Novel Phthalimidine Synthesis. Mannich Condensation of o-Phthalaldehyde with Primary Amines using 1,2,3-1H-Benzotriazole and 2-Mercaptoethanol as Dual Synthetic Auxiliaries

Synlett

Volumn 1996, Issue 4, 1996, Pages 353-355

  Takahashi, Ichiro ^a   Kawakami, Teruki ^a   Hirano, Etsushi ^a   Yokota, Hiroshi ^a   Kitajima, Hidehiko ^a  

^a UNIVERSITY OF FUKUI   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000492940     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5438     Document Type: Article

References (58)

1. (a) Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsuchiya, H.; Takahashi, Y.; Matsuma, R. J. Antibiot., 1977, 30, 275;
2. (b) Tamaoki, T.; Nomoto, H.; Takahashi, I.; Kato, Y.; Morimoto, M.; Tomita, F. Biochem. Biophys. Res. Commun., 1986, 135, 397.
3. (c) Funato, N.; Takayanagi, H.; Konda, Y.; Toda, Y.; Harigaya, Y. Tetrahedron Lett., 1994, 35, 1251.
4. (d) Link, J. T.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc., 1995, 117, 552.
5. (a) Nannin, G.; Griraldi, P. N.; Molgora, G.; Biasoli, G.; Spinelli, F.; Logemann, L.; Dradi, E.; Zanni, G.; Buttinoni, A.; Tommasini, R. Arzneim. Forsch., 1973, 23, 1090.
6. (b) Kametani, T.; Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Haga, S.; Shirayama, K. J. Heterocycl. Chem., 1978, 15, 369.
7. (c) Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Haga, S.; Shirayama, K. Japan Kokai Tokkyo Koho, 1978, 149970; Chem. Abstr., 1979, 90, 186785w.
8. (c) Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Haga, S.; Shirayama, K. Japan Kokai Tokkyo Koho, 1978, 149970; Chem. Abstr., 1979, 90, 186785w.
9. (d) Hisamitsu Pharmaceutical Co., Inc. Japan Kokai Tokkyo Koho, 1980, 149257; Chem. Abstr., 1981, 94, 174879z.
10. (d) Hisamitsu Pharmaceutical Co., Inc. Japan Kokai Tokkyo Koho, 1980, 149257; Chem. Abstr., 1981, 94, 174879z.
11. (e) Li, S.; Wang, X.; Guo, H.; Chen, L. Yiyao Gongye, 1985, 16, 543; Chem. Abstr., 1986, 105, 6378n.
12. (e) Li, S.; Wang, X.; Guo, H.; Chen, L. Yiyao Gongye, 1985, 16, 543; Chem. Abstr., 1986, 105, 6378n.
13. (a) Wada, T.; Nakajima, R.; Kurihara, E.; Narumi, S.; Matsuoka, Y.; Goto, G.; Saji, Y.; Fukuda, N. Jpn. J. Pharmacol., 1989, 49, 331.
14. (b) Hussein, Z.; Mulford, D. J.; Bopp, B. A.; Granneman, G. R. Br. J. Clin. Pharmacol., 1993, 36, 351, Chem. Abstr., 1994, 720, 23014t.
15. (b) Hussein, Z.; Mulford, D. J.; Bopp, B. A.; Granneman, G. R. Br. J. Clin. Pharmacol., 1993, 36, 351, Chem. Abstr., 1994, 720, 23014t.
16. (c) Goto, G.; Fukuda, N. Eur. Pat. Appl., 1994, 602814; Chem. Abstr., 1994, 121, 134102k.
17. (c) Goto, G.; Fukuda, N. Eur. Pat. Appl., 1994, 602814; Chem. Abstr., 1994, 121, 134102k.
18. (d) Matoba, H.; Koyama, H.; Kikuta, J. Eur. Pat. Appl., 1994, 610854; Chem. Abstr., 1994, 121, 72998w.
19. (d) Matoba, H.; Koyama, H.; Kikuta, J. Eur. Pat. Appl., 1994, 610854; Chem. Abstr., 1994, 121, 72998w.
