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Volumn 65, Issue 17, 2000, Pages 5253-5263

A new germanium-based linker for solid phase synthesis of aromatics: Synthesis of a pyrazole library

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; AROMATIC COMPOUND; BIPHENYL DERIVATIVE; BROMINE; GERMANIUM; HYDRAZINE DERIVATIVE; IODINE DERIVATIVE; PHENOL DERIVATIVE; PYRAZOLE; RESIN;

EID: 0034714565     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000401x     Document Type: Article
Times cited : (66)

References (104)
  • 21
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    • PCT Int. Appl. WO 9744367 1997; p 36
    • Newlander, K. A.; Moore, M. L. In PCT Int. Appl. WO 9744367 1997; p 36.
    • Newlander, K.A.1    Moore, M.L.2
  • 42
    • 0343120251 scopus 로고    scopus 로고
    • note
    • Trichlorogermane/diethyl etherate complex decomposes rapidly in other solvents preventing its use in higher boiling solvents.
  • 50
    • 0343992298 scopus 로고    scopus 로고
    • note
    • Interestingly, 2-phenethyl chloride underwent dichlorogermylene insertion much more slowly giving 2-phenethyltrichlorogermane in just 16% yield after 16 h under identical conditions and lending credence to the involvement of neighboring group participation by the phenolic ring in reaction with chloride 1.
  • 52
    • 0343120248 scopus 로고    scopus 로고
    • note
    • 3 was employed, a trace of the corresponding dichlorogermanium oxide was also re-extracted.
  • 54
    • 0342685969 scopus 로고    scopus 로고
    • note
    • Commercially available from AFChemPharm Ltd., Unit C14, Alison Centre, Alison Cresent, Sheffield, S2 1AS, U.K.
  • 55
    • 0343120246 scopus 로고    scopus 로고
    • note
    • 67
  • 73
    • 0343992284 scopus 로고    scopus 로고
    • note
    • -1.
  • 90
    • 0343992282 scopus 로고    scopus 로고
    • note
    • 3 (5 mol %), KHMDS (2.2 equiv), toluene, 90 min, 110°C. Interestingly, reaction of soluble model 13 with 2-bromo toluene under these conditions led to the unexpected isolation of the corresponding 4-carboxylic acid derivative presumably as the result of a haloformtype reaction.
  • 93
    • 0343556124 scopus 로고    scopus 로고
    • note
    • 1,5-Diaryl substitution was confirmed by a single-crystal X-ray structure determination in this case. See Supporting Information.
  • 94
    • 0343992280 scopus 로고    scopus 로고
    • note
    • Interestingly, hydrazine salts invariably performed much better than the corresponding free hydrazines for pyrazole formation.
  • 95
    • 0343120236 scopus 로고    scopus 로고
    • note
    • Purity is based on area/area integration of HPLC peaks (220 nm detection) with no correction for response factors.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.