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Volumn 65, Issue 51, 2009, Pages 10650-10659

Synthesis of unsaturated 1,4-heteroatom-containing benzo-fused heterocycles using a sequential isomerization-ring-closing metathesis strategy

Author keywords

1,4 Benzodioxins; 1,4 Benzoxathiin; 4H 1,4 Benzoxazines; Benzodithiin; Isomerization; Ring closing metathesis

Indexed keywords

1,4 BENZODIOXIN DERIVATIVE; 1,4 BENZODITHIIN; 1,4 BENZOXATHIIN; 1,4 BENZOXAZINE DERIVATIVE; BENZENE DERIVATIVE; BENZOXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 70449515684     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.061     Document Type: Article
Times cited : (33)

References (95)
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    • For reviews see
    • For reviews see:
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    • Of interest is that a closely related compound purpurasol, the 5-demethoxy derivative of purpurenol, has also been isolated. A revised structure of this compound, concerning the substituted dioxane portion, has also been published and we thank a reviewer for pointing out this matter:
    • Of interest is that a closely related compound purpurasol, the 5-demethoxy derivative of purpurenol, has also been isolated. A revised structure of this compound, concerning the substituted dioxane portion, has also been published and we thank a reviewer for pointing out this matter:. Boeykens M., De Kimpe N., Debenedetti S.L., Nadinic E.L., Gomez M.A., Coussio J.D., Abyshev A.Z., and Gindin V.A. Phytochemistry 36 (1994) 1559-1560
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    • Boeykens, M.1    De Kimpe, N.2    Debenedetti, S.L.3    Nadinic, E.L.4    Gomez, M.A.5    Coussio, J.D.6    Abyshev, A.Z.7    Gindin, V.A.8
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    • See for example
    • See for example:
  • 27
    • 70449490562 scopus 로고    scopus 로고
    • For a list of recent reviews on RCM see:the following reference and reviews cited therein
    • For a list of recent reviews on RCM see:the following reference and reviews cited therein
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    • 70449499008 scopus 로고    scopus 로고
    • See, for example, the following recent papers and references cited therein
    • See, for example, the following recent papers and references cited therein:
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    • 70449499006 scopus 로고    scopus 로고
    • For an informative review exploring pre- and post-RCM-isomerization see
    • For an informative review exploring pre- and post-RCM-isomerization see:
  • 38
    • 70449464899 scopus 로고    scopus 로고
    • For a review on tandem processes involving methesis see
    • For a review on tandem processes involving methesis see:
  • 40
    • 70449476430 scopus 로고    scopus 로고
    • For reviews describing the metathesis of heteroatom-substituted olefins and examples relating to the metathesis of vinyl ethers, enamines and enamides and vinyl sulfides see
    • For reviews describing the metathesis of heteroatom-substituted olefins and examples relating to the metathesis of vinyl ethers, enamines and enamides and vinyl sulfides see:
  • 43
    • 70449492877 scopus 로고    scopus 로고
    • Experimental data provided from the work of the following students: PhD: Morgans, G. L.; MSc: Ngidi, E. L.; Madeley, L. G. Aderibigbe, B. A.; Honours project: Khanye, S. D.
    • Experimental data provided from the work of the following students: PhD: Morgans, G. L.; MSc: Ngidi, E. L.; Madeley, L. G. Aderibigbe, B. A.; Honours project: Khanye, S. D.
  • 44
    • 70449464898 scopus 로고    scopus 로고
    • For a communication see
    • For a communication see:
  • 48
    • 70449476431 scopus 로고    scopus 로고
    • For another approach involving the RCM of two aryl vinyloxy functionalities see
    • For another approach involving the RCM of two aryl vinyloxy functionalities see:
  • 50
    • 70449476427 scopus 로고    scopus 로고
    • See for example
    • See for example:
  • 55
    • 70449484403 scopus 로고    scopus 로고
    • For excellent reviews on transition metal catalyzed isomerizations see the next two references
    • For excellent reviews on transition metal catalyzed isomerizations see the next two references:
  • 61
    • 70449484401 scopus 로고    scopus 로고
    • note
    • 3 to facilitate comparison with the literature data.
  • 62
    • 70449464894 scopus 로고    scopus 로고
    • For recent representative examples describing an isomerization process followed by RCM and related papers see
    • For recent representative examples describing an isomerization process followed by RCM and related papers see:
  • 70
    • 70449490563 scopus 로고    scopus 로고
    • For an example involving the simultaneous use of catalysts 13 and 14 see
    • For an example involving the simultaneous use of catalysts 13 and 14 see:
  • 72
    • 70449478411 scopus 로고    scopus 로고
    • note
    • The synthesis of N-substituted 1,4-dihydroquinoxalines was also attempted, without success, applying this methodology (see next reference) and using the following amine protecting groups: Ts, Boc, COPh and COMe. In all cases the synthetic sequence was successful until the isomerization step, after which the metathesis reaction only provided recovered starting material.
  • 73
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    • For a communication see
    • For a communication see:
  • 75
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    • For an example where a benzoxazine was formed in a methylenation-RCM strategy in the presence of benzoquinone, see
    • For an example where a benzoxazine was formed in a methylenation-RCM strategy in the presence of benzoquinone, see:
  • 78
    • 70449504787 scopus 로고    scopus 로고
    • See for example
    • See for example:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.