20. Examples of the condensation reactions of primary amines with phthalide are as follows. (a) Hessert, J. Ber., 1877, 10, 1445. (b) Rowe, F. M.; Levin, E.; Burns, A. C.; Davies, J. S. H.; Tepper, W. J. Chem. Soc., 1926, 690. (c) Stirling, C. J. M. J. Chem. Soc., 1960, 255. (d) B.A.S.F., Brit. Patent, 1966, 1049007; Chem. Abstr., 1967, 66, 37763q.
21. Examples of the condensation reactions of primary amines with phthalide are as follows. (a) Hessert, J. Der., 1877, 10, 1445. (b) Rowe, F. M.; Levin, E.; Burns, A. C.; Davies, J. S. H.; Tepper, W. J. Chem. Soc., 1926, 690. (c) Stirling, C. J. M. J. Chem. Soc., 1960, 255. (d) B.A.S.F., Brit. Patent, 1966, 1049007; Chem. Abstr., 1967, 66, 37763q.
22. Examples of the condensation reactions of primary amines with phthalide are as follows. (a) Hessert, J. Der., 1877, 10, 1445. (b) Rowe, F. M.; Levin, E.; Burns, A. C.; Davies, J. S. H.; Tepper, W. J. Chem. Soc., 1926, 690. (c) Stirling, C. J. M. J. Chem. Soc., 1960, 255. (d) B.A.S.F., Brit. Patent, 1966, 1049007; Chem. Abstr., 1967, 66, 37763q.
23. Examples of the condensation reactions of primary amines with phthalide are as follows. (a) Hessert, J. Der., 1877, 10, 1445. (b) Rowe, F. M.; Levin, E.; Burns, A. C.; Davies, J. S. H.; Tepper, W. J. Chem. Soc., 1926, 690. (c) Stirling, C. J. M. J. Chem. Soc., 1960, 255. (d) B.A.S.F., Brit. Patent, 1966, 1049007; Chem. Abstr., 1967, 66, 37763q.
24. Examples of the condensation reactions of primary amines with phthalide are as follows. (a) Hessert, J. Der., 1877, 10, 1445. (b) Rowe, F. M.; Levin, E.; Burns, A. C.; Davies, J. S. H.; Tepper, W. J. Chem. Soc., 1926, 690. (c) Stirling, C. J. M. J. Chem. Soc., 1960, 255. (d) B.A.S.F., Brit. Patent, 1966, 1049007; Chem. Abstr., 1967, 66, 37763q.
25. Examples of the Clemmensen type reductions of phthalimides are as follows. (a) Graebe, C.; Pictet, A. Justus Liebigs Ann. Chem., 1888, 247, 302. (b) Gabriel, S. Ber., 1912, 45, 713 (footnote of 724). (c) Sugasawa, S.; Kodama, K. Yakugaku Zasshi, 1943, 63, 96. (d) Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Haga, S.; Shirayama, K. Japan Kokai Tokkyo Koho, 1979, 92954; Chem. Abstr., 1980, 92, P76287u.
26. Examples of the Clemmensen type reductions of phthalimides are as follows. (a) Graebe, C.; Pictet, A. Justus Liebigs Ann. Chem., 1888, 247, 302. (b) Gabriel, S. Ber., 1912, 45, 713 (footnote of 724). (c) Sugasawa, S.; Kodama, K. Yakugaku Zasshi, 1943, 63, 96. (d) Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Haga, S.; Shirayama, K. Japan Kokai Tokkyo Koho, 1979, 92954; Chem. Abstr., 1980, 92, P76287u.
27. Examples of the Clemmensen type reductions of phthalimides are as follows. (a) Graebe, C.; Pictet, A. Justus Liebigs Ann. Chem., 1888, 247, 302. (b) Gabriel, S. Ber., 1912, 45, 713 (footnote of 724). (c) Sugasawa, S.; Kodama, K. Yakugaku Zasshi, 1943, 63, 96. (d) Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Haga, S.; Shirayama, K. Japan Kokai Tokkyo Koho, 1979, 92954; Chem. Abstr., 1980, 92, P76287u.
28. Examples of the Clemmensen type reductions of phthalimides are as follows. (a) Graebe, C.; Pictet, A. Justus Liebigs Ann. Chem., 1888, 247, 302. (b) Gabriel, S. Ber., 1912, 45, 713 (footnote of 724). (c) Sugasawa, S.; Kodama, K. Yakugaku Zasshi, 1943, 63, 96. (d) Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Haga, S.; Shirayama, K. Japan Kokai Tokkyo Koho, 1979, 92954; Chem. Abstr., 1980, 92, P76287u.
