A new methodology for combinatorial synthesis. Preparation of diverse quinoline derivatives using a novel polymer-supported scandium catalyst

Journal of the American Chemical Society

Volumn 118, Issue 37, 1996, Pages 8977-8978

  Kobayashi, Shu ^a   Nagayama, Satoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029813591     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961062l     Document Type: Article

References (49)

1. Borman, S. Chem. Eng. News 1996, Feb 12, 29.
2. For reviews, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Früchtel, J. S.; Jung, G. Angew, Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Lowe, G. Chem. Soc. Rev. 1995, 37, 309. (e) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233. (f) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
3. For reviews, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Früchtel, J. S.; Jung, G. Angew, Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Lowe, G. Chem. Soc. Rev. 1995, 37, 309. (e) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233. (f) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
4. For reviews, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Früchtel, J. S.; Jung, G. Angew, Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Lowe, G. Chem. Soc. Rev. 1995, 37, 309. (e) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233. (f) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
5. For reviews, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Früchtel, J. S.; Jung, G. Angew, Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Lowe, G. Chem. Soc. Rev. 1995, 37, 309. (e) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233. (f) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
6. For reviews, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Früchtel, J. S.; Jung, G. Angew, Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Lowe, G. Chem. Soc. Rev. 1995, 37, 309. (e) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233. (f) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
7. For reviews, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Früchtel, J. S.; Jung, G. Angew, Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Lowe, G. Chem. Soc. Rev. 1995, 37, 309. (e) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233. (f) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
8. We have recently prepared polymer-supported silyl enol ethers and shown the reactions of the enol ethers with imines for the preparation of amino alcohol library. Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809.
9. Quinoline derivatives have been proposed as chemotherapeutic agents with widespread biological activities (malaria, epidemic, cancer, AIDS, etc.) For a review and recent works, see: (a) Ferguson, L. N. Chem. Soc. Rev. 1972, 14, 279. (b) Anzini, M.; Cappelli, A.; Vomero, S.; Giorgi, G.; Langer, T.; Hamon, M.; Merahi, N.; Emerit, B. M.; Cagnotto, A.; Skorupska, M.; Mennini, T.; Pinto, J. C. J. Med. Chem. 1995, 38, 2692. Ghosh, A. K.; Lee, H. Y.; Thompson, W. J.; Culberson, C.; Holloway, M. K.; McKee, S. P.; Munson, P. M.; Duong, T. T.; Smith, A. M.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Huff, J. R.; Anderson, P. S. J. Med. Chem. 1994, 37, 1177. Sarges, R.; Gallagher, A.; Chambers, T. J.; Yeh, L.-A. J. Med. Chem. 1993, 36, 2828. (e) Ife, R. J.; Brown, T. H.; Keeling, D. J.; Leach, C. A.; Meeson, M. L.; Parsons, M. E.; Reavill, D. R.; Theobald, C. J.; Wiggall, K. J. J. Med. Chem. 1992, 35, 3413.
10. Quinoline derivatives have been proposed as chemotherapeutic agents with widespread biological activities (malaria, epidemic, cancer, AIDS, etc.) For a review and recent works, see: (a) Ferguson, L. N. Chem. Soc. Rev. 1972, 14, 279. (b) Anzini, M.; Cappelli, A.; Vomero, S.; Giorgi, G.; Langer, T.; Hamon, M.; Merahi, N.; Emerit, B. M.; Cagnotto, A.; Skorupska, M.; Mennini, T.; Pinto, J. C. J. Med. Chem. 1995, 38, 2692. Ghosh, A. K.; Lee, H. Y.; Thompson, W. J.; Culberson, C.; Holloway, M. K.; McKee, S. P.; Munson, P. M.; Duong, T. T.; Smith, A. M.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Huff, J. R.; Anderson, P. S. J. Med. Chem. 1994, 37, 1177. Sarges, R.; Gallagher, A.; Chambers, T. J.; Yeh, L.-A. J. Med. Chem. 1993, 36, 2828. (e) Ife, R. J.; Brown, T. H.; Keeling, D. J.; Leach, C. A.; Meeson, M. L.; Parsons, M. E.; Reavill, D. R.; Theobald, C. J.; Wiggall, K. J. J. Med. Chem. 1992, 35, 3413.
