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Volumn 49, Issue 42, 2008, Pages 6134-6136

Synthesis and stereochemistry of 2-arylperhydrocyclopenta[b]pyridin-1-ols, 8-azaestrone fragments

Author keywords

[No Author keywords available]

Indexed keywords

1,5 DIKETONE DERIVATIVE; 8 AZAESTRONE; ACETIC ACID; ESTRONE DERIVATIVE; HYDROXYLAMINE; KETONE DERIVATIVE; OXIME DERIVATIVE; PERHYDROCYCLOPENTA[B]PYRIDINE 1 OL DERIVATIVE; PYRIDINE DERIVATIVE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

EID: 50549103450     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.020     Document Type: Article
Times cited : (6)

References (24)
  • 20
    • 50549083326 scopus 로고    scopus 로고
    • note
    • The mono-oximes 5a-c and 6a-b were prepared by stirring corresponding 1,5-diketones (1 equiv) with hydroxylamine hydrochloride (1 equiv), potassium acetate (2 equiv), and acetic acid in 1:1 ethanol water at reflux for 2-3.5 h. Yield = 61-77%.
  • 21
    • 50549096743 scopus 로고    scopus 로고
    • note
    • 4. The solvent was removed under reduced pressure and the crude product was subjected to column chromatography (silica gel 100-200 mesh, hexanes-EtOAc; 95:5-85:15) to obtain cyclic N-hydroxylamines. It is to be noted that the reaction needed to be conducted at THF reflux temperature, as at room temperature it was too slow. After 24 h at room temperature, starting oxime was still present to an extent of 40%.
  • 22
    • 50549090517 scopus 로고    scopus 로고
    • note
    • See Supplementary data for the NMR spectra, assignments, experimental procedure, and X-ray crystal structure diagrams. Crystallographic data for 2b and 4c have been deposited with the Cambridge Crystallographic Data Center as Supplementary Publication Nos. 2b: CCDC 671317 and 4c: CCDC 671318.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.