z. Pang, and O. Sterner, Acta Chem. Scand., 1998, 52, 1333.
65. For recent some examples of the cyclization of o-alkynylbenzamides under basic conditions, see: a) S. F. Vasilevskii and M. S. Shvartsberg, Russian Chem. Bull. 1990, 39, 1901 (Izv. Akad. Nauk SSSR, Ser. Kim., 1990, 39, 2089). b) Ref. 4f. c) M. W. Khan and N. G. Kundu, Synlett, 1997, 1435. d) H. Sashida and A. Kawamukai, Synthesis, 1999, 1145. e) M. M. Cid, D. Domínguez, L. Castedo, and E. M. V.-López, Tetrahedron, 1999, 55, 5599. f) M.-J. Wu, L.-J. Chang, L.-M. Wei, and C.-F. Lin, Tetrahedron, 1999, 55, 13193. g) N. G. Kundu and M. W. Khan, Tetrahedron, 2000, 56, 4777. Cyclization of 3-alkynylpyridine-2-carboxamide derivatives using catalytic amount of bases, see: h) M. Clericuzio, F. Han, F. Pan, Z. Pang, and O. Sterner, Acta Chem. Scand., 1998, 52, 1333.
66. For recent some examples of the cyclization of o-alkynylbenzamides under basic conditions, see: a) S. F. Vasilevskii and M. S. Shvartsberg, Russian Chem. Bull. 1990, 39, 1901 (Izv. Akad. Nauk SSSR, Ser. Kim., 1990, 39, 2089). b) Ref. 4f. c) M. W. Khan and N. G. Kundu, Synlett, 1997, 1435. d) H. Sashida and A. Kawamukai, Synthesis, 1999, 1145. e) M. M. Cid, D. Domínguez, L. Castedo, and E. M. V.-López, Tetrahedron, 1999, 55, 5599. f) M.-J. Wu, L.-J. Chang, L.-M. Wei, and C.-F. Lin, Tetrahedron, 1999, 55, 13193. g) N. G. Kundu and M. W. Khan, Tetrahedron, 2000, 56, 4777. Cyclization of 3-alkynylpyridine-2-carboxamide derivatives using catalytic amount of bases, see: h) M. Clericuzio, F. Han, F. Pan, Z. Pang, and O. Sterner, Acta Chem. Scand., 1998, 52, 1333.
67. For recent some examples of the cyclization of o-alkynylbenzamides under basic conditions, see: a) S. F. Vasilevskii and M. S. Shvartsberg, Russian Chem. Bull. 1990, 39, 1901 (Izv. Akad. Nauk SSSR, Ser. Kim., 1990, 39, 2089). b) Ref. 4f. c) M. W. Khan and N. G. Kundu, Synlett, 1997, 1435. d) H. Sashida and A. Kawamukai, Synthesis, 1999, 1145. e) M. M. Cid, D. Domínguez, L. Castedo, and E. M. V.-López, Tetrahedron, 1999, 55, 5599. f) M.-J. Wu, L.-J. Chang, L.-M. Wei, and C.-F. Lin, Tetrahedron, 1999, 55, 13193. g) N. G. Kundu and M. W. Khan, Tetrahedron, 2000, 56, 4777. Cyclization of 3-alkynylpyridine-2-carboxamide derivatives using catalytic amount of bases, see: h) M. Clericuzio, F. Han, F. Pan, Z. Pang, and O. Sterner, Acta Chem. Scand., 1998, 52, 1333.
68. For recent some examples of the cyclization of o-alkynylbenzamides under basic conditions, see: a) S. F. Vasilevskii and M. S. Shvartsberg, Russian Chem. Bull. 1990, 39, 1901 (Izv. Akad. Nauk SSSR, Ser. Kim., 1990, 39, 2089). b) Ref. 4f. c) M. W. Khan and N. G. Kundu, Synlett, 1997, 1435. d) H. Sashida and A. Kawamukai, Synthesis, 1999, 1145. e) M. M. Cid, D. Domínguez, L. Castedo, and E. M. V.-López, Tetrahedron, 1999, 55, 5599. f) M.-J. Wu, L.-J. Chang, L.-M. Wei, and C.-F. Lin, Tetrahedron, 1999, 55, 13193. g) N. G. Kundu and M. W. Khan, Tetrahedron, 2000, 56, 4777. Cyclization of 3-alkynylpyridine-2-carboxamide derivatives using catalytic amount of bases, see: h) M. Clericuzio, F. Han, F. Pan, Z. Pang, and O. Sterner, Acta Chem. Scand., 1998, 52, 1333.
