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Volumn 63, Issue 22, 1998, Pages 7840-7850

Synthesis of substituted pyridines via regiocontrolled [4 + 2] cycloadditions of oximinosulfonates

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EID: 0000589131     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981014e     Document Type: Article
Times cited : (74)

References (81)
  • 12
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    • For reviews of the chemistry of Meldrum's acid and its derivatives see: (a) McNab, H. Chem. Soc. Rev. 1978, 7, 345.
    • (1978) Chem. Soc. Rev. , vol.7 , pp. 345
    • McNab, H.1
  • 17
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    • Boulton, A. J.; McKillop, A., Eds.; Pergamon: Oxford
    • Jones, G. In Comprehensive Heterocydic Chemistry; Boulton, A. J.; McKillop, A., Eds.; Pergamon: Oxford, 1984; Vol. 2, Part 2A, pp 395510.
    • (1984) Comprehensive Heterocydic Chemistry , vol.2 , Issue.PART 2A
    • Jones, G.1
  • 24
    • 33744847126 scopus 로고    scopus 로고
    • Sauvage, J.P., Hosseini; M. W., Eds.; Pergamon: New York
    • Baxter, P. N. W. In Comprehensive Supramolecular Chemistry; Sauvage, J.P., Hosseini; M. W., Eds.; Pergamon: New York, 1996; Vol. 9, pp 165212.
    • (1996) Comprehensive Supramolecular Chemistry , vol.9 , pp. 165212
    • Baxter, P.N.W.1
  • 37
    • 0343193917 scopus 로고
    • (14)Meldrum's acid is itself sufficiently acidic to catalyze the nitrosation reaction. For the first report of the nitrosation of Meldrum's acid, see: Eistert, B.; Geiss, F. Chem. Ber. 1961, 94, 929.
    • (1961) Chem. Ber. , vol.94 , pp. 929
    • Eistert, B.1    Geiss, F.2
  • 38
    • 85034168481 scopus 로고    scopus 로고
    • Neutralization before the addition of TsCl helps prevent the acid-promoted addition of methanol to 8 (the product is obtained in 35% yield if buffer is not used)
    • Neutralization before the addition of TsCl helps prevent the acid-promoted addition of methanol to 8 (the product is obtained in 35% yield if buffer is not used).
  • 41
    • 0029921206 scopus 로고    scopus 로고
    • NCS in conjunction with NaOMe has recently been used for the oxidation of tetrahydropyridines to pyridines: De Kimpe, N.; Keppens, M.; Fonck, G. Chem. Commun. 1996, 635.
    • (1996) Chem. Commun. , pp. 635
    • De Kimpe, N.1    Keppens, M.2    Fonck, G.3
  • 42
    • 85034186766 scopus 로고    scopus 로고
    • note
    • Care must be exercised to avoid strongly basic workup conditions since the pyridine esters are sensitive to hydrolysis. This difficulty was circumvented by performing a neutral workup with pH 7 phosphate buffer.
  • 56
    • 85034184306 scopus 로고    scopus 로고
    • note
    • Fusaric acid is a nanomolar inhibitor of dopamine /J-hydroxylase (IC50 = 3.0 x 10-" M), see: ref 24d.
  • 70
    • 85034183588 scopus 로고    scopus 로고
    • The Mosher ester of racemic 34 was also prepared, and the diastereomers were found to be well resolved by both 'H and 19F NMR spectroscopy
    • The Mosher ester of racemic 34 was also prepared, and the diastereomers were found to be well resolved by both 'H and 19F NMR spectroscopy.
  • 71
    • 85034164045 scopus 로고    scopus 로고
    • note
    • The isolation of (S)-(+)-fusarinolic acid was complicated by its high solubility in aqueous solution. Fortunately, (SH+)-fusarinolic acid could be recovered from an appropriately buffered (pH 2.5) aqueous solution by continuous liquid-liquid extraction with dichloromethane for 2 days.
  • 72
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    • and references therein
    • (a) Gassman, P. G. Ace. Chem. Res. 1970, 3, 26 and references therein,
    • (1970) Chem. Res. , vol.3 , pp. 26
    • Ace, G.P.G.1
  • 75
    • 85034197289 scopus 로고    scopus 로고
    • note
    • We briefly conducted experiments with the aim of trapping the putative intermediate 44 with cyanide ion. A variety of cyanide sources and solvents were examined, but only the normal pyrroline product could be isolated. Attack of cyanide at the sulfonyl group of 43 may be responsible for pyrroline formation in these reactions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.