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Volumn 11, Issue 7, 2009, Pages 1603-1606

A concise and versatile synthesis of viridicatin alkaloids from cyanoacetanilides

Author keywords

[No Author keywords available]

Indexed keywords

4 CYANOACETANILIDE; 4-CYANOACETANILIDE; ACETANILIDE DERIVATIVE; ALKALOID; QUINOLINOL DERIVATIVE; VIRIDICATIN;

EID: 64349096396     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900255g     Document Type: Article
Times cited : (81)

References (45)
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    • U. S. Patent 5, 892, 045
    • Sit, S.-Y.; Meanwell, N. A. U. S. Patent 5, 892, 045, 1999.
    • (1999)
    • Sit, S.-Y.1    Meanwell, N.A.2
  • 21
    • 0003151465 scopus 로고
    • The Friedlander Synthesis of Quinolines
    • For a review, see:, Dauben, W. C, Ed, J. Wiley and Sons: New York
    • (a) For a review, see: Cheng, C.-C.; Yan, S.-J. The Friedlander Synthesis of Quinolines. In Organic Reactions; Dauben, W. C., Ed.; J. Wiley and Sons: New York, 1982; Vol. 28, p 37.
    • (1982) Organic Reactions , vol.28 , pp. 37
    • Cheng, C.-C.1    Yan, S.-J.2
  • 25
    • 64349095096 scopus 로고    scopus 로고
    • Cyanoacetanilides (7a-f) were prepared by reacting cyanoacetic acid with the corresponding aniline up to a 20-g scale (77-96% yields). For experimental details, see the Supporting Information.
    • Cyanoacetanilides (7a-f) were prepared by reacting cyanoacetic acid with the corresponding aniline up to a 20-g scale (77-96% yields). For experimental details, see the Supporting Information.
  • 26
    • 64349089347 scopus 로고    scopus 로고
    • All spectral data were in full accord with those reported in the literature; see the Supporting Information
    • All spectral data were in full accord with those reported in the literature; see the Supporting Information.
  • 27
    • 0001586671 scopus 로고
    • For reviews of Friedel-Crafts and related reactions, see: a, Trost, B. M, Fleming I, Eds, Pergamon: Oxford, Chapter 1.8
    • For reviews of Friedel-Crafts and related reactions, see: (a) Olah, G. A.; Krishnamurti, R.; Prakash, G. S. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 1.8.
    • (1991) Comprehensive Organic Synthesis , vol.3
    • Olah, G.A.1    Krishnamurti, R.2    Prakash, G.S.S.3
  • 30
    • 84952096388 scopus 로고
    • For recent examples, see: For a review of epoxide-arene cyclizations, see: a
    • For a review of epoxide-arene cyclizations, see: (a) Taylor, S. K. Org. Prep. Proced. Int. 1992, 24, 245. For recent examples, see:
    • (1992) Org. Prep. Proced. Int , vol.24 , pp. 245
    • Taylor, S.K.1
  • 39
    • 64349109768 scopus 로고    scopus 로고
    • 2 was used as the oxidant instead of t-BuOOH, we observed partial hydrolysis of the CN group of 9aa.
    • 2 was used as the oxidant instead of t-BuOOH, we observed partial hydrolysis of the CN group of 9aa.
  • 40
    • 64349113690 scopus 로고    scopus 로고
    • Note that a tertiary anilide must be used to ensure a smooth annulation reaction. This is because the reaction of the secondary anilide (R1 = H) does not proceed at all, most probably due to conformational reasons; see: (a) Pederson, B. F.; Pederson, B. Tetrahedron Lett. 1965, 2995.
    • Note that a tertiary anilide must be used to ensure a smooth annulation reaction. This is because the reaction of the secondary anilide (R1 = H) does not proceed at all, most probably due to conformational reasons; see: (a) Pederson, B. F.; Pederson, B. Tetrahedron Lett. 1965, 2995.
  • 43
    • 0036857568 scopus 로고    scopus 로고
    • The term telescoping has been used before to describe sequential multistep/multipot processes with shortened or omitted isolation procedures for the involved intermediates; see, e.g.: Dale, D. J.; Draper, J.; Dunn, P. J.; Hughes, M. L.; Hussain, F.; Levett, P. C.; Ward, G. B.; Wood, A. S. Org. Process Res. Dev. 2002, 6, 767.
    • The term "telescoping" has been used before to describe sequential multistep/multipot processes with shortened or omitted isolation procedures for the involved intermediates; see, e.g.: Dale, D. J.; Draper, J.; Dunn, P. J.; Hughes, M. L.; Hussain, F.; Levett, P. C.; Ward, G. B.; Wood, A. S. Org. Process Res. Dev. 2002, 6, 767.
  • 44


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.