69. For recent some examples of the cyclization of o-alkynylbenzamides under basic conditions, see: a) S. F. Vasilevskii and M. S. Shvartsberg, Russian Chem. Bull. 1990, 39, 1901 (Izv. Akad. Nauk SSSR, Ser. Kim., 1990, 39, 2089). b) Ref. 4f. c) M. W. Khan and N. G. Kundu, Synlett, 1997, 1435. d) H. Sashida and A. Kawamukai, Synthesis, 1999, 1145. e) M. M. Cid, D. Domínguez, L. Castedo, and E. M. V.-López, Tetrahedron, 1999, 55, 5599. f) M.-J. Wu, L.-J. Chang, L.-M. Wei, and C.-F. Lin, Tetrahedron, 1999, 55, 13193. g) N. G. Kundu and M. W. Khan, Tetrahedron, 2000, 56, 4777. Cyclization of 3-alkynylpyridine-2-carboxamide derivatives using catalytic amount of bases, see: h) M. Clericuzio, F. Han, F. Pan, Z. Pang, and O. Sterner, Acta Chem. Scand., 1998, 52, 1333.
70. 3SnH (0.03 M), the reaction did not occurr and the use of excess n-BuSnH caused hydrostannylation of the exocyclic double bond on dechlorinated product (5).
71. A similar result has been reported by Back et al., see: a) T. G. Back, O. E. Edwards, and G. A. MacAlpine, Tetrahedron Lett., 1977, 2651. Also, see: b) H. O. Bernhard, J. N. Reed, and V. Snieckus, J. Org. Chem., 1977, 42, 1093.
72. A similar result has been reported by Back et al., see: a) T. G. Back, O. E. Edwards, and G. A. MacAlpine, Tetrahedron Lett., 1977, 2651. Also, see: b) H. O. Bernhard, J. N. Reed, and V. Snieckus, J. Org. Chem., 1977, 42, 1093.
73. For recent some examples of the oxidation of enamides by mCPBA or DMD, see: a)W. Adam, D. Reinhardt, H.-U. Reissig, and K. Paulini, Tetrahedron, 1995, 51, 12257. b) L. E. Burgess, E. K. M. Gross, and J. Jurka, Tetrahedron Lett., 1996, 37, 3255. c) T. Luker, H. Hiemstra, and W. N. Speckamp, Tetrahedron Lett., 1996, 37, 8257. d) C. H. Sugisaki, P. J. Carroll, and C. R. D. Carreia, Tetrahedron Lett., 1998, 39, 3413. e) Y. Koseki, S. Kusano, D. Ichi, K. Yoshida, and T. Nagasaka, Tetrahedron, 2000, 56, 8855. f) H. Xiong, R. P. Hsung, L. Shen, and J. M. Hahn, Tetrahedron Lett., 2002, 43, 4449.
74. For recent some examples of the oxidation of enamides by mCPBA or DMD, see: a)W. Adam, D. Reinhardt, H.-U. Reissig, and K. Paulini, Tetrahedron, 1995, 51, 12257. b) L. E. Burgess, E. K. M. Gross, and J. Jurka, Tetrahedron Lett., 1996, 37, 3255. c) T. Luker, H. Hiemstra, and W. N. Speckamp, Tetrahedron Lett., 1996, 37, 8257. d) C. H. Sugisaki, P. J. Carroll, and C. R. D. Carreia, Tetrahedron Lett., 1998, 39, 3413. e) Y. Koseki, S. Kusano, D. Ichi, K. Yoshida, and T. Nagasaka, Tetrahedron, 2000, 56, 8855. f) H. Xiong, R. P. Hsung, L. Shen, and J. M. Hahn, Tetrahedron Lett., 2002, 43, 4449.
