Synthesis of tricyclic nitrogen-containing heterocycles by palladium-catalyzed cyclization of 2-alkenyl-N-(o-iodobenzoyl)-and 2-alkenyl-N-(o-iodophenylacetyl)-pyrrolidines

Heterocycles

Volumn 42, Issue 1, 1996, Pages 155-158

  Ikeda, Masazumi ^a   Akamatsu, Susumu ^a   Kugo, Yasuhiro ^a   Sato, Tatsunori ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012846683     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-S63     Document Type: Article

References (15)

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2. (b) M. Ikeda, M. Okano, K. Kosaka, M. Kido, and H. Ishibashi, Chem. Pharm. Bull., 1993, 41, 276;
3. (c) M. Ikeda, K. Matsubayashi, T. Imoto, K. Kitao, H. Ishibashi, and T. Sato, Heterocycles, 1994, 38, 1237.
4. T. Sato, Y. Kugo, and M. Ikeda, unpublished results.
5. T. Sato, T. Mori, T. Sugiyama, H. Ishibashi, and M. Ikeda, Heterocycles, 1994, 37, 245; T. Sato, Y. Kugo, E. Nakaumi, H. Ishibashi, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, in press.
6. T. Sato, T. Mori, T. Sugiyama, H. Ishibashi, and M. Ikeda, Heterocycles, 1994, 37, 245; T. Sato, Y. Kugo, E. Nakaumi, H. Ishibashi, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, in press.
7. R. F. Heck, "Palladium Reagents in Organic Synthesis," Academic Press, London, 1985; J. Tsuji, "Organic Synthesis with Palladium Compounds," Springer-Verlag, 1980; G. D. Daves and A. Hallberg, Chem. Rev., 1989, 89, 1433; R. Grigg, J. Heterocycl. Chem., 1994, 31, 631; W. Cabri and I. Candiani, Acc. Chem. Res., 1995, 28, 2; A. Ashimori, T. Matsuura, L. E. Overman, and D. J. Poon, J. Org. Chem., 1993, 58, 6949, and references cited therein; L. F. Tietze and O. Burkhardt, Synthesis, 1994, 1331.
8. R. F. Heck, "Palladium Reagents in Organic Synthesis," Academic Press, London, 1985; J. Tsuji, "Organic Synthesis with Palladium Compounds," Springer-Verlag, 1980; G. D. Daves and A. Hallberg, Chem. Rev., 1989, 89, 1433; R. Grigg, J. Heterocycl. Chem., 1994, 31, 631; W. Cabri and I. Candiani, Acc. Chem. Res., 1995, 28, 2; A. Ashimori, T. Matsuura, L. E. Overman, and D. J. Poon, J. Org. Chem., 1993, 58, 6949, and references cited therein; L. F. Tietze and O. Burkhardt, Synthesis, 1994, 1331.
9. R. F. Heck, "Palladium Reagents in Organic Synthesis," Academic Press, London, 1985; J. Tsuji, "Organic Synthesis with Palladium Compounds," Springer-Verlag, 1980; G. D. Daves and A. Hallberg, Chem. Rev., 1989, 89, 1433; R. Grigg, J. Heterocycl. Chem., 1994, 31, 631; W. Cabri and I. Candiani, Acc. Chem. Res., 1995, 28, 2; A. Ashimori, T. Matsuura, L. E. Overman, and D. J. Poon, J. Org. Chem., 1993, 58, 6949, and references cited therein; L. F. Tietze and O. Burkhardt, Synthesis, 1994, 1331.
10. R. F. Heck, "Palladium Reagents in Organic Synthesis," Academic Press, London, 1985; J. Tsuji, "Organic Synthesis with Palladium Compounds," Springer-Verlag, 1980; G. D. Daves and A. Hallberg, Chem. Rev., 1989, 89, 1433; R. Grigg, J. Heterocycl. Chem., 1994, 31, 631; W. Cabri and I. Candiani, Acc. Chem. Res., 1995, 28, 2; A. Ashimori, T. Matsuura, L. E. Overman, and D. J. Poon, J. Org. Chem., 1993, 58, 6949, and references cited therein; L. F. Tietze and O. Burkhardt, Synthesis, 1994, 1331.
11. R. F. Heck, "Palladium Reagents in Organic Synthesis," Academic Press, London, 1985; J. Tsuji, "Organic Synthesis with Palladium Compounds," Springer-Verlag, 1980; G. D. Daves and A. Hallberg, Chem. Rev., 1989, 89, 1433; R. Grigg, J. Heterocycl. Chem., 1994, 31, 631; W. Cabri and I. Candiani, Acc. Chem. Res., 1995, 28, 2; A. Ashimori, T. Matsuura, L. E. Overman, and D. J. Poon, J. Org. Chem., 1993, 58, 6949, and references cited therein; L. F. Tietze and O. Burkhardt, Synthesis, 1994, 1331.
12. R. F. Heck, "Palladium Reagents in Organic Synthesis," Academic Press, London, 1985; J. Tsuji, "Organic Synthesis with Palladium Compounds," Springer-Verlag, 1980; G. D. Daves and A. Hallberg, Chem. Rev., 1989, 89, 1433; R. Grigg, J. Heterocycl. Chem., 1994, 31, 631; W. Cabri and I. Candiani, Acc. Chem. Res., 1995, 28, 2; A. Ashimori, T. Matsuura, L. E. Overman, and D. J. Poon, J. Org. Chem., 1993, 58, 6949, and references cited therein; L. F. Tietze and O. Burkhardt, Synthesis, 1994, 1331.
13. R. F. Heck, "Palladium Reagents in Organic Synthesis," Academic Press, London, 1985; J. Tsuji, "Organic Synthesis with Palladium Compounds," Springer-Verlag, 1980; G. D. Daves and A. Hallberg, Chem. Rev., 1989, 89, 1433; R. Grigg, J. Heterocycl. Chem., 1994, 31, 631; W. Cabri and I. Candiani, Acc. Chem. Res., 1995, 28, 2; A. Ashimori, T. Matsuura, L. E. Overman, and D. J. Poon, J. Org. Chem., 1993, 58, 6949, and references cited therein; L. F. Tietze and O. Burkhardt, Synthesis, 1994, 1331.
14. The bromo analog of 7a also gave the same product (10a) but the cyclization reaction was very slow.
15. The Heck reaction of the piperidine (13a) and azetidine derivatives (13b), which were synthesized by alkylation of methyl N-(o-iodobenzoyl)piperidine-2-carboxylate and its azetidine congener with prop-2-enyl bromide, gave the octahydropyrido[1,2-b][2]benzazepin-6-one (14a), mp 54.5 °C, and the hexahydroazeto[1,2-b][2]benzazepin-4-one (14b), mp 119-120 °C, in 84 and 93% yields, respectively. chemical equations presented.