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Volumn 45, Issue 26, 2004, Pages 5057-5060

Protection of poorly nucleophilic pyrroles

Author keywords

Carbamate; Halogenation; Protecting groups; Pyrrole

Indexed keywords

PYRROLE DERIVATIVE; TETRABUTYLAMMONIUM;

EID: 2942615241     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.178     Document Type: Article
Times cited : (39)

References (18)
  • 1
    • 0037433940 scopus 로고    scopus 로고
    • The importance of these protecting groups in avoiding dehalogenation as a competing reaction has been reported earlier.
    • The importance of these protecting groups in avoiding dehalogenation as a competing reaction has been reported earlier. Handy S.T., Bregman H., Lewis J., Zhang Y. Tetrahedron Lett. 44:2003;427-430
    • (2003) Tetrahedron Lett. , vol.44 , pp. 427-430
    • Handy, S.T.1    Bregman, H.2    Lewis, J.3    Zhang, Y.4
  • 2
    • 2942526491 scopus 로고    scopus 로고
    • note
    • For example, treatment of methyl carbamate protected pyrrole-2- carboxaldehyde with NBS in a mixture of trifluoroacetic acid and sulfuric acid afforded 4, 5-dibromopyrrole-2-carboxaldehyde in which the carbamate group had been cleaved
  • 3
    • 0343570273 scopus 로고    scopus 로고
    • Protective Groups in Organic Synthesis
    • New York: John Wiley & Sons. pp 617-619
    • Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. 1999;John Wiley & Sons, New York. pp 617-619
    • (1999) 3rd Ed.
    • Greene, T.W.1    Wuts, P.G.M.2
  • 15
    • 2942526490 scopus 로고    scopus 로고
    • note
    • 4), filtered and concentrated in vacuo. The resultant residue was purified by flash chromatography. Elution with 1:5 ethyl acetate-hexane afforded 241.2 mg (72.6%) of 1 as a red solid
  • 16
    • 2942623176 scopus 로고    scopus 로고
    • note
    • 3, 90 MHz): δ 160.18, 128.04, 127.36, 107.03, 100.14, 51.40, 38.77; IR (neat) 3117, 2951, 1704, 1516, 1488, 1431, 1373, 1343, 1244, 1194, 1113, 1068, 956, 820, 759
  • 17
    • 2942597088 scopus 로고
    • A few isolated reports preparing iodoformates have appeared in the literature, including one that reports these to be more reactive versions of the corresponding chloroformates.
    • A few isolated reports preparing iodoformates have appeared in the literature, including one that reports these to be more reactive versions of the corresponding chloroformates. Hoffmann H.M.R., Iranshahi L. J. Org. Chem. 49:1984;1174-1176
    • (1984) J. Org. Chem. , vol.49 , pp. 1174-1176
    • Hoffmann, H.M.R.1    Iranshahi, L.2
  • 18
    • 0003795884 scopus 로고    scopus 로고
    • Y. Sasson, & R. Neuman. London: Blackie Academic & Professional
    • Sasson Y., Neuman R. Handbook of phase transfer catalysis. 1997;Blackie Academic & Professional, London
    • (1997) Handbook of Phase Transfer Catalysis


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.