75. For recent some examples of the oxidation of enamides by mCPBA or DMD, see: a)W. Adam, D. Reinhardt, H.-U. Reissig, and K. Paulini, Tetrahedron, 1995, 51, 12257. b) L. E. Burgess, E. K. M. Gross, and J. Jurka, Tetrahedron Lett., 1996, 37, 3255. c) T. Luker, H. Hiemstra, and W. N. Speckamp, Tetrahedron Lett., 1996, 37, 8257. d) C. H. Sugisaki, P. J. Carroll, and C. R. D. Carreia, Tetrahedron Lett., 1998, 39, 3413. e) Y. Koseki, S. Kusano, D. Ichi, K. Yoshida, and T. Nagasaka, Tetrahedron, 2000, 56, 8855. f) H. Xiong, R. P. Hsung, L. Shen, and J. M. Hahn, Tetrahedron Lett., 2002, 43, 4449.
76. For recent some examples of the oxidation of enamides by mCPBA or DMD, see: a)W. Adam, D. Reinhardt, H.-U. Reissig, and K. Paulini, Tetrahedron, 1995, 51, 12257. b) L. E. Burgess, E. K. M. Gross, and J. Jurka, Tetrahedron Lett., 1996, 37, 3255. c) T. Luker, H. Hiemstra, and W. N. Speckamp, Tetrahedron Lett., 1996, 37, 8257. d) C. H. Sugisaki, P. J. Carroll, and C. R. D. Carreia, Tetrahedron Lett., 1998, 39, 3413. e) Y. Koseki, S. Kusano, D. Ichi, K. Yoshida, and T. Nagasaka, Tetrahedron, 2000, 56, 8855. f) H. Xiong, R. P. Hsung, L. Shen, and J. M. Hahn, Tetrahedron Lett., 2002, 43, 4449.
77. For recent some examples of the oxidation of enamides by mCPBA or DMD, see: a)W. Adam, D. Reinhardt, H.-U. Reissig, and K. Paulini, Tetrahedron, 1995, 51, 12257. b) L. E. Burgess, E. K. M. Gross, and J. Jurka, Tetrahedron Lett., 1996, 37, 3255. c) T. Luker, H. Hiemstra, and W. N. Speckamp, Tetrahedron Lett., 1996, 37, 8257. d) C. H. Sugisaki, P. J. Carroll, and C. R. D. Carreia, Tetrahedron Lett., 1998, 39, 3413. e) Y. Koseki, S. Kusano, D. Ichi, K. Yoshida, and T. Nagasaka, Tetrahedron, 2000, 56, 8855. f) H. Xiong, R. P. Hsung, L. Shen, and J. M. Hahn, Tetrahedron Lett., 2002, 43, 4449.
78. For recent some examples of the oxidation of enamides by mCPBA or DMD, see: a)W. Adam, D. Reinhardt, H.-U. Reissig, and K. Paulini, Tetrahedron, 1995, 51, 12257. b) L. E. Burgess, E. K. M. Gross, and J. Jurka, Tetrahedron Lett., 1996, 37, 3255. c) T. Luker, H. Hiemstra, and W. N. Speckamp, Tetrahedron Lett., 1996, 37, 8257. d) C. H. Sugisaki, P. J. Carroll, and C. R. D. Carreia, Tetrahedron Lett., 1998, 39, 3413. e) Y. Koseki, S. Kusano, D. Ichi, K. Yoshida, and T. Nagasaka, Tetrahedron, 2000, 56, 8855. f) H. Xiong, R. P. Hsung, L. Shen, and J. M. Hahn, Tetrahedron Lett., 2002, 43, 4449.
79. T. Yamauchi, K. Hattori, K. Nakao, and K. Tamaki, Bull. Chem. Soc. Jpn., 1987, 60, 4015.
80. Hydrogenation of 3a to 1 with 10% Pd-C in AcOEt in 76% yield has been reported, see: Ref. 4h.
81. W. Adam, J. Bialas, and L. Hadjiarapoglou, Chem. Ber., 1991, 124, 2377.