A Novel Approach to 2-Arylated Quinolines: Electrocyclization of Alkynyl Imines via Vinylidene Complexes

Organic Letters

Volumn 6, Issue 3, 2004, Pages 353-355

  Sangu, Kenichiro ^a   Fuchibe, Kohei ^a   Akiyama, Takahiko ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; DEUTERIUM; IMINE; QUINOLINE DERIVATIVE; TUNGSTEN DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; ARYLATION; COMPLEX FORMATION; CYCLIZATION;

EID: 1342264153     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036190a     Document Type: Article

References (30)

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7. Recent transition metal-catalyzed synthetic methods: (a) Amii, H.; Kishikawa, Y.; Uneyama, K. Org. Lett. 2001, 3, 1109. (b) Mahanty, J. S.; De, M. ; Das, P.; Kundu, N. G. Tetrahedron 1997, 53, 13397. (c) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (d) Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576 and references therein.
8. Recent transition metal-catalyzed synthetic methods: (a) Amii, H.; Kishikawa, Y.; Uneyama, K. Org. Lett. 2001, 3, 1109. (b) Mahanty, J. S.; De, M. ; Das, P.; Kundu, N. G. Tetrahedron 1997, 53, 13397. (c) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (d) Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576 and references therein.
9. Recent transition metal-catalyzed synthetic methods: (a) Amii, H.; Kishikawa, Y.; Uneyama, K. Org. Lett. 2001, 3, 1109. (b) Mahanty, J. S.; De, M. ; Das, P.; Kundu, N. G. Tetrahedron 1997, 53, 13397. (c) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (d) Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576 and references therein.
10. Recent transition metal-catalyzed synthetic methods: (a) Amii, H.; Kishikawa, Y.; Uneyama, K. Org. Lett. 2001, 3, 1109. (b) Mahanty, J. S.; De, M. ; Das, P.; Kundu, N. G. Tetrahedron 1997, 53, 13397. (c) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (d) Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576 and references therein.
11. Our recent reports on reactions of group 6 metal carbene complexes with imines: (a) Kagoshima, H.; Akiyama, T. J. Am. Chem. Soc. 2000, 122, 11741. (b) Kagoshima, H.; Okamura, T.; Akiyama, T. J. Am. Chem. Soc. 2001, 123, 7182. (c) Sangu, K.; Kagoshima, H.; Fuchibe, K.; Akiyama, T. Org. Lett. 2002, 4, 3967.
12. Our recent reports on reactions of group 6 metal carbene complexes with imines: (a) Kagoshima, H.; Akiyama, T. J. Am. Chem. Soc. 2000, 122, 11741. (b) Kagoshima, H.; Okamura, T.; Akiyama, T. J. Am. Chem. Soc. 2001, 123, 7182. (c) Sangu, K.; Kagoshima, H.; Fuchibe, K.; Akiyama, T. Org. Lett. 2002, 4, 3967.
13. Our recent reports on reactions of group 6 metal carbene complexes with imines: (a) Kagoshima, H.; Akiyama, T. J. Am. Chem. Soc. 2000, 122, 11741. (b) Kagoshima, H.; Okamura, T.; Akiyama, T. J. Am. Chem. Soc. 2001, 123, 7182. (c) Sangu, K.; Kagoshima, H.; Fuchibe, K.; Akiyama, T. Org. Lett. 2002, 4, 3967.
14. 6 in dry THF under Ar for 2 h using a high-pressure mercury lamp (450W).
15. This fact suggests that tungsten was complexed to 2a and was lost during workup or purification.
16. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
17. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
18. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
19. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
20. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
21. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
22. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
23. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
24. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
25. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
26. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
27. For reviews on vinylidene complexes, see: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197. (c) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59. For synthetic use of vinylidene intermediates of group 6 metals, see for examples: (d) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363. (e) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103. (f) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928. (g) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344. (h) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871. (i) Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569. (j) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (k) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518. (l) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 and references therein.
28. Typical Procedure. A slurry of tungsten hexacarbonyl (70 mg, 0.20 mmol) in dry THF (2 mL) was irradiated for 2 h using a high-pressure mercury lamp (450W). To the resulting yellow solution was added 1a (41 mg, 0.20 mmol) in THF (1 mL), and the solution was refluxed for 2 h. After confirmation that alkynyl imine 1a was consumed completely by TLC analysis, the solvent was removed in vacuo and a solution of NMO (70 mg, 0.60 mmol) in dichloromethane was added and stirred at room temperature for 1 h. The reaction mixture was filtered through a small pad of silica gel using ethyl acetate as an eluent. The filtrate was concentrated and purified by preparative TLC (silica gel, 10:1 hexane/ethyl acetate) to afford the quinoline derivative 2a as a yellow solid (28.6 mg, 70%).
29. N-[1-(2-Methylphenyl)prop-2-yn-1-ylidene]aniline (ortho isomer of compound 1j) afforded the corresponding quinoline derivative in 21% yield under the reaction conditions. Steric hindrance of the methyl group might decrease the planarity of the vinylidene intermediate and retard the electrocyclization step.
30. Reactions of alkyl-or alkenyl-substituted alkynyl imines (not aryl alkynyl imines) have not been examined yet due to their difficulties of preparation.