Efficient Synthesis of 1-Amino-2-naphthalenecarboxylic Acid Derivatives via a Sequential Michael Addition/Enolate-Nitrile Coupling Route and Its Application to Facile Preparation of 9-Amino Analogues of Arylnaphthofuranone Lignans

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 664-668

  Kobayashi, Kazuhiro ^a   Uneda, Tomokazu ^a   Takada, Keiichiro ^a   Tanaka, Hiroto ^a   Kitamura, Tomohide ^a   Morikawa, Osamu ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; LIGNAN DERIVATIVE; NAPHTHO[2,3 C]FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0031027535     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961744r     Document Type: Article

References (38)

1. For a review, see: Gilcgrist, T. L. In The Chemistry of Triple-Bonded Functional Groups; Patai, S., Rappoport, Z., Eds.; J. Wiley & Sons: New York, 1983; p 383.
2. For a review on early work, see: Taylor, E. C.; McKillop, A. The Chemistry of Cyclic Enaminonitriles and o-Aminonitriles; Inter-science: New York, 1970; p 79. For recent reports, see Groundwater, P. W.; Solomons, K. R. H. J. Chem. Soc., Perkin Trans. 1 1994, 173. Besson, T.; Emayan, K.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1995, 1419 and references therein.
3. For a review on early work, see: Taylor, E. C.; McKillop, A. The Chemistry of Cyclic Enaminonitriles and o-Aminonitriles; Inter-science: New York, 1970; p 79. For recent reports, see Groundwater, P. W.; Solomons, K. R. H. J. Chem. Soc., Perkin Trans. 1 1994, 173. Besson, T.; Emayan, K.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1995, 1419 and references therein.
4. For a review on early work, see: Taylor, E. C.; McKillop, A. The Chemistry of Cyclic Enaminonitriles and o-Aminonitriles; Inter-science: New York, 1970; p 79. For recent reports, see Groundwater, P. W.; Solomons, K. R. H. J. Chem. Soc., Perkin Trans. 1 1994, 173. Besson, T.; Emayan, K.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1995, 1419 and references therein.
5. Petridou-Fischer, J.; Papadopoulos, E. P. J. Heterocycl. Chem. 1984, 21, 1333. Reddy, M. S.; Rathan, C. V. Bull. Chem. Soc. Jpn. 1985, 58, 2449. Zhang,W.; Koehler, K. F.; Harris, B.; Skolnik, P.; Cook, J. M. J. Med. Chem. 1994, 37, 745 and references therein. See also: Saupe, T.; Kast, J.; Misslitz, U.; Hagen, H.; Nilz, G.; Pfister, J. Eur. Pat. Appl. EP 456,090; Chem. Abstr. 1992, 116, 193941c.
6. Petridou-Fischer, J.; Papadopoulos, E. P. J. Heterocycl. Chem. 1984, 21, 1333. Reddy, M. S.; Rathan, C. V. Bull. Chem. Soc. Jpn. 1985, 58, 2449. Zhang,W.; Koehler, K. F.; Harris, B.; Skolnik, P.; Cook, J. M. J. Med. Chem. 1994, 37, 745 and references therein. See also: Saupe, T.; Kast, J.; Misslitz, U.; Hagen, H.; Nilz, G.; Pfister, J. Eur. Pat. Appl. EP 456,090; Chem. Abstr. 1992, 116, 193941c.
7. Petridou-Fischer, J.; Papadopoulos, E. P. J. Heterocycl. Chem. 1984, 21, 1333. Reddy, M. S.; Rathan, C. V. Bull. Chem. Soc. Jpn. 1985, 58, 2449. Zhang,W.; Koehler, K. F.; Harris, B.; Skolnik, P.; Cook, J. M. J. Med. Chem. 1994, 37, 745 and references therein. See also: Saupe, T.; Kast, J.; Misslitz, U.; Hagen, H.; Nilz, G.; Pfister, J. Eur. Pat. Appl. EP 456,090; Chem. Abstr. 1992, 116, 193941c.
8. Petridou-Fischer, J.; Papadopoulos, E. P. J. Heterocycl. Chem. 1984, 21, 1333. Reddy, M. S.; Rathan, C. V. Bull. Chem. Soc. Jpn. 1985, 58, 2449. Zhang,W.; Koehler, K. F.; Harris, B.; Skolnik, P.; Cook, J. M. J. Med. Chem. 1994, 37, 745 and references therein. See also: Saupe, T.; Kast, J.; Misslitz, U.; Hagen, H.; Nilz, G.; Pfister, J. Eur. Pat. Appl. EP 456,090; Chem. Abstr. 1992, 116, 193941c.
