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Volumn 68, Issue 2, 2003, Pages 644-647

An efficient assembly of heterobenzazepine ring systems utilizing an intramolecular palladium-catalyzed cycloamination

Author keywords

[No Author keywords available]

Indexed keywords

RING SYSTEMS;

EID: 0037462378     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026546g     Document Type: Article
Times cited : (61)

References (29)
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    • Participant in Pharmacia Corporation's Summer Intern Program
    • Participant in Pharmacia Corporation's Summer Intern Program.
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    • For reviews of palladium-catalyzed aminations see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-18. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 204-667. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146. (d) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Cross-Coupling Reaction: A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry Ser. 219; Springer-Verlag: New York, NY, 2002; pp 131-209.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 805-818
    • Wolfe, J.P.1    Wagaw, S.2    Marcoux, J.-F.3    Buchwald, S.L.4
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    • For reviews of palladium-catalyzed aminations see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-18. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 204-667. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146. (d) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Cross-Coupling Reaction: A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry Ser. 219; Springer-Verlag: New York, NY, 2002; pp 131-209.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 204-667
    • Hartwig, J.F.1
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    • For reviews of palladium-catalyzed aminations see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-18. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 204-667. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146. (d) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Cross-Coupling Reaction: A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry Ser. 219; Springer-Verlag: New York, NY, 2002; pp 131-209.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 125-146
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    • Practical palladium catalysts for C-N and C-O bond formation
    • Miyaura, N., Ed.; Topics in Current Chemistry Ser. 219; Springer-Verlag: New York, NY
    • For reviews of palladium-catalyzed aminations see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-18. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 204-667. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146. (d) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Cross-Coupling Reaction: A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry Ser. 219; Springer-Verlag: New York, NY, 2002; pp 131-209.
    • (2002) Cross-Coupling Reaction: A Practical Guide , pp. 131-209
    • Muci, A.R.1    Buchwald, S.L.2
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    • Although there are examples in the literature where a sulfur or oxygen atom α to the site of insertion is a successful transformation, in our substrate these attempts provided only decomposition products and no tricyclic product. Link, J. T.; Sorensen, B.; Liu, G.; Pei, Z.; Reilly, E. B.; Leitza, S.; Okasinki, G. Bioorg. Med. Chem. Lett. 2001, 11, 973-6.
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    • Link, J.T.1    Sorensen, B.2    Liu, G.3    Pei, Z.4    Reilly, E.B.5    Leitza, S.6    Okasinki, G.7
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    • note
    • The yield for the transformation of 7h to 4h by the 3-step method of Yale (see ref 6c) was 54%.
  • 20
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    • note
    • The phosphine sources included di-tert-butylphosphinobiphenyl, BINAP, P(t-Bu)3, and dicyclohexylphosphinobiphenyl.
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    • note
    • For an expanded version of Table 1 with details of the optimization, see the Supporting Information.
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    • note
    • The yield for the transformation of 7c to 4c by the 3-step method of Yale (see the tables for yields in ref 6a) was 40%.
  • 29
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    • note
    • For general experimental considerations see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.