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Volumn 73, Issue 17, 2008, Pages 6784-6792

Synthesis of heterocyclic analogues of epibatidine via 7-azabicyclo[2.2.1] hept-2-yl radical intermediates. 1. Intermolecular reactions

Author keywords

[No Author keywords available]

Indexed keywords

ARSENIC COMPOUNDS; CHEMICAL COMPOUNDS; CHEMICAL REACTIONS; CHEMICAL REACTIVITY; NANOSTRUCTURED MATERIALS;

EID: 51549099185     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8011094     Document Type: Article
Times cited : (11)

References (70)
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    • For some selected reviews on the chemistry and biology of epibatidine and analogues, see: a
    • For some selected reviews on the chemistry and biology of epibatidine and analogues, see: (a) Daly, J. W. J. Med. Chem. 2003, 46, 445.
    • (2003) J. Med. Chem , vol.46 , pp. 445
    • Daly, J.W.1
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    • Shen, T. Y.; Harman, W. D.; Huang, D. F.; González, J. US(1998)5817679.
    • (a) Shen, T. Y.; Harman, W. D.; Huang, D. F.; González, J. US(1998)5817679.
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    • Shen, T. Y.; Harman, W. D.; Huang, D. F.; González, J. WO1996 9606093.
    • (b) Shen, T. Y.; Harman, W. D.; Huang, D. F.; González, J. WO(1996 9606093.
  • 25
    • 51549101539 scopus 로고    scopus 로고
    • -1) shows that this process appears to be clearly unfavored and hardly achievable in the reaction conditions.
    • -1) shows that this process appears to be clearly unfavored and hardly achievable in the reaction conditions.
  • 28
    • 51549086857 scopus 로고    scopus 로고
    • 1N MR as the major product.
    • 1N MR as the major product.
  • 29
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    • Reference deleted in proof
    • Reference deleted in proof.
  • 35
    • 27944492386 scopus 로고    scopus 로고
    • 3, the reaction was incomplete and the yield of compound 7 was 12% (28%)].
    • 3, the reaction was incomplete and the yield of compound 7 was 12% (28%)].
  • 38
    • 51549085370 scopus 로고    scopus 로고
    • C-Br that reduces the interaction energy in the transition state.
    • C-Br that reduces the interaction energy in the transition state.
  • 41
    • 51549087054 scopus 로고    scopus 로고
    • See Supporting Information for etails
    • See Supporting Information for etails.
  • 51
    • 51549093289 scopus 로고    scopus 로고
    • A pioneering work by Schleyer focused attention on the relief of torsional strain involving the bridgehead CH bond in norbornyl systems and noted the general role of the transition-state torsional interactions: Schleyer, P. v. R. J. Am. Chem. Soc. 1967, 89, 701
    • A pioneering work by Schleyer focused attention on the relief of torsional strain involving the bridgehead CH bond in norbornyl systems and noted the general role of the transition-state torsional interactions: Schleyer, P. v. R. J. Am. Chem. Soc. 1967, 89, 701.
  • 61
    • 51549099922 scopus 로고    scopus 로고
    • We have also investigated the free radical allylation34 of bromide 1, a reaction that provided the expected 1-(2-allyl-7- azabicyclo[2.2.1]heptan-7-yl)-2,2,2-trifluoroethanone (16) in an incomplete and low yielding reaction see Supporting Information Available
    • 34 of bromide 1, a reaction that provided the expected 1-(2-allyl-7- azabicyclo[2.2.1]heptan-7-yl)-2,2,2-trifluoroethanone (16) in an incomplete and low yielding reaction (see Supporting Information Available).
  • 63
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    • Frisch, M. J. et al. Gaussian, Inc, Wallingford, CT
    • Gaussian 03, Revision B.03; Frisch, M. J. et al. Gaussian, Inc.: Wallingford, CT, 2003.
    • (2003) Gaussian 03, Revision B.03


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.