Intramolecular triple heck reaction. An efficient entry to fused tetracycles with a benzene core

Journal of Organic Chemistry

Volumn 67, Issue 23, 2002, Pages 8280-8283

  Ma, Shengming ^a   Ni, Bukuo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERIFICATION;

ALKYLATION; AMINATION; BENZENE;

SYNTHESIS (CHEMICAL);

1,3,5 TRIBROMO 2,4,6 TRIENYLBENZENE; BENZENE DERIVATIVE; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HECK REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

EID: 0037111699     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0258094     Document Type: Article

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29. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
30. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
31. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
32. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
33. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
34. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
35. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
36. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
37. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
38. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
39. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
40. For isomerization see: (a) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709. (c) Wu, G.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507. For the suppression of isomerization by silver salt additives, see: (d) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130. (e) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. (f) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407. (h) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133. (i) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (j) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121. (k) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015. (l) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. For the suppression of isomerization by thallium salt, see: (m) Carfagna, C.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 261. (n) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687.
41. Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
42. 3, T = 293 (2) K, Z = 2, reflections collected/unique 6797/4840 [R(int) = 0.0363], no observation (I >2.0σ(I)), parameters 403