29. Examples of the Clemmensen type reductions of phthalimides are as follows. (a) Graebe, C.; Pictet, A. Justus Liebigs Ann. Chem., 1888, 247, 302. (b) Gabriel, S. Ber., 1912, 45, 713 (footnote of 724). (c) Sugasawa, S.; Kodama, K. Yakugaku Zasshi, 1943, 63, 96. (d) Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Haga, S.; Shirayama, K. Japan Kokai Tokkyo Koho, 1979, 92954; Chem. Abstr., 1980, 92, P76287u.
30. Examples of the catalytic insertions of CO to anils are as follows. (a) Murahashi, S. J. Am. Chem. Soc., 1955, 77, 63. (b) Murahashi, S.; Horie, S. Nippon Kagaku Kaishi, 1958, 79, 12. (c) Prichard, W. W. U. S. Patent, 1958, 2841591; Chem. Abstr., 1958, 52, 20197f. (d) Rosenthal, A.; Weir, M. R. S. J. Org. Chem., 1963, 28, 3025.
31. Examples of the catalytic insertions of CO to anils are as follows. (a) Murahashi, S. J. Am. Chem. Soc., 1955, 77, 63. (b) Murahashi, S.; Horie, S. Nippon Kagaku Kaishi, 1958, 79, 12. (c) Prichard, W. W. U. S. Patent, 1958, 2841591; Chem. Abstr., 1958, 52, 20197f. (d) Rosenthal, A.; Weir, M. R. S. J. Org. Chem., 1963, 28, 3025.
32. Examples of the catalytic insertions of CO to anils are as follows. (a) Murahashi, S. J. Am. Chem. Soc., 1955, 77, 63. (b) Murahashi, S.; Horie, S. Nippon Kagaku Kaishi, 1958, 79, 12. (c) Prichard, W. W. U. S. Patent, 1958, 2841591; Chem. Abstr., 1958, 52, 20197f. (d) Rosenthal, A.; Weir, M. R. S. J. Org. Chem., 1963, 28, 3025.
33. Examples of the catalytic insertions of CO to anils are as follows. (a) Murahashi, S. J. Am. Chem. Soc., 1955, 77, 63. (b) Murahashi, S.; Horie, S. Nippon Kagaku Kaishi, 1958, 79, 12. (c) Prichard, W. W. U. S. Patent, 1958, 2841591; Chem. Abstr., 1958, 52, 20197f. (d) Rosenthal, A.; Weir, M. R. S. J. Org. Chem., 1963, 28, 3025.
34. Examples of the catalytic insertions of CO to anils are as follows. (a) Murahashi, S. J. Am. Chem. Soc., 1955, 77, 63. (b) Murahashi, S.; Horie, S. Nippon Kagaku Kaishi, 1958, 79, 12. (c) Prichard, W. W. U. S. Patent, 1958, 2841591; Chem. Abstr., 1958, 52, 20197f. (d) Rosenthal, A.; Weir, M. R. S. J. Org. Chem., 1963, 28, 3025.
35. Examples of the condensation reactions of o-phthalaldehyde with primary amines are as follows. (a) Thiele, J.; Schneider, J. Justus Liebigs Ann. Chem., 1909, 369, 287 (b) Amano, T.; Sakano, T.; Mizukami, S. Yakugaku Zasshi, 1965, 13, 1042. (c) Tsuruta, Y.; Date, Y.; Kohashi, K. J. Chromatogr., 1990, 502, 178. (d) Azumaya, I.; Kagechika, H.; Fujiwara, Y.; Itoh, M.; Yamaguchi, K.; Shudo, K. J. Am. Chem. Soc., 1991, 113, 2833.
36. Examples of the condensation reactions of o-phthalaldehyde with primary amines are as follows. (a) Thiele, J.; Schneider, J. Justus Liebigs Ann. Chem., 1909, 369, 287 (b) Amano, T.; Sakano, T.; Mizukami, S. Yakugaku Zasshi, 1965, 13, 1042. (c) Tsuruta, Y.; Date, Y.; Kohashi, K. J. Chromatogr., 1990, 502, 178. (d) Azumaya, I.; Kagechika, H.; Fujiwara, Y.; Itoh, M.; Yamaguchi, K.; Shudo, K. J. Am. Chem. Soc., 1991, 113, 2833.