11. Quinoline derivatives have been proposed as chemotherapeutic agents with widespread biological activities (malaria, epidemic, cancer, AIDS, etc.) For a review and recent works, see: (a) Ferguson, L. N. Chem. Soc. Rev. 1972, 14, 279. (b) Anzini, M.; Cappelli, A.; Vomero, S.; Giorgi, G.; Langer, T.; Hamon, M.; Merahi, N.; Emerit, B. M.; Cagnotto, A.; Skorupska, M.; Mennini, T.; Pinto, J. C. J. Med. Chem. 1995, 38, 2692. Ghosh, A. K.; Lee, H. Y.; Thompson, W. J.; Culberson, C.; Holloway, M. K.; McKee, S. P.; Munson, P. M.; Duong, T. T.; Smith, A. M.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Huff, J. R.; Anderson, P. S. J. Med. Chem. 1994, 37, 1177. Sarges, R.; Gallagher, A.; Chambers, T. J.; Yeh, L.-A. J. Med. Chem. 1993, 36, 2828. (e) Ife, R. J.; Brown, T. H.; Keeling, D. J.; Leach, C. A.; Meeson, M. L.; Parsons, M. E.; Reavill, D. R.; Theobald, C. J.; Wiggall, K. J. J. Med. Chem. 1992, 35, 3413.
12. Quinoline derivatives have been proposed as chemotherapeutic agents with widespread biological activities (malaria, epidemic, cancer, AIDS, etc.) For a review and recent works, see: (a) Ferguson, L. N. Chem. Soc. Rev. 1972, 14, 279. (b) Anzini, M.; Cappelli, A.; Vomero, S.; Giorgi, G.; Langer, T.; Hamon, M.; Merahi, N.; Emerit, B. M.; Cagnotto, A.; Skorupska, M.; Mennini, T.; Pinto, J. C. J. Med. Chem. 1995, 38, 2692. Ghosh, A. K.; Lee, H. Y.; Thompson, W. J.; Culberson, C.; Holloway, M. K.; McKee, S. P.; Munson, P. M.; Duong, T. T.; Smith, A. M.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Huff, J. R.; Anderson, P. S. J. Med. Chem. 1994, 37, 1177. Sarges, R.; Gallagher, A.; Chambers, T. J.; Yeh, L.-A. J. Med. Chem. 1993, 36, 2828. (e) Ife, R. J.; Brown, T. H.; Keeling, D. J.; Leach, C. A.; Meeson, M. L.; Parsons, M. E.; Reavill, D. R.; Theobald, C. J.; Wiggall, K. J. J. Med. Chem. 1992, 35, 3413.
13. Quinoline derivatives have been proposed as chemotherapeutic agents with widespread biological activities (malaria, epidemic, cancer, AIDS, etc.) For a review and recent works, see: (a) Ferguson, L. N. Chem. Soc. Rev. 1972, 14, 279. (b) Anzini, M.; Cappelli, A.; Vomero, S.; Giorgi, G.; Langer, T.; Hamon, M.; Merahi, N.; Emerit, B. M.; Cagnotto, A.; Skorupska, M.; Mennini, T.; Pinto, J. C. J. Med. Chem. 1995, 38, 2692. Ghosh, A. K.; Lee, H. Y.; Thompson, W. J.; Culberson, C.; Holloway, M. K.; McKee, S. P.; Munson, P. M.; Duong, T. T.; Smith, A. M.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Huff, J. R.; Anderson, P. S. J. Med. Chem. 1994, 37, 1177. Sarges, R.; Gallagher, A.; Chambers, T. J.; Yeh, L.-A. J. Med. Chem. 1993, 36, 2828. (e) Ife, R. J.; Brown, T. H.; Keeling, D. J.; Leach, C. A.; Meeson, M. L.; Parsons, M. E.; Reavill, D. R.; Theobald, C. J.; Wiggall, K. J. J. Med. Chem. 1992, 35, 3413.
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18. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
19. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
20. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
21. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
22. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
23. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
24. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
25. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
26. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
27. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
28. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
29. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
30. For quinoline synthesis from N-arylimines, see: (a) Lucchini, V.; Prato. M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (b) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855. Boger, D. L. Tetrahedron 1983, 39, 2869. Kametani, T.; Kasai, H. Stud. Nat. Prod. Chem. 1989, 3, 385. (e) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (f) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (g) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocycl. Chem. 1970, 7, 1353. (h) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (j) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izd. Akad. Nauk SSSR, Ser. Khim. 1963, 2039. (k) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115.
31. For the utility of multiple-component reactions for combinatorial synthesis, see: (a) Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18. 115. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. See also: refs 5b and 5c.
32. For the utility of multiple-component reactions for combinatorial synthesis, see: (a) Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18. 115. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. See also: refs 5b and 5c.
33. For the utility of multiple-component reactions for combinatorial synthesis, see: (a) Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18. 115. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. See also: refs 5b and 5c.
34. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Akelah, A.; Sherrington, D. C. Ibid. 1981, 81, 557. Frechet, J. M. J. Tetrahedron 1981, 37, 663. (Quite recently, we have developed a scandium catalyst immobilized onto Nafion (Nafion-Sc). Unfortunately, this catalyst is not effective for quinoline synthesis, especially in organic solvents. Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256.)
35. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Akelah, A.; Sherrington, D. C. Ibid. 1981, 81, 557. Frechet, J. M. J. Tetrahedron 1981, 37, 663. (Quite recently, we have developed a scandium catalyst immobilized onto Nafion (Nafion-Sc). Unfortunately, this catalyst is not effective for quinoline synthesis, especially in organic solvents. Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256.)
36. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Akelah, A.; Sherrington, D. C. Ibid. 1981, 81, 557. Frechet, J. M. J. Tetrahedron 1981, 37, 663. (Quite recently, we have developed a scandium catalyst immobilized onto Nafion (Nafion-Sc). Unfortunately, this catalyst is not effective for quinoline synthesis, especially in organic solvents. Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256.)
37. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Akelah, A.; Sherrington, D. C. Ibid. 1981, 81, 557. Frechet, J. M. J. Tetrahedron 1981, 37, 663. (Quite recently, we have developed a scandium catalyst immobilized onto Nafion (Nafion-Sc). Unfortunately, this catalyst is not effective for quinoline synthesis, especially in organic solvents. Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256.)
38. Purchased from Aldrich Chemical Co., Inc.
39. (a) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron Lett. 1992, 48, 5691.
40. (b) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1991, 111, 5493.
41. PA-Sc-TAD (3) is fully characterized by elemental analysis. For 3: C, 23.51; H, 3.62; N, 3.33; F, 12.5; S, 6.74; Sc, 2.0. Precise experimental procedures for the preparation of 3 is shown in supporting information.
42. 4 are not necessary.
43. We have found that lanthanide triflates (including scandium inflate) are water-tolerant Lewis acids and efficient catalysts in several synthetic reactions in aqueous media. (a) Kobayashi, S. Synlett 1994, 689. (b) Kobayashi, S. Chem. Lett. 1991, 2187. Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755. Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590. (e) Kobayashi, S.; Ishitani, H. J. Chem. Soc., Chem. Commun. 1995, 1379.
44. We have found that lanthanide triflates (including scandium inflate) are water-tolerant Lewis acids and efficient catalysts in several synthetic reactions in aqueous media. (a) Kobayashi, S. Synlett 1994, 689. (b) Kobayashi, S. Chem. Lett. 1991, 2187. Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755. Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590. (e) Kobayashi, S.; Ishitani, H. J. Chem. Soc., Chem. Commun. 1995, 1379.
45. We have found that lanthanide triflates (including scandium inflate) are water-tolerant Lewis acids and efficient catalysts in several synthetic reactions in aqueous media. (a) Kobayashi, S. Synlett 1994, 689. (b) Kobayashi, S. Chem. Lett. 1991, 2187. Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755. Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590. (e) Kobayashi, S.; Ishitani, H. J. Chem. Soc., Chem. Commun. 1995, 1379.
46. We have found that lanthanide triflates (including scandium inflate) are water-tolerant Lewis acids and efficient catalysts in several synthetic reactions in aqueous media. (a) Kobayashi, S. Synlett 1994, 689. (b) Kobayashi, S. Chem. Lett. 1991, 2187. Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755. Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590. (e) Kobayashi, S.; Ishitani, H. J. Chem. Soc., Chem. Commun. 1995, 1379.
47. We have found that lanthanide triflates (including scandium inflate) are water-tolerant Lewis acids and efficient catalysts in several synthetic reactions in aqueous media. (a) Kobayashi, S. Synlett 1994, 689. (b) Kobayashi, S. Chem. Lett. 1991, 2187. Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755. Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590. (e) Kobayashi, S.; Ishitani, H. J. Chem. Soc., Chem. Commun. 1995, 1379.
48. Electron deficient dienophiles will not work under the conditions, since the present reactions are based on inverse electron-demand aza Diels-Alder reactions.
49. The tetrahydroquinoline derivatives thus obtained are easily oxidized to dihydroquinoline or quinoline derivatives, which could double the size of the library.