9. For earlier reports on methods to prepare 1-amino-2-naphtha-lenecarboxylic acid derivatives, see: (a) Campaigne, E.; Maulding, D. R.; Roelofs, W. L. J. Org. Chem. 1964, 29, 1543. (b) Wildeman, J.; Borgen, P. C.; Pluim, H.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron Lett. 1978, 2213. (c) Tomioka, Y.; Ohkubo, K.; Yamazaki, M. Chem. Pharm. Bull. 1985, 33, 1360. (d) Zhang, W.; Liu, R.; Cook, J. M. Heterocycles 1993, 36, 2229. (e) Wilamowski, J.; Osman, D.; Machaj, A.; Kawalek, B.; Sepiol, J. J. J. Prakt. Chem. / Chem. Ztg. 1995, 337, 234. These methods often suffer from a lack of generality and/or simplicity of the operation. For previous syntheses of 2-amino-3-naphthalenecarboxylic acid derivatives, see references cited in ref 5.
10. For earlier reports on methods to prepare 1-amino-2-naphtha-lenecarboxylic acid derivatives, see: (a) Campaigne, E.; Maulding, D. R.; Roelofs, W. L. J. Org. Chem. 1964, 29, 1543. (b) Wildeman, J.; Borgen, P. C.; Pluim, H.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron Lett. 1978, 2213. (c) Tomioka, Y.; Ohkubo, K.; Yamazaki, M. Chem. Pharm. Bull. 1985, 33, 1360. (d) Zhang, W.; Liu, R.; Cook, J. M. Heterocycles 1993, 36, 2229. (e) Wilamowski, J.; Osman, D.; Machaj, A.; Kawalek, B.; Sepiol, J. J. J. Prakt. Chem. / Chem. Ztg. 1995, 337, 234. These methods often suffer from a lack of generality and/or simplicity of the operation. For previous syntheses of 2-amino-3-naphthalenecarboxylic acid derivatives, see references cited in ref 5.
11. For earlier reports on methods to prepare 1-amino-2-naphtha-lenecarboxylic acid derivatives, see: (a) Campaigne, E.; Maulding, D. R.; Roelofs, W. L. J. Org. Chem. 1964, 29, 1543. (b) Wildeman, J.; Borgen, P. C.; Pluim, H.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron Lett. 1978, 2213. (c) Tomioka, Y.; Ohkubo, K.; Yamazaki, M. Chem. Pharm. Bull. 1985, 33, 1360. (d) Zhang, W.; Liu, R.; Cook, J. M. Heterocycles 1993, 36, 2229. (e) Wilamowski, J.; Osman, D.; Machaj, A.; Kawalek, B.; Sepiol, J. J. J. Prakt. Chem. / Chem. Ztg. 1995, 337, 234. These methods often suffer from a lack of generality and/or simplicity of the operation. For previous syntheses of 2-amino-3-naphthalenecarboxylic acid derivatives, see references cited in ref 5.
12. For earlier reports on methods to prepare 1-amino-2-naphtha-lenecarboxylic acid derivatives, see: (a) Campaigne, E.; Maulding, D. R.; Roelofs, W. L. J. Org. Chem. 1964, 29, 1543. (b) Wildeman, J.; Borgen, P. C.; Pluim, H.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron Lett. 1978, 2213. (c) Tomioka, Y.; Ohkubo, K.; Yamazaki, M. Chem. Pharm. Bull. 1985, 33, 1360. (d) Zhang, W.; Liu, R.; Cook, J. M. Heterocycles 1993, 36, 2229. (e) Wilamowski, J.; Osman, D.; Machaj, A.; Kawalek, B.; Sepiol, J. J. J. Prakt. Chem. / Chem. Ztg. 1995, 337, 234. These methods often suffer from a lack of generality and/or simplicity of the operation. For previous syntheses of 2-amino-3-naphthalenecarboxylic acid derivatives, see references cited in ref 5.
13. For earlier reports on methods to prepare 1-amino-2-naphtha-lenecarboxylic acid derivatives, see: (a) Campaigne, E.; Maulding, D. R.; Roelofs, W. L. J. Org. Chem. 1964, 29, 1543. (b) Wildeman, J.; Borgen, P. C.; Pluim, H.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron Lett. 1978, 2213. (c) Tomioka, Y.; Ohkubo, K.; Yamazaki, M. Chem. Pharm. Bull. 1985, 33, 1360. (d) Zhang, W.; Liu, R.; Cook, J. M. Heterocycles 1993, 36, 2229. (e) Wilamowski, J.; Osman, D.; Machaj, A.; Kawalek, B.; Sepiol, J. J. J. Prakt. Chem. / Chem. Ztg. 1995, 337, 234. These methods often suffer from a lack of generality and/or simplicity of the operation. For previous syntheses of 2-amino-3-naphthalenecarboxylic acid derivatives, see references cited in ref 5.
