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Volumn 51, Issue 42, 2010, Pages 5516-5520

First synthesis of 2-phosphonylated quinoxaline 1,4-dioxides: An extension to the Beirut reaction

Author keywords

Beirut reaction; Molecular sieves; Phosphonate; Quinoxaline; Quinoxaline 1,4 dioxide

Indexed keywords

QUINOXALINE 1,4 DIOXIDE DERIVATIVE; QUINOXALINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

EID: 77956650963     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.148     Document Type: Article
Times cited : (14)

References (31)
  • 20
    • 77956648935 scopus 로고    scopus 로고
    • note
    • 5P, 374.1032, found 374.1024.
  • 22
    • 77956652669 scopus 로고    scopus 로고
    • On treating 2-chloroquinoxaline monoxide with an excess of CsF and [18:6] crown ether in THF at room temperature for 16 h, we obtained a crude mixture containing about 50% of the quite unstable 2-fluoroquinoxaline monoxide
    • On treating 2-chloroquinoxaline monoxide with an excess of CsF and [18:6] crown ether in THF at room temperature for 16 h, we obtained a crude mixture containing about 50% of the quite unstable 2-fluoroquinoxaline monoxide.
  • 23
    • 77956647743 scopus 로고    scopus 로고
    • Experiments run without adding HI resulted in no conversion into 2-iodoquinoxaline monoxide. This latter compound has already been prepared, albeit in lower yield, by thermal decomposition of the corresponding 2-diazonium fluoroborate (Balz-Schiemann reaction)
    • Experiments run without adding HI resulted in no conversion into 2-iodoquinoxaline monoxide. This latter compound has already been prepared, albeit in lower yield, by thermal decomposition of the corresponding 2-diazonium fluoroborate (Balz-Schiemann reaction).
  • 24
    • 50449107901 scopus 로고    scopus 로고
    • 2/dppf, as recently precognized for the synthesis of heteroarylphosphonates by Hirao cross-coupling: Y. Belabassi, S. Alzghari, and J.-L. Montchamp J. Organomet. Chem. 693 2008 3171 3178 Switching dppf to xantphos doubled the yield of the reaction
    • (2008) J. Organomet. Chem. , vol.693 , pp. 3171-3178
    • Belabassi, Y.1    Alzghari, S.2    Montchamp, J.-L.3
  • 29
    • 77956652834 scopus 로고    scopus 로고
    • Subjecting phosphonate 13a to treatment in methanol in the presence of molecular sieves under reaction conditions yielded a complete conversion into 2-methyl-quinoxaline 1,4-di-N-oxide 12
    • Subjecting phosphonate 13a to treatment in methanol in the presence of molecular sieves under reaction conditions yielded a complete conversion into 2-methyl-quinoxaline 1,4-di-N-oxide 12.
  • 30
    • 77956651467 scopus 로고    scopus 로고
    • 3, or MeOH
    • 3, or MeOH.
  • 31
    • 77956650331 scopus 로고    scopus 로고
    • The reaction appeared quite sluggish in the case of R = iPr or cyclopropyl: we observed in NMR on prolonged reaction time a complex mixture containing less than 15% of the desired phosphonate
    • The reaction appeared quite sluggish in the case of R = iPr or cyclopropyl: we observed in NMR on prolonged reaction time a complex mixture containing less than 15% of the desired phosphonate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.