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Volumn 54, Issue 40, 1998, Pages 12361-12378

Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROPYRROLO[2,1 A]ISOQUINOLINONE; IMIDE; N PHENETHYLIMIDE; ORGANOLITHIUM COMPOUND; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032191024     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00745-5     Document Type: Article
Times cited : (43)

References (42)
  • 3
    • 0010400675 scopus 로고
    • and references cited therein
    • 3. Ashby, E. C.; Deshpande A. K. J. Org. Chem. 1995, 60, 4530, and references cited therein.
    • (1995) J. Org. Chem. , vol.60 , pp. 4530
    • Ashby, E.C.1    Deshpande, A.K.2
  • 5
    • 0030496093 scopus 로고    scopus 로고
    • 4. Yus, M.; Ramón, D. J. Chem. Soc. Chem. Commun. 1991, 398. For a review, see: Yus, M. Chem. Soc. Rev. 1996, 155.
    • (1996) Chem. Soc. Rev. , pp. 155
    • Yus, M.1
  • 6
    • 0010402689 scopus 로고    scopus 로고
    • 5. See, for instance: Bachki, A.; Fobuelo, F.; Yus, M. Tetrahedron 1997, 55, 4921; Almena, J.; Fobuelo, F.; Yus, M. J. Org. Chem. 1996, 61, 1859, and references cited therein.
    • (1997) Tetrahedron , vol.55 , pp. 4921
    • Bachki, A.1    Fobuelo, F.2    Yus, M.3
  • 7
    • 0001262307 scopus 로고    scopus 로고
    • and references cited therein
    • 5. See, for instance: Bachki, A.; Fobuelo, F.; Yus, M. Tetrahedron 1997, 55, 4921; Almena, J.; Fobuelo, F.; Yus, M. J. Org. Chem. 1996, 61, 1859, and references cited therein.
    • (1996) J. Org. Chem. , vol.61 , pp. 1859
    • Almena, J.1    Fobuelo, F.2    Yus, M.3
  • 14
    • 85038547485 scopus 로고    scopus 로고
    • Maleimide 4 was prepared by condensation of 2-(3,4-dimethoxyphenyl)ethylamine with maleic anhydride in refluxing acetic acid (yield 76%)
    • 9. Maleimide 4 was prepared by condensation of 2-(3,4-dimethoxyphenyl)ethylamine with maleic anhydride in refluxing acetic acid (yield 76%).
  • 15
    • 85038543848 scopus 로고    scopus 로고
    • To prove that the organolithium was only needed to initiate the polymerization proccess, maleimide 4 was treated with substoichiometric quantities of n-BuLi (0.1 eq, 0.25 eq), obtaining identical results
    • 10. To prove that the organolithium was only needed to initiate the polymerization proccess, maleimide 4 was treated with substoichiometric quantities of n-BuLi (0.1 eq, 0.25 eq), obtaining identical results.
  • 16
    • 84944048371 scopus 로고
    • Katritzsky, A. R.; Rees, C. W.; Meth-Cohn, O. Eds.; Pergamon Press: Oxford
    • 11. Heilmann, S. M.; Rasmussen, J. K. W. N. In Comprehensive Heterocydic Chemistry, Katritzsky, A. R.; Rees, C. W.; Meth-Cohn, O. Eds.; Pergamon Press: Oxford, 1984; vol. 1; p. 269.
    • (1984) Comprehensive Heterocydic Chemistry , vol.1 , pp. 269
    • Heilmann, S.M.1    Rasmussen, J.K.W.N.2
  • 25
    • 85038543392 scopus 로고    scopus 로고
    • Several reaction conditions were tested, but no extrusion of cyclopentadiene was detected at lower temperatures
    • 14. Several reaction conditions were tested, but no extrusion of cyclopentadiene was detected at lower temperatures.
  • 37
    • 85038551622 scopus 로고    scopus 로고
    • 17 was prepared by alkylation of thiophenol with 1,3-diodopropane. See experimental section
    • 20. 17 was prepared by alkylation of thiophenol with 1,3-diodopropane. See experimental section.
  • 38
    • 85038539780 scopus 로고    scopus 로고
    • Desilylation prior to cyclization was necessary. When the cyclization was carried out directly on 19a,b, dethioketalization occurred, loosing the desired functionality
    • 21. Desilylation prior to cyclization was necessary. When the cyclization was carried out directly on 19a,b, dethioketalization occurred, loosing the desired functionality.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.