37. Examples of the condensation reactions of o-phthalaldehyde with primary amines are as follows. (a) Thiele, J.; Schneider, J. Justus Liebigs Ann. Chem., 1909, 369, 287 (b) Amano, T.; Sakano, T.; Mizukami, S. Yakugaku Zasshi, 1965, 13, 1042. (c) Tsuruta, Y.; Date, Y.; Kohashi, K. J. Chromatogr., 1990, 502, 178. (d) Azumaya, I.; Kagechika, H.; Fujiwara, Y.; Itoh, M.; Yamaguchi, K.; Shudo, K. J. Am. Chem. Soc., 1991, 113, 2833.
38. Examples of the condensation reactions of o-phthalaldehyde with primary amines are as follows. (a) Thiele, J.; Schneider, J. Justus Liebigs Ann. Chem., 1909, 369, 287 (b) Amano, T.; Sakano, T.; Mizukami, S. Yakugaku Zasshi, 1965, 13, 1042. (c) Tsuruta, Y.; Date, Y.; Kohashi, K. J. Chromatogr., 1990, 502, 178. (d) Azumaya, I.; Kagechika, H.; Fujiwara, Y.; Itoh, M.; Yamaguchi, K.; Shudo, K. J. Am. Chem. Soc., 1991, 113, 2833.
39. (a) Katritzky, A. R.; Rachwal, S.; Hitchings, G. J. Tetrahedron, 1991, 47, 2683.
40. (b) Katritzky, A. R.; Takahashi, I.; Fan, W. -Q.; Pernak, J. Synthesis, 1991, 1147.
41. Berge, J. M. U. S. Patent, 1990, 2959374; Chem. Abstr., 1991, 114, 101996g.
42. Berge, J. M. U. S. Patent, 1990, 2959374; Chem. Abstr., 1991, 114, 101996g.
43. Kubota, F. Japan Kokai Tokkyo Koho, 1990, 263824, 263825; Chem. Abstr., 1991, 115, 20292t, 20293u.
44. Kubota, F. Japan Kokai Tokkyo Koho, 1990, 263824, 263825; Chem. Abstr., 1991, 115, 20292t, 20293u.
45. (a) Takahashi, I.; Tsuzuki, M.; Kitajima, H. Chem. Express, 1992, 7, 701.
46. (b) Takahashi, I.; Tsuzuki, M.; Kitajima, H. Chem. Express, 1993, 8, 589.
47. (c) Takahashi, I.; Kitajima, H. Mem. Fac. Eng., Fukui Univ., 1993, 41, 265.
48. (d) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Kitajima, H.; Isa, K. Heterocycles, 1994, 37, 933.
49. (e) Takahashi, I.; Tsuzuki, M.; Keumi, T.; Kitajima, H.; Isa, K.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull., 1994, 42, 947.
50. (f) Isa, K.; Takahashi, I.; Tsuzuki, M.; Yokota, H.; Kitajima, H. Chem. Lett., 1994, 2403.
51. (g) Takahashi, I.; Tsuzuki, M.; Yokota, H.; Monta, T.; Kitajima, H.; Isa, K. Heterocycles, 1996, 43, 11.
52. (a) Simons, Jr., S. S.; Johnson, D. F. J. Am. Chem. Soc., 1976, 98, 7098.
53. (b) Simons, Jr., S. S.; Johnson, D. F. J. Org. Chem., 1978, 43, 2886.
54. (c) Stobaugh, J. F.; Repta, A. J.; Sternson, L. A.; Garren, K. W. Anal. Biochem., 1983, 135, 495.
55. All (new) compounds exhibited satisfactory spectral data and physical constants (including CHN analyses), respectively.
56. (a) Dominh, T.; Johnson, A. L.; Jones, J. E.; Senise, Jr., P. P. J. Org. Chem., 1977, 42, 4217.
57. (b) Nan'ya, S.; Tange, T.; Maekawa, E. J. Heterocycl. Chem., 1985, 22, 449.
58. nPr) was examined by Simons and Johnson (refs 12a-b).