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Volumn 64, Issue 3, 1999, Pages 1007-1010

N-Azinylpyridinium N-aminides: Intermediates for the regioselective synthesis of 3-fluoro-2-aminopyridine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOPYRIDINE DERIVATIVE; DIAZONIUM COMPOUND; FLUORINE DERIVATIVE; PYRIDINIUM DERIVATIVE;

EID: 0001111464     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9813540     Document Type: Article
Times cited : (34)

References (31)
  • 8
    • 0014375025 scopus 로고
    • Saito, N.; Kurihara, T.; Yasuda, S.; Yamanaka, K.; Tsuruta, S.; Tanaka, T.; Inamori, Y. Yakugaku Zasshi 1968, 88, 1610; Chem. Abstr. 1969, 70, 87639.
    • (1969) Chem. Abstr. , vol.70 , pp. 87639
  • 22
    • 0344073416 scopus 로고    scopus 로고
    • note
    • f ≈ 0.6, silica gel, ethanol). On the other hand, fluorination of 2a with xenon difluoride does not provide the difluoro derivative compound, but only oxidized byproducts were observed. In this way, no fluorinated compounds were detected in the reaction with other aminides, as pyridlnium N-(pyrimidin-2′-yl)aminide.
  • 25
    • 0345366836 scopus 로고    scopus 로고
    • note
    • The negative charge on the exocyclic nitrogen facilates the reaction of the pyridine nucleus toward electrophiles. This ability is decreased for compounds 2a-e due to the high electronegativity of halogen atom in the 5-position. Lower yields for fluorination in 5-haloaminides could be partially attributed to this effect. On the other hand, coordination of the xenon difluoride to the halogen in 5-position could also be an undesirable effect, but some attempts of fluorination increasing concentration of xenon difluoride did produce complex mixtures.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.