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Volumn , Issue 14, 2006, Pages 2339-2341

Convenient access to 2-arylpyrroles from 2-lithio-N,N- dibenzylcyclopropylamine and nitriles

Author keywords

2 arylpyrroles; Cyclopropylamines; Donor acceptor substituted cyclopropanes; Nitriles; Tin lithium exchange

Indexed keywords

2 ARYLPYRROLE DERIVATIVE; 2 LITHIO N,N DIBENZYLCYCLOPROPYLAMINE; CYCLOPROPANE DERIVATIVE; DIBENZYLAMINE; N,N DIBENZYLAMINOCYCLOPROPYL KETIMINE DERIVATIVE; NITRILE; PROPYLAMINE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33748708191     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950410     Document Type: Article
Times cited : (15)

References (36)
  • 4
    • 0034806165 scopus 로고    scopus 로고
    • and references cited therein
    • The well-known vinylcyclopropane-to-cyclopentene rearrangement is significantly accelerated by donor substituents like alkoxy and dialkylamino groups in the 2-position; compare with: (a) McGaffin, G.; Grimm, B.; Heinecke, U.; Michaelsen, H.; de Meijere, A.; Walsh, R. Eur. J. Org. Chem. 2001, 3559; and references cited therein,
    • (2001) Eur. J. Org. Chem. , pp. 3559
    • McGaffin, G.1    Grimm, B.2    Heinecke, U.3    Michaelsen, H.4    De Meijere, A.5    Walsh, R.6
  • 6
    • 0012974554 scopus 로고
    • The rearrangement of cyclopropylketimines, which is catalyzed by acids and known as the Cloke rearrangement, should also be accelerated by donor substituents: (a) Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174.
    • (1929) J. Am. Chem. Soc. , vol.51 , pp. 1174
    • Cloke, J.B.1
  • 9
    • 0039354995 scopus 로고    scopus 로고
    • Carbocyclic three-and four-membered ring compounds
    • de Meijere, A., Ed.; Thieme: Stuttgart
    • For reviews on vicinally donor-acceptor-substituted cyclopropanes see: (a) von Angerer, S. Carbocyclic Three-and Four-Membered Ring Compounds, In Methods of Organic Chemistry, Houben-Weyl, Vol. 17c; de Meijere, A., Ed.; Thieme: Stuttgart, 1997, 2121.
    • (1997) Methods of Organic Chemistry, Houben-Weyl , vol.17 C , pp. 2121
    • Von Angerer, S.1
  • 16
    • 33748694435 scopus 로고    scopus 로고
    • Angew. Chem. 2004, 116, 2723.
    • (2004) Angew. Chem. , vol.116 , pp. 2723
  • 23
    • 0001539554 scopus 로고
    • The conversion of 3-oxoketimines into 2-hydroxy-5-arylpyrrolines has been reported, see: Chiu, P.-K.; Sammes, M. P. Tetrahedron 1988, 44, 3531.
    • (1988) Tetrahedron , vol.44 , pp. 3531
    • Chiu, P.-K.1    Sammes, M.P.2
  • 25
    • 33748708335 scopus 로고    scopus 로고
    • note
    • 4, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel (PE-EtOAc, 9:1).
  • 26
    • 33748707295 scopus 로고    scopus 로고
    • note
    • 13C NMR
  • 27
    • 33748699921 scopus 로고    scopus 로고
    • note
    • +; found: 174.0918.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.