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Volumn 13, Issue 1, 2011, Pages 102-105

A practical, one-pot synthesis of sulfonylated pyridines

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE; SULFONE;

EID: 78650861142     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102629c     Document Type: Article
Times cited : (139)

References (45)
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    • US 4456469.
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    • Preparation of aryl and heteroaryl compounds having anti-retrovirus activity. WO 9206683.
    • Wassmundt, F. W. Preparation of aryl and heteroaryl compounds having anti-retrovirus activity. WO 9206683, 1992.
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    • For leading references, see
    • For leading references, see
  • 23
  • 34
    • 78650918240 scopus 로고    scopus 로고
    • Both commercially available sodium p -toluenesulfinate and sodium p -toluenesulfinate hydrate could be employed with equal success.
    • Both commercially available sodium p -toluenesulfinate and sodium p -toluenesulfinate hydrate could be employed with equal success.
  • 35
    • 78650853580 scopus 로고    scopus 로고
    • DMAc was found to be the superior solvent for this reaction; nonpolar aprotic solvents resulted in no reaction.
    • DMAc was found to be the superior solvent for this reaction; nonpolar aprotic solvents resulted in no reaction.
  • 36
  • 38
    • 78650868394 scopus 로고    scopus 로고
    • The solubility of sodium p -toluenesulfinate in DMAC at rt was measured to be 1.0 mg/mL and at 100 °C was 1.5 mg/mL by HPLC analysis.
    • The solubility of sodium p -toluenesulfinate in DMAC at rt was measured to be 1.0 mg/mL and at 100 °C was 1.5 mg/mL by HPLC analysis.
  • 39
    • 78650863250 scopus 로고    scopus 로고
    • 2Tol was completely soluble in DMAc at 100 °C.
    • 2Tol was completely soluble in DMAc at 100 °C.
  • 40
    • 78650877898 scopus 로고    scopus 로고
    • While protonation of sodium p -toluenesulfinate is a possibility in the presence of HCl, the fact that these reactions proceed to completion and in high yield suggest that protonation of the pyridine nitrogen is faster.
    • While protonation of sodium p -toluenesulfinate is a possibility in the presence of HCl, the fact that these reactions proceed to completion and in high yield suggest that protonation of the pyridine nitrogen is faster.
  • 41
    • 78650892975 scopus 로고    scopus 로고
    • 3-Bromopyridine, 3-fluoropyridine, and 3-iodopyridine also failed to react with sulfinate 2.
    • 3-Bromopyridine, 3-fluoropyridine, and 3-iodopyridine also failed to react with sulfinate 2.
  • 42
    • 78650856127 scopus 로고    scopus 로고
    • For the preparation of compound 26 under similar conditions, see
    • For the preparation of compound 26 under similar conditions, see
  • 45
    • 78650916687 scopus 로고    scopus 로고
    • Although not investigated in the present study, the methodology should be applicable to other types of alkyl and aryl sulfinate salts.
    • Although not investigated in the present study, the methodology should be applicable to other types of alkyl and aryl sulfinate salts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.