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Volumn 53, Issue 28, 1997, Pages 9715-9726

A new multicomponent synthesis of 1,2,3,4-tetrahydroquinolines

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; ALDEHYDE; ALKADIENE; ALKENE; ENAMINE; IMINE;

EID: 0030829336     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00594-2     Document Type: Article
Times cited : (48)

References (51)
  • 17
    • 0013541089 scopus 로고
    • Weissberger, A.; Taylor, E. C. Eds.; John Wiley & Sons, London
    • Jones, G. in The Chemistry of Heterocyclic Compounds, Weissberger, A.; Taylor, E. C. Eds.; vol. 32, part 1, pp 93 - 318, John Wiley & Sons, London, 1977. For a review on the synthesis of quinolines derivatives from imines via[4+2] cycloaddition see: Boger, D.L. Tetrahedron 1983, 39, 2869.
    • (1977) The Chemistry of Heterocyclic Compounds , vol.32 , Issue.PART 1 , pp. 93-318
    • Jones, G.1
  • 18
    • 45449097286 scopus 로고
    • Jones, G. in The Chemistry of Heterocyclic Compounds, Weissberger, A.; Taylor, E. C. Eds.; vol. 32, part 1, pp 93 - 318, John Wiley & Sons, London, 1977. For a review on the synthesis of quinolines derivatives from imines via[4+2] cycloaddition see: Boger, D.L. Tetrahedron 1983, 39, 2869.
    • (1983) Tetrahedron , vol.39 , pp. 2869
    • Boger, D.L.1
  • 30
    • 0342520470 scopus 로고    scopus 로고
    • note
    • 3. However, they behave identically.
  • 31
    • 0343825741 scopus 로고    scopus 로고
    • note
    • 2).
  • 32
    • 0343390128 scopus 로고    scopus 로고
    • note
    • Since the two isomers of 28 and 29 can be converted into 30 and 31, respectively, at different rates, the isomer ratios reported in Table 4 may not reflect the original composition of the diastereoisomeric mixture.
  • 33
    • 0342954700 scopus 로고    scopus 로고
    • note
    • From these reactions complex mixtures of products were obtained. Apparently, these aldehydes react with two molecules of imine 1.
  • 34
    • 0343390129 scopus 로고    scopus 로고
    • note
    • Unreacted imine 1 was recovered in high yield from these reactions.
  • 35
    • 0343825740 scopus 로고    scopus 로고
    • note
    • From the reaction with methyl acetacetate in nitromethane a product was obtained in 26% yield as a mixture of isomers, likely deriving from reaction of C-2 and C-4 of methyl acetacetate with two molecules of 1.
  • 36
    • 0342954679 scopus 로고    scopus 로고
    • note
    • (R)-O,O-Cyclohexylidene glyceraldehyde behaved similarly to 34 affording products analogous to 35 and 36, in 23 and 39% yield, respectively. Both were mixtures of diastereoisomers; the former was optically inactive and the latter optically active.
  • 37
    • 0343390096 scopus 로고    scopus 로고
    • note
    • This exchange reaction is currently under active investigation in our laboratories.
  • 38
    • 0343825715 scopus 로고    scopus 로고
    • note
    • 3 hydrolysis promoted either by the water molecules associated with the catalyst (see ref. 11), or by traces of water present in the solvents.
  • 39
    • 0343825716 scopus 로고    scopus 로고
    • note
    • 3 co-ordinates the nitrogen of imine 1 (see ref. 10).
  • 41
    • 0343825714 scopus 로고    scopus 로고
    • note
    • This product was a 86 : 14 mixture of trans and cis isomers both featuring an equatorial C-2 Ph substituent.
  • 42
    • 0342459402 scopus 로고    scopus 로고
    • note
    • 3, and to trap adduct C with dienophiles. In addition, replacement of 2-methylpropanal 2 with its N-morpholinoenamine did not afford any THQ.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.