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Volumn , Issue 23, 2003, Pages 4601-4610

2-Substituted (Azulen-1-yl)ethenes

Author keywords

C C coupling; Nitrogen heterocycles; Schiff bases; Solvent free synthesis

Indexed keywords

1,3 DIKETONE; ARYLACETIC ACID DERIVATIVE; AZULENE DERIVATIVE; ETHYLENE DERIVATIVE; KETONE; MALONIC ACID; MALONIC ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SCHIFF BASE; UNCLASSIFIED DRUG;

EID: 0344306308     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300346     Document Type: Article
Times cited : (27)

References (42)
  • 13
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    • (Houben-Weyl), B. V/2c, Georg Thieme Verlag, Stuttgart, New York
    • A short review of the syntheses of different vinylazulenes was presented by: K.-P. Zeller, in Methoden der Organischen Chemie (Houben-Weyl), B. V/2c, Georg Thieme Verlag, Stuttgart, New York, 1985.
    • (1985) Methoden der Organischen Chemie
    • Zeller, K.-P.1
  • 20
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    • note
    • For the synthesis of 1-(azulen-1-yl)-2-phenylethene [9(H)] we applied a Wittig procedure in the presence of n-butyllithium This resulted in, together with unchanged 1-azulenecarbaldehyde (20 %), a mixture of (Z)- and (E)-9(H) (in yields of 44.5 % and 7.5 %, respectively).
  • 21
    • 0000872237 scopus 로고
    • A. E. Siegrist, Helv. Chim. Acta 1967, 50, 907-957; A. E. Siegrist, H. R. Meyer, Helv. Chim. Acta 1969, 52, 1282-1323; A. E. Siegrist, P. Liechti, H. R. Meyer, K. Weber, Helv. Chim. Acta 1969, 52, 2521-2553; A. E. Siegrist, Helv. Chim. Acta 1981, 64, 662-685.
    • (1967) Helv. Chim. Acta , vol.50 , pp. 907-957
    • Siegrist, A.E.1
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    • A. E. Siegrist, Helv. Chim. Acta 1967, 50, 907-957; A. E. Siegrist, H. R. Meyer, Helv. Chim. Acta 1969, 52, 1282-1323; A. E. Siegrist, P. Liechti, H. R. Meyer, K. Weber, Helv. Chim. Acta 1969, 52, 2521-2553; A. E. Siegrist, Helv. Chim. Acta 1981, 64, 662-685.
    • (1969) Helv. Chim. Acta , vol.52 , pp. 1282-1323
    • Siegrist, A.E.1    Meyer, H.R.2
  • 23
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    • A. E. Siegrist, Helv. Chim. Acta 1967, 50, 907-957; A. E. Siegrist, H. R. Meyer, Helv. Chim. Acta 1969, 52, 1282-1323; A. E. Siegrist, P. Liechti, H. R. Meyer, K. Weber, Helv. Chim. Acta 1969, 52, 2521-2553; A. E. Siegrist, Helv. Chim. Acta 1981, 64, 662-685.
    • (1969) Helv. Chim. Acta , vol.52 , pp. 2521-2553
    • Siegrist, A.E.1    Liechti, P.2    Meyer, H.R.3    Weber, K.4
  • 24
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    • A. E. Siegrist, Helv. Chim. Acta 1967, 50, 907-957; A. E. Siegrist, H. R. Meyer, Helv. Chim. Acta 1969, 52, 1282-1323; A. E. Siegrist, P. Liechti, H. R. Meyer, K. Weber, Helv. Chim. Acta 1969, 52, 2521-2553; A. E. Siegrist, Helv. Chim. Acta 1981, 64, 662-685.
    • (1981) Helv. Chim. Acta , vol.64 , pp. 662-685
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    • (Ed.: S. Patay), Interscience Publisher Wiley & Sons, London, New York, Sidney, and following
    • K. Harada, in The Chemistry of C = N bond (Ed.: S. Patay), Interscience Publisher Wiley & Sons, London, New York, Sidney, 1970, p. 262 and following.
    • (1970) The Chemistry of C = N Bond , pp. 262
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    • note
    • 3) obtained from para-anisidine, an amine that is more stable and less harmful.
  • 30
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    • note
    • An alternative synthesis of the compound 18 was performed by the authors by use of a Wittig reaction between ortho-phenylenediylide and two equivalents of azulenecarbaldehyde. A complex mixture of trans-trans, cis-cis and cis-trans isomers of 18, together with internal cyclization compounds, was obtained. The results will be published.
  • 33
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    • V. M. Rodionov, E. V. Yavorskaya, Zh. Obschei. Khim. 1953, 23, 983-986; Zh. Obschei. Khim. 1955, 25, 2147-2150.
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  • 37
    • 85041878587 scopus 로고    scopus 로고
    • note
    • 5),[9d] and 37[7a] - only 13 was completely characterized.
  • 38
    • 85041880965 scopus 로고    scopus 로고
    • note
    • The UV/Vis spectra will be reported and commented on in another paper in preparation.
  • 39
    • 85041869530 scopus 로고    scopus 로고
    • note
    • 2); other spectra are reported in the electronic Supporting Information; for details see also the footnote on the first page of this article.
  • 40
    • 85041867509 scopus 로고    scopus 로고
    • note
    • The diethene 18 and the compound 19 have the same molecular ion signal in their mass spectra.
  • 41
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    • note
    • Compound 8 was a gift from Prof. Klaus Hafner.
  • 42
    • 85041882801 scopus 로고    scopus 로고
    • note
    • 3) remained unchanged and the compound 34 was produced in about 20 % yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.