Lewis acid-controlled regioselectivity in reactions of styrenyl systems with benzoquinone monoimides: New regioselective syntheses of substituted 2-aryl-2,3-dihydrobenzofurans, 2-aryl-2,3-dihydroindoles, and 2-arylindoles

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9297-9308

  Engler, Thomas A ^a   Chai, Wenying ^a   LaTessa, Kenneth O ^a,b  

^a UNIVERSITY OF KANSAS   (United States)

^b Stephens College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030477506     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9617068     Document Type: Article

References (37)

1. (a) The Chemistry of Quinonoid Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1988; Vol. II, Parts 1 and 2.
2. (b) Bruce, J. M. In Rodd's Chemistry of Carbon Compounds, 2nd ed.; Coffey, S., Ed.; Elsevier; Amsterdam, 1974; Vol. III (Aromatic Compounds), Part B, Chapter 8.
3. (c) See references cited in Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
4. (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587.
5. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599.
6. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254.
7. (d) Engler, T. A.; Lynch, K. O., Jr.; Reddy, J. P.; Gregory, G. S. Bioorg. Med. Chem. Lett. 1993, 3, 1229-1232.
8. (e) Engler, T. A.; LaTessa, K. O.; Iyengar, R.; Chai, W.; Agrios, K. Bioorg. Med. Chem. 1996, 7, in press.
9. (a) Brown, E. R. In The Chemistry of Quinonoid Compounds; Patai, S.; Rappoport, Z., Eds.; John Wiley and Sons: New York, 1988; Vol. II, Part 2, Chapter 21.
10. (b) Adams, R.; Reifschneider, W. Bull. Chim. Soc. Fr. 1958, 23-65.
11. For preliminary reports, see (a) Engler, T. A.; Lynch, K. O., Jr.; Chai, W.; Meduna, S. P. Tetrahedron Lett. 1995, 36, 2713-2716. (b) Engler, T. A.; Chai, W.; Lynch, K. O., Jr. Tetrahedron Lett. 1995, 36, 7003-7006.
12. For preliminary reports, see (a) Engler, T. A.; Lynch, K. O., Jr.; Chai, W.; Meduna, S. P. Tetrahedron Lett. 1995, 36, 2713-2716. (b) Engler, T. A.; Chai, W.; Lynch, K. O., Jr. Tetrahedron Lett. 1995, 36, 7003-7006.
13. Dihydroquinoline 12 was actually prepared and used as a 2-3:1 mixture of 12 and its 5-methoxy isomer. The minor component did not react in the Lewis acid-promoted reactions with the quinone monoimides and could be recovered cleanly; see references 2e and 4a.
14. 15 and used as is; 1a/f were ∼100% (E), whereas the others were 3.5-15:1 mixtures of (E): (Z)-isomers. The (Z)-isomer did not react competitively with the (E)-isomer; see reference 2a for a discussion of the relative rates of reactions of (E) vs (Z) styrenes with quinones.
15. Regioselective Lewis acid-activation of quinone bisimides has been described in some detail by Boger and others. See reference 3 and (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem Soc. 1988, 110, 4796-4807. (c) Holmes, T. J., Jr.; Lawton, R. G. J. Org. Chem. 1983, 48, 3146-3150. Similarly, regioselective activation of substituted quinones has been reported. (d) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. (e) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (f) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. (g) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For reasons that are not clear, results of some Ti(IV)-promoted quinone Diels-Alder reactions do not always fit this generalization; see, for examples, (h) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. (i) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693. (j) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
16. Regioselective Lewis acid-activation of quinone bisimides has been described in some detail by Boger and others. See reference 3 and (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem Soc. 1988, 110, 4796-4807. (c) Holmes, T. J., Jr.; Lawton, R. G. J. Org. Chem. 1983, 48, 3146-3150. Similarly, regioselective activation of substituted quinones has been reported. (d) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. (e) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (f) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. (g) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For reasons that are not clear, results of some Ti(IV)-promoted quinone Diels-Alder reactions do not always fit this generalization; see, for examples, (h) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. (i) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693. (j) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
17. Regioselective Lewis acid-activation of quinone bisimides has been described in some detail by Boger and others. See reference 3 and (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem Soc. 1988, 110, 4796-4807. (c) Holmes, T. J., Jr.; Lawton, R. G. J. Org. Chem. 1983, 48, 3146-3150. Similarly, regioselective activation of substituted quinones has been reported. (d) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. (e) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (f) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. (g) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For reasons that are not clear, results of some Ti(IV)-promoted quinone Diels-Alder reactions do not always fit this generalization; see, for examples, (h) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. (i) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693. (j) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
18. Regioselective Lewis acid-activation of quinone bisimides has been described in some detail by Boger and others. See reference 3 and (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem Soc. 1988, 110, 4796-4807. (c) Holmes, T. J., Jr.; Lawton, R. G. J. Org. Chem. 1983, 48, 3146-3150. Similarly, regioselective activation of substituted quinones has been reported. (d) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. (e) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (f) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. (g) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For reasons that are not clear, results of some Ti(IV)-promoted quinone Diels-Alder reactions do not always fit this generalization; see, for examples, (h) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. (i) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693. (j) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
