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Volumn 64, Issue 11, 1999, Pages 4196-4198

Synthesis of 4-substituted 1-(benzyloxy)pyrazoles via iodine-magnesium exchange of 1-(benzyloxy)-4-iodopyrazole

Author keywords

[No Author keywords available]

Indexed keywords

1 (BENZYLOXY) 4 IODOPYRAZOLE; 1 (BENZYLOXY)PYRAZOLE DERIVATIVE; IODINE; MAGNESIUM; PALLADIUM; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ZINC CHLORIDE;

EID: 0033612361     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982160n     Document Type: Article
Times cited : (70)

References (34)
  • 5
    • 0344653487 scopus 로고    scopus 로고
    • note
    • 1H NMR.
  • 15
    • 0345084300 scopus 로고    scopus 로고
    • note
    • 16 See also ref 18.
  • 17
    • 0345515853 scopus 로고    scopus 로고
    • note
    • Attempts to generate 3 via oxidative addition of magnesium to 2 in THF failed.
  • 18
    • 0345084299 scopus 로고    scopus 로고
    • note
    • 1H NMR.
  • 19
    • 0345084298 scopus 로고    scopus 로고
    • note
    • Attempts to perform the iodine-lithium exchange with n-BuLi or t-BuLi (-78°C in THF) under conditions of reverse addition gave poor isolated yields (20-25%).
  • 21
    • 0345084296 scopus 로고    scopus 로고
    • note
    • 1H NMR of the crude product showed a 3:1 mixture of 4-benzoyl-1-(benzyloxy)pyrazole (4c) and 1-(benzyloxy)-4-(phenylhydroxymethyl)pyrazole (4b), as well as benzyl alcohol.
  • 26
    • 0032518829 scopus 로고    scopus 로고
    • For a review on cross-coupling reactions, see: Stanforth, S. P. Tetrahedron 1998, 54, 263.
    • (1998) Tetrahedron , vol.54 , pp. 263
    • Stanforth, S.P.1
  • 27
    • 0344222059 scopus 로고    scopus 로고
    • note
    • 1H NMR and showed 91% deuterium incorporation in the 4-position of 1-(benzyloxy)-pyrazole when 4-iodotoluene was used, whereas 1-(benzyloxy)pyrazole was the only observed product with 4-iodoaniline, indicating high basicity of 3.
  • 29
    • 0345084293 scopus 로고    scopus 로고
    • note
    • 4 (400 mL).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.