A new route to papaverine analogs via photocyclization of substituted N-acyl-α-dehydrophenylalaninamides

Heterocycles

Volumn 60, Issue 8, 2003, Pages 1779-1786

  Hoshina, Hideki ^a   Maekawa, Kei ^a   Taie, Keisuke ^a   Igarashi, Tetsutaro ^a   Sakurai, Tadamitsu ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DEHYDRO AMINO ACID; 3,4 DIMETHOXYBENZALDEHYDE; AZETIDINE DERIVATIVE; BENZALDEHYDE DERIVATIVE; HETEROCYCLIC COMPOUND; METHANOL; N PHENYLACETYL ALPHA DEHYDRO(3,4 DIMETHOXYPHENYL)ALANINAMIDE; PAPAVERINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; IRRADIATION; ISOMER; PHOTOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0041967368     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-9801     Document Type: Article

References (37)

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25. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
26. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
27. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
28. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
29. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
30. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
31. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
32. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
33. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
34. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
35. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
36. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.
37. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15, 1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974, 96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975, 10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D. Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y. Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A. Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem., 1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med. Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S. Trifonov and A. S. Orahovats, Tetrahedron Lett., 1985, 26, 3159; L. Kovacs and P. Kerekes, Acta Chim. Hung., 1985, 120, 103; P. R. Huddleston, J. M. Barker, B. Stickland, M. L. Wood, and L. H. M. Guindi, J. Chem. Res. , 1988, 240; C. T. Goralski, R. C. Krauss, B. M. Williams, D. R. Henton, and D. T. Brown, Ind. Eng. Chem. Res., 1989, 28, 221; R. Hirsenkorn, Tetrahedron Lett., 1991, 32, 1775; R. Suau, R. Rico-Gomez, F. A. Souto-Bachiller, L. de los A. Rodriguez-Rodriguez, and M. L. Ruiz, Tetrahedron Lett., 1995, 36, 2653.