19. Regioselective Lewis acid-activation of quinone bisimides has been described in some detail by Boger and others. See reference 3 and (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem Soc. 1988, 110, 4796-4807. (c) Holmes, T. J., Jr.; Lawton, R. G. J. Org. Chem. 1983, 48, 3146-3150. Similarly, regioselective activation of substituted quinones has been reported. (d) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. (e) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (f) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. (g) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For reasons that are not clear, results of some Ti(IV)-promoted quinone Diels-Alder reactions do not always fit this generalization; see, for examples, (h) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. (i) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693. (j) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
20. Regioselective Lewis acid-activation of quinone bisimides has been described in some detail by Boger and others. See reference 3 and (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem Soc. 1988, 110, 4796-4807. (c) Holmes, T. J., Jr.; Lawton, R. G. J. Org. Chem. 1983, 48, 3146-3150. Similarly, regioselective activation of substituted quinones has been reported. (d) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. (e) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (f) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. (g) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For reasons that are not clear, results of some Ti(IV)-promoted quinone Diels-Alder reactions do not always fit this generalization; see, for examples, (h) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. (i) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693. (j) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
21. Regioselective Lewis acid-activation of quinone bisimides has been described in some detail by Boger and others. See reference 3 and (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem Soc. 1988, 110, 4796-4807. (c) Holmes, T. J., Jr.; Lawton, R. G. J. Org. Chem. 1983, 48, 3146-3150. Similarly, regioselective activation of substituted quinones has been reported. (d) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. (e) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (f) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. (g) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For reasons that are not clear, results of some Ti(IV)-promoted quinone Diels-Alder reactions do not always fit this generalization; see, for examples, (h) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. (i) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693. (j) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
22. Regioselective Lewis acid-activation of quinone bisimides has been described in some detail by Boger and others. See reference 3 and (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem Soc. 1988, 110, 4796-4807. (c) Holmes, T. J., Jr.; Lawton, R. G. J. Org. Chem. 1983, 48, 3146-3150. Similarly, regioselective activation of substituted quinones has been reported. (d) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. (e) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (f) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. (g) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For reasons that are not clear, results of some Ti(IV)-promoted quinone Diels-Alder reactions do not always fit this generalization; see, for examples, (h) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. (i) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693. (j) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
23. Regioselective Lewis acid-activation of quinone bisimides has been described in some detail by Boger and others. See reference 3 and (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem Soc. 1988, 110, 4796-4807. (c) Holmes, T. J., Jr.; Lawton, R. G. J. Org. Chem. 1983, 48, 3146-3150. Similarly, regioselective activation of substituted quinones has been reported. (d) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. (e) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (f) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. (g) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For reasons that are not clear, results of some Ti(IV)-promoted quinone Diels-Alder reactions do not always fit this generalization; see, for examples, (h) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. (i) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693. (j) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
24. Regioselective Lewis acid-activation of quinone bisimides has been described in some detail by Boger and others. See reference 3 and (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem Soc. 1988, 110, 4796-4807. (c) Holmes, T. J., Jr.; Lawton, R. G. J. Org. Chem. 1983, 48, 3146-3150. Similarly, regioselective activation of substituted quinones has been reported. (d) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014. (e) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (f) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618. (g) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For reasons that are not clear, results of some Ti(IV)-promoted quinone Diels-Alder reactions do not always fit this generalization; see, for examples, (h) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commum. 1983, 837-838. (i) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New J. Chem. 1990, 14, 689-693. (j) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
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26. 2 complexes as potential intermediates, see reference 2b and references cited therein.
27. 2 complexes as potential intermediates, see reference 2b and references cited therein.
28. 2 complexes as potential intermediates, see reference 2b and references cited therein.
29. 2 complexes as potential intermediates, see reference 2b and references cited therein.
30. 2 complexes as potential intermediates, see reference 2b and references cited therein.
31. The hydrolysis of the bridging N-(phenylsulfonyl)imine, either on workup or silica gel chromatography, is remarkably facile. Even though a basic workup was used, we were unable to find, or detect, a product with this group intact.
32. Eto, M.; Ito, F.; Kitamura, T.; Harano, K. Heterocycles 1996 43, 1159-1163.
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