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Volumn 45, Issue 12, 2004, Pages 2579-2583

The sequel to a carbocyclic nucleoside synthesis: A divergent access to both arenediazonium ions and aryl triflates

Author keywords

Aryl triflate; Carbocyclic nucleosides; Diazo coupling; Diazonium triflate; Diazotisation; Triazene

Indexed keywords

ARISTEROMYCIN; CARBOCYCLIC NUCLEOSIDE; DIAZONIUM COMPOUND; IODIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

EID: 1542302444     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.147     Document Type: Article
Times cited : (16)

References (55)
  • 10
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    • and cited references
    • Ha S.B., Nair V. Tetrahedron Lett. 37:1996;1567-1570. and cited references.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1567-1570
    • Ha, S.B.1    Nair, V.2
  • 12
    • 1542317301 scopus 로고    scopus 로고
    • note
    • 3): 531 (M+1), 405, 169.
  • 13
    • 1542377163 scopus 로고    scopus 로고
    • note
    • Thanks are due to Aventis Pharma Dévelopement (Vitry-sur-Seine) and Rhodia (Saint-Fons) for support. Drs. M. Mulhauser (from Aventis), L. Saint-Jalmes and J.-M Paris (from Rhodia) are acknowledged for a generous gift of the amine 2 and triflic acid, respectively, and their interest. These results are taken in part from the thesis and DEA dissertation of C. P. (Strasbourg, 2003) and F.W. (Strasbourg 2001), respectively.
  • 15
    • 33845556557 scopus 로고
    • Conversion of the triazene into a 6-halo compound would also have been possible: (a)
    • Conversion of the triazene into a 6-halo compound would also have been possible: (a) Ku H., Barrio J.R. J. Org. Chem. 46:1981;5239-5241.
    • (1981) J. Org. Chem. , vol.46 , pp. 5239-5241
    • Ku, H.1    Barrio, J.R.2
  • 40
    • 1542347420 scopus 로고
    • For an access to o-trifloxy-arenediazonium triflates from aromatic diazoketones (and their coupling reaction with phenols), see:
    • For an access to o-trifloxy-arenediazonium triflates from aromatic diazoketones (and their coupling reaction with phenols), see: Maas G., Tretter A. Liebigs Ann. Chem. 1985;1866-1873.
    • (1985) Liebigs Ann. Chem. , pp. 1866-1873
    • Maas, G.1    Tretter, A.2
  • 42
    • 1542317303 scopus 로고    scopus 로고
    • note
    • 2, owing to the poor solubility of 3d in AcOEt) was followed by crystallisation of the resulting syrup from an acetone/ether mixture to give the triflate 4d as a crystalline solid (82%). As previously noticed, the thermal stability of these arenediazonium triflates is remarkable. Thus brief heating of a small amount (ca. 100 mg) of the nitro derivative 4d to 100-110°C (oil bath) failed to induce any change on the basis of NMR analysis.
  • 43
    • 0027180141 scopus 로고    scopus 로고
    • note
    • 18 and by NMR, TLC and GLC analyses. For a review on aryl triflates, see: Ritter K. Synthesis. 1993;735-762.
  • 48
    • 1542347413 scopus 로고    scopus 로고
    • note
    • We acknowledge Mr. G. Médard for his contribution to this work, especially for exploratory experiments on the use of these anhydrous diazo-coupling conditions for colouring lipophilic materials.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.