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Volumn 61, Issue 7, 1996, Pages 2273-2282

Preparation and 1,3-dipolar cycloaddition reactions of β-carboline azomethine ylides: A direct entry into C-1- and/or C-2-functionalized indolizino[8,7-b]indole derivatives

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; INDOLIZINE DERIVATIVE; INDOLIZINO[8,7 B]INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0029926693     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951520t     Document Type: Article
Times cited : (71)

References (58)
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    • G.P. and M.-H.T.-B. contributed equally to the synthetic work presented in this paper
    • G.P. and M.-H.T.-B. contributed equally to the synthetic work presented in this paper.
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    • For examples of nonregioselective cycloaddition reactions of azomethine ylides, see: (a) Achiwa, K.; Imai, N.; Motoyama, T ; Sekiya, M. Chem. Lett. 1984, 2041. (b) Terao, Y.; Kotaki, H.; Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896. (c) Imai, N.; Terao, Y.; Achiwa, K. Heterocycles 1985, 23, 1107. (d) Imai, N.; Terao, Y.; Achiwa, K. Chem. Pharm Bull. 1987, 35, 2085. (e) Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1987, 35, 2646. (f) Imai, N.; Tokiwa, H.; Akahori, Y.; Achiwa, K. Chem. Lett. 1986, 1113, as well as refs 15a, 16a, 23, and 27.
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    • For examples of nonregioselective cycloaddition reactions of azomethine ylides, see: (a) Achiwa, K.; Imai, N.; Motoyama, T ; Sekiya, M. Chem. Lett. 1984, 2041. (b) Terao, Y.; Kotaki, H.; Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896. (c) Imai, N.; Terao, Y.; Achiwa, K. Heterocycles 1985, 23, 1107. (d) Imai, N.; Terao, Y.; Achiwa, K. Chem. Pharm Bull. 1987, 35, 2085. (e) Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1987, 35, 2646. (f) Imai, N.; Tokiwa, H.; Akahori, Y.; Achiwa, K. Chem. Lett. 1986, 1113, as well as refs 15a, 16a, 23, and 27.
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    • For examples of nonregioselective cycloaddition reactions of azomethine ylides, see: (a) Achiwa, K.; Imai, N.; Motoyama, T ; Sekiya, M. Chem. Lett. 1984, 2041. (b) Terao, Y.; Kotaki, H.; Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896. (c) Imai, N.; Terao, Y.; Achiwa, K. Heterocycles 1985, 23, 1107. (d) Imai, N.; Terao, Y.; Achiwa, K. Chem. Pharm Bull. 1987, 35, 2085. (e) Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1987, 35, 2646. (f) Imai, N.; Tokiwa, H.; Akahori, Y.; Achiwa, K. Chem. Lett. 1986, 1113, as well as refs 15a, 16a, 23, and 27.
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    • For examples of nonregioselective cycloaddition reactions of azomethine ylides, see: (a) Achiwa, K.; Imai, N.; Motoyama, T ; Sekiya, M. Chem. Lett. 1984, 2041. (b) Terao, Y.; Kotaki, H.; Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896. (c) Imai, N.; Terao, Y.; Achiwa, K. Heterocycles 1985, 23, 1107. (d) Imai, N.; Terao, Y.; Achiwa, K. Chem. Pharm Bull. 1987, 35, 2085. (e) Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1987, 35, 2646. (f) Imai, N.; Tokiwa, H.; Akahori, Y.; Achiwa, K. Chem. Lett. 1986, 1113, as well as refs 15a, 16a, 23, and 27.
    • (1987) Chem. Pharm. Bull. , vol.35 , pp. 2646
    • Imai, N.1    Achiwa, K.2
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    • For examples of nonregioselective cycloaddition reactions of azomethine ylides, see: (a) Achiwa, K.; Imai, N.; Motoyama, T ; Sekiya, M. Chem. Lett. 1984, 2041. (b) Terao, Y.; Kotaki, H.; Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896. (c) Imai, N.; Terao, Y.; Achiwa, K. Heterocycles 1985, 23, 1107. (d) Imai, N.; Terao, Y.; Achiwa, K. Chem. Pharm Bull. 1987, 35, 2085. (e) Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1987, 35, 2646. (f) Imai, N.; Tokiwa, H.; Akahori, Y.; Achiwa, K. Chem. Lett. 1986, 1113, as well as refs 15a, 16a, 23, and 27.
    • (1986) Chem. Lett. , pp. 1113
    • Imai, N.1    Tokiwa, H.2    Akahori, Y.3    Achiwa, K.4
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    • 1H NMR data published for similarly substituted pyrrolidine compounds. For examples, see refs 21, 23, 24, and 31d as well as: (a) Bende, Z.; Toke, L.; Weber, L.; Toth, G.; Janke, P.; Csonka, G. Tetrahedron 1984, 40, 369. (b) Toth, G.; Frank, J.; Bende, Z.; Weber, L.; Simon, K. J. Chem. Soc., Perkin, Trans. 1 1983, 1961.
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    • 1H NMR data published for similarly substituted pyrrolidine compounds. For examples, see refs 21, 23, 24, and 31d as well as: (a) Bende, Z.; Toke, L.; Weber, L.; Toth, G.; Janke, P.; Csonka, G. Tetrahedron 1984, 40, 369. (b) Toth, G.; Frank, J.; Bende, Z.; Weber, L.; Simon, K. J. Chem. Soc., Perkin, Trans. 1 1983, 1961.
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    • Toth, G.1    Frank, J.2    Bende, Z.3    Weber, L.4    Simon, K.5
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    • 13C NMR has been shown to be a reliable method of determining cis/trans geometries in the cyclopentane series. See: Chin, I. C., Kohn, H. J. Org. Chem. 1983, 48, 2857.
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    • The relative configurations of H-11b and H-2 for all the C-2-substituted compounds of Scheme 10 were determined by performing NOE experiments
    • The relative configurations of H-11b and H-2 for all the C-2-substituted compounds of Scheme 10 were determined by performing NOE experiments.


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