14. Kobayashi, K.; Kanno, Y.; Seko, S.; Suginome, H. J. Chem. Soc., Chem. Commun. 1992, 780. J. Chem. Soc., Perkin Trans. 1 1992, 3111.
15. Kobayashi, K.; Kanno, Y.; Seko, S.; Suginome, H. J. Chem. Soc., Chem. Commun. 1992, 780. J. Chem. Soc., Perkin Trans. 1 1992, 3111.
16. 2 and its application to the synthesis of heterocycles, see: Boyce, W. T.; Levine, R. J. Org. Chem. 1966, 31, 3807. Bradsher, C. K.; Wallis, T. G. J. Org. Chem. 1978, 43, 3817.
17. 2 and its application to the synthesis of heterocycles, see: Boyce, W. T.; Levine, R. J. Org. Chem. 1966, 31, 3807. Bradsher, C. K.; Wallis, T. G. J. Org. Chem. 1978, 43, 3817.
18. 2 and its application to the synthesis of heterocycles, see: Boyce, W. T.; Levine, R. J. Org. Chem. 1966, 31, 3807. Bradsher, C. K.; Wallis, T. G. J. Org. Chem. 1978, 43, 3817.
19. Part of this paper has been reported as a preliminary communication: Kobayashi, K.; Takada, K.; Tanaka, H.; Uneda, T.; Kitamura,T.; Morikawa, O.; Konishi, H. Chem. Lett. 1996, 25.
20. (a) Dirstine, P. H.; Bergstorm, F. W. J. Org. Chem. 1946, 11, 55.
21. (b) Ebert, G. W.; Rieke, R. D. J. Org. Chem. 1988, 53, 4482.
22. Snyder; H. R.; Poos, G. I. J. Am. Chem. Soc. 1949, 71, 1057.
23. Pridgen, L. N.; Snyder, L.; Prol, J., Jr. J. Org. Chem. 1989, 54, 1523.
24. (a) Aquila, H. Justus Liebigs Ann. Chem. 1969, 721, 220.
25. (b) Ishii, H.; Ishikawa, T.; Wada, H.; Miyazaki, H.; Harayama, T. Chem. Pharm. Bull. 1992, 40, 2614.
26. Mukaiyama, T. Org. React. 1982, 28, 203.
27. Kagan, H. B.; Suen, Y.-H. Bull. Soc. Chim. Fr. 1966, 1819. Hiyama, T.; Kobayashi, K. Tetrahedron Lett. 1982, 23, 1597. Hannick, S. M.; Kishi, Y. J. Org. Chem. 1983, 48, 3833.
28. Kagan, H. B.; Suen, Y.-H. Bull. Soc. Chim. Fr. 1966, 1819. Hiyama, T.; Kobayashi, K. Tetrahedron Lett. 1982, 23, 1597. Hannick, S. M.; Kishi, Y. J. Org. Chem. 1983, 48, 3833.
29. Kagan, H. B.; Suen, Y.-H. Bull. Soc. Chim. Fr. 1966, 1819. Hiyama, T.; Kobayashi, K. Tetrahedron Lett. 1982, 23, 1597. Hannick, S. M.; Kishi, Y. J. Org. Chem. 1983, 48, 3833.
30. (a) Kobayashi, K.; Tokimatsu, J.; Maeda, K.; Morikawa, O.; Konishi, H. J. Chem. Soc., Perkin Trans. 1 1995, 3013.
31. (b) Hattori, T.; Tanaka, H.; Okaishi, Y.; Miyano, S. J. Chem. Soc., Perkin Trans. 1 1995, 235.
32. (c) Cochran, J. E.; Padwa. A. J. Org. Chem. 1995, 60, 3938.
33. (d) Ogiku, T.; Yoshida, S.; Ohmizu, H.; Iwasaki, T. J. Org. Chem. 1995, 60, 4585.
34. (e) Tanabe, Y.; Seko, S.; Nishii, Y.; Yoshida, T.; Utsumi, N.; Suzukamo, G. J. Chem. Soc., Perkin Trans. 1 1996, 2157.
35. (f) Ward, R. S. Synthesis 1992, 719.
36. (g) Ayres, C. D.; Loike, J. D. Lignans; Cambridge Univ. Press: Cambridge, 1990.
37. (h) Ward, R. S. Nat. Prod. Rep. 1993, 10, 1.
38. (j) Ward, R. S. Nat. Prod. Rep. 1995, 12, 183 and references cited therein.