Syntheses of Medium-sized Ring Amines from Bicyclic Amines Yoshio ARATA* and Miyoji HANAOKA** Conversion of bicyclic amines into medium-sized ring ami
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1 Syntheses of Medium-sized Ring Amines from Bicyclic Amines Yoshio ARATA* and Miyoji HANAOKA** Conversion of bicyclic amines into medium-sized ring amines (tertiary and secondary) by selective cleavage of C-N or C-C bond is reviewed. The effectiveness of 9a- or 8a-substituents on quinolizidines or indolizidines in the above conversion is described. Fig. 2 Fig. 1 School of Pharmacy, Hokuriku University I) Faculty of Pharmaceutical Sciences, Kanazawa University )
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4 (30) R=CN,X=I (31) R=CONH21X=Br (32) R'=H (33) RI=CN (34) R'=CONH2 (35) (36) (37) (39) (40) (38) (41) (42) (43) (47) (44) (48) (49) (45) R=H2 (46) R=0
5 (56)R=CN (58)R=CO2Et (57)R=CN (59)R=CO2Et
6 (75) R=H (76) R=CH2Ph (77) R=H (78) R=CH2Ph (79) R=H (80) R=CH2Ph
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9 (122) (124) (121a)R1=H,R2=Me (121b)12.1=NO2,R2=Me (121c)R1=H,R2=Ac (123) (125) (128) (130) (126)R=H (127) R=Me (129) (131) (132a) (132b) (133a) (133b) (134a) (134b) (135) (136) (137) (138) (139)
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11 (159) (160a) R=Et (160b)R=H Fig. 28 (166a) (166b) (167a) (167b) Fig. 30 (168a) (168b) (161a) (161b) (162a) (162b) (163) (164) (165) Fig. 29 (169) (170) (171) (172) (174) (173) Fig. 31
12 (187) (188) (173) (189) Fig. 34 (190) (177) (178) (179) (180) (181) Fig. 32 Fig. 35 (182) (184) Fig. 33 (186) Fig. 36
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14 1) Y. Arata, Y. Oda, Chem. Pharm. Bull., 21, 752 (1973) 2) K.W. Bentley, A.W. Murray, J. Chem. Soc., 1963, ) Y. Arata, T. Shioda, Chem. Pharm. Bull., 20, 783 (1972) 5) Y. Arata, S. Yoshifuji, Y. Yasuda, ibid., 11, 1363 (1969) 6) Y. Arata, M. Takahashi, T. Aoki, ibid., 22, 1003 (1974) 7) Y. Arata, Y. Nakagawa, ibid., 21, 1248 (1973) 8) H. Kato, E. Koshinaka, Y. Arata, M. Hanaoka, ibid., 21, 2661 (1973) 9) H. Kato, E. Koshinaka, Y. Arata, M. Hanaoka, ibid., 21, 2039 (1973) 12) Y. Arata, M. Hanaoka, H. Kato, E. Koshinaka, T. Nishikawa, Chem. Pharm. Bull., 23, 2381 (1975) 13) K. Sugimoto, K. Ohme, M. Akiba, S. Ohki, ibid., 18, 1273 (1970) 14) M.G. Reinecke, L.R. Kray, R.F. Francis, J. Org. Chem., 37, 3489 (1972) 15) M.G. Reinecke, L.R. Kray, R.F. Francis, Tetrahedron Lett., 1965, ) Y. Arata, S. Yasuda, K. Tokuno, M. Hanaoka, Chem. Pharm. Bull., 24, 1879 (1976) 17) N. Finch, C.W. Gemenden, J. Org. Chem., 38, 437 (1973) 18) P. Aeberli, W.J. Houlihan, ibid., 34, 2715 (1969) 19) Y. Arata, Y. Oda, S. Yasuda, M. Hanaoka, Chem. Pharm. Bull., 21, 2697 (1973) 20a) R.D. Haworth, W.H. Perkin, Jr., J. Chem. Soc., 1926, 445 b) R.D. Haworth, W.H. Perkin, Jr., ibid., 1926, 1769 c) R.D. Haworth, J.B. Koepfli, W.H. Perkin, Jr., ibid., 1927, ) M.G. Reinecke, R.F. Francis, J. Org. Chem., 37, 3494 (1972) 22) M. Winn, H.E. Zaugg, ibid., 33, 3779 (1968) 23) W. Nagata, K. Okada, H. Itazaki, S. Uyeo, Chem. Pharm. Bull., 23, 2878 (1975) 24) L.J. Dolby, D.L. Booth, J. Org. Chem., 30, 1550 (1965) 25a) L.J. Dolby, S. Sakai.,J. Am. Chem. 'Soc., 86, 1890 (1964) b) L.J. Dolby, S. Sakai, Tetrahedron, 23, 1 (1967) 26) M. Hanaoka, C. Mukai, Y. Arata, Heterocycles, 4, 1685 (1976) 27) B. Nalliah, R.H.F. Manske, R. Rodrigo, Tetrahedron Lett., 1974, ) I. Saito, M. Imuta, T. Matsuura, Chem. Lett., 1972, ) M. Nakagawa, Y. Okajima, K. Kobayashi, T. Asaka, T. Hino, Heterocycles, 3, 799 (1975) 31) J. Harly-Mason, A. Rahman, J. Chem. Soc., Chem. Commun., 1967, ) G.H. Foster, J. Harly-Mason, W.R. Waterfield, ibid., 1968, ) L.J. Dolby, S. Sakai, J. Am. Chem. Soc., 86, 5362 (1964) 34) L.J. Dolby, G.W. Gribble, J. Org. Chem., 32, 1391 (1967) 35) J.A. Marshall, G.L. Bundy, J. Chen. Soc., Chem. Commun., 1957, ) J.A. Marshall, J.H. Babler, J. Org. Chem., 34, 4186 (1969) 37) C.A. Grob, H.R. Kiefef, H.J. Lutz, H.J. Wilkens, Hely. Chim. Acta, 50, 416 (1967) 38a) C.A. Grob, P.W. Schiess, Angew. Chem., 79, 1 (1967) b) C.A. Grob, ibid., 81, 543 (1969) 39) J.D. Albright, L. Goldmann, J. Am. Chem. Soc., 91, 4317 (1969) 40) H. Ronsch, J. Prakt. Chem., 1972, ) J.P. Yardley, R.W. Ress, H. Smith, J. Med. Chem., 10, 1088 (1967) 43) M.G. Reinecke, R.G. Daubert, J. Org. Chem., 38, 3281 (1973) 44) N.J. Leonard, S. Swann, Jr., H.L. Dryden, Jr., J. Am. Chem. Soc., 74, 2871 (1952) 45) N.J. Leonard, S. Swann, Jr., J. Figueras, Jr., ibid., 74, 4620 (1952) 46) T.S. Sulkowski, M.A. Wille, A. Mascitti, J.L. Diebold, J. Org. Chem., 32, 2180 (1967) 47) P. Aeberli, W.J. Haulihan, ibid., 34, 1720 (1969) 48) V.L. Tweedie, J.C. Allabashi, ibid., 26, 3676
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