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Volumn 62, Issue , 2004, Pages 757-772

Reactions of 2-, 3- and 4-quinolinols with cyclohexane and benzene in superacids

Author keywords

[No Author keywords available]

Indexed keywords

3 QUINOLINOL; 4 QUINOLINOL; ALUMINUM CHLORIDE; ALUMINUM DERIVATIVE; BENZENE; CARBOSTYRIL; CYCLOHEXANE; QUINOLINOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0347720665     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (40)

References (39)
  • 8
    • 0012733397 scopus 로고
    • For a low-temperature generation of substituted ethylene dications bearing electron-donating groups such as an aryl, a hydroxy, a methoxy and a N,N-dihydroxyamino groups or for their reactions with arenes, see (a) G. A. Olah and A. M. White, J. Am. Chem. Soc., 1967, 89, 4752.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 4752
    • Olah, G.A.1    White, A.M.2
  • 12
    • 0004474274 scopus 로고
    • and the references cited therein
    • (e) T. Ohwada and K. Shudo, J. Org. Chem., 1989, 54, 5227, and the references cited therein.
    • (1989) J. Org. Chem. , vol.54 , pp. 5227
    • Ohwada, T.1    Shudo, K.2
  • 17
    • 0347627109 scopus 로고    scopus 로고
    • Eur. Patent 1990, 356230
    • Dications (19-27) were preferred based on the participation of the non-bonded electron pairs of both heteroatoms in charge delocalization (with the exception of 24). Favorable formation of dications (20, 21, 26 and 27) also conforms to positional selectivity of electrophilic substitution reactions of 11 and 13 in strong acids (hydrogen-deuterium exchange, nitration, etc.) to give 6- and 8-substituted 2- and 4-quinolones, see, for example: (a) R. M. Welch, A. R. Brown, and A. P. Phillips, Eur. Patent 1990, 356230.
    • Welch, R.M.1    Brown, A.R.2    Phillips, A.P.3
  • 18
    • 19644384929 scopus 로고
    • (b) A. R. Katritzky, B. Terem, E. V. Scriven, S. Clementi, and H. O. Tarhan, J. Chem. Soc., Perkin Trans. II, 1975, 1600. The possibility of additional N-protonation of 11a-13a to give the Corresponding N,N-diprotonated dications was not considered to be kinetically favorable. See, for example, the discussion on that subject for 1- and 2-isoquinolinols: Ref. 2b.
    • (1975) J. Chem. Soc., Perkin Trans. II , pp. 1600
    • Katritzky, A.R.1    Terem, B.2    Scriven, E.V.3    Clementi, S.4    Tarhan, H.O.5
  • 21
    • 0000189651 scopus 로고
    • Becke's three parameter hybrid method using the LYP correlation functional: (a) A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648
    • Becke, A.D.1
  • 27
    • 0346366413 scopus 로고    scopus 로고
    • note
    • 2 and q•, see, for example, Ref. 2a and 2b.
  • 28
    • 0000795644 scopus 로고
    • Under the reaction conditions cyclohexane exists in an equilibrium with methylcyclopentane, see: C. D. Nenitzescu and R. Cantuniari, Chem. Ber., 1933, 66, 1097.
    • (1933) Chem. Ber. , vol.66 , pp. 1097
    • Nenitzescu, C.D.1    Cantuniari, R.2
  • 29
    • 0347627110 scopus 로고    scopus 로고
    • note
    • 3. See Ref. 2b.
  • 30
    • 0346996304 scopus 로고    scopus 로고
    • note
    • 3 at 25 °C gave in 10% conversion a complex reaction mixture.
  • 31
    • 0345735265 scopus 로고
    • and the references cited therein
    • K. M. Johnston, Tetrahedron, 1968, 24, 5595, and the references cited therein.
    • (1968) Tetrahedron , vol.24 , pp. 5595
    • Johnston, K.M.1
  • 33
    • 0345735266 scopus 로고    scopus 로고
    • note
    • The reaction mixture did not contain compound (11). A single byproduct (∼15%) of the reaction corresponds to the condensation of 35 with phenyl group of product (32).
  • 36
    • 0345735264 scopus 로고    scopus 로고
    • German Patent, Hoechst AG, DE 2426851, 1976
    • G. Salbeck, German Patent, Hoechst AG, DE 2426851, 1976.
    • Salbeck, G.1
  • 37
    • 0345735260 scopus 로고    scopus 로고
    • note
    • As a mixture of 31/28 (95:5).
  • 39
    • 0346366412 scopus 로고    scopus 로고
    • note
    • The data are taken from the spectra of mixture of the cis and trans isomers.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.