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Volumn 70, Issue 5, 1997, Pages 965-975

Transformation of oximes of phenethyl ketone derivatives to quinolines and azaspirotrienones catalyzed by tetrabutylammonium perrhenate and trifluoromethanesulfonic acid

Author keywords

[No Author keywords available]

Indexed keywords

ACID TREATMENTS; CHLORANIL; DICHLOROETHANE; KETONE DERIVATIVE; REFLUXING; TETRABUTYLAMMONIUM; TRIFLUOROMETHANE SULFONIC ACID;

EID: 0030940775     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.70.965     Document Type: Article
Times cited : (50)

References (34)
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    • Tetrahedron, 48, 2059 (1992).
    • (1992) Tetrahedron. , vol.48 , pp. 2059
  • 5
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    • Pyridines and their benzo derivatives: (V) synthesis
    • ed by A. R. Katritzky, Pergamon Press, Oxford
    • G. Jones, "Pyridines and their Benzo Derivatives: (V) Synthesis", in "Comprehensive Heterocyclic Chemistry", ed by A. R. Katritzky, Pergamon Press, Oxford (1984), Vol. 2, p. 395;
    • (1984) Comprehensive Heterocyclic Chemistry , vol.2 , pp. 395
    • Jones, G.1
  • 11
    • 79951477266 scopus 로고    scopus 로고
    • 42, 121 1959
    • 42, 121 (1959).
  • 15
    • 79951484289 scopus 로고    scopus 로고
    • In the absence of Molecular Sieves 5A, 4-3, 4-methylenedioxyphenyl butan-2-one was obtained in 40% yield by hydrolysis of the oxime 4a along with the quinoline 5a in 45% yield
    • In the absence of Molecular Sieves 5A, 4-(3, 4-methylenedioxyphenyl) butan-2-one was obtained in 40% yield by hydrolysis of the oxime 4a along with the quinoline 5a in 45% yield.
  • 16
    • 79951477682 scopus 로고    scopus 로고
    • The reaction was also examined in the presence of other oxidizing agents, such as manganese dioxide and t-butylhydroperoxide, but the yield of 5a was not satisfactory
    • The reaction was also examined in the presence of other oxidizing agents, such as manganese dioxide and t-butylhydroperoxide, but the yield of 5a was not satisfactory.
  • 19
    • 79951476289 scopus 로고    scopus 로고
    • In most reactions, mixtures of E and Z oximes were employed as starting materials. The ratio of E and Z did not influence the yield of quinolines
    • In most reactions, mixtures of E and Z oximes were employed as starting materials. The ratio of E and Z did not influence the yield of quinolines.
  • 20
    • 33847089444 scopus 로고
    • For the preparation of quinolines, see: C. M. Leir
    • For the preparation of quinolines, see: C. M. Leir, J. Org. Chem., 42, 911 (1977);
    • (1977) J. Org. Chem. , vol.42 , pp. 911
  • 22
    • 79951485524 scopus 로고    scopus 로고
    • In most cases, the Beckmann rearrangement did not proceed at all, but small amounts of ketones were produced by hydrolysis of oximes
    • In most cases, the Beckmann rearrangement did not proceed at all, but small amounts of ketones were produced by hydrolysis of oximes.
  • 23
    • 0000127396 scopus 로고
    • Dienone-phenol rearrangement and related reactions
    • ed by B. M. Trost, Pergamon Press, Oxford
    • D. A. Whiting, "Dienone-Phenol Rearrangement and Related Reactions", in "Comprehensive Organic Synthesis", ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 3, p. 803.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 803
    • Whiting, D.A.1
  • 24
    • 79951493167 scopus 로고
    • in "Studies in Natural Chemistry", ed by A.-ur-Rahman, Elsevier, Amsterdam, Stereoselective Synthesis Part A
    • M. Hanaoka, "Synthesis of Some Isoquinoline Alkaloids via 8, 14-Cycloberbines", in "Studies in Natural Chemistry", ed by A.-ur-Rahman, Elsevier, Amsterdam (1988), Vol. 1, Stereoselective Synthesis (Part A), p. 187.
    • (1988) Synthesis of Some Isoquinoline Alkaloids Via 8, 14-cycloberbines , vol.1 , pp. 187
    • Hanaoka, M.1
  • 27
    • 79951478745 scopus 로고    scopus 로고
    • The reaction in 1, 2-dichloroethane gave a complex mixture
    • The reaction in 1, 2-dichloroethane gave a complex mixture.
  • 28
    • 0028284793 scopus 로고
    • It has been reported that boron trifluoride etherate promotes the dienone-phenol rearrangement of a phenyl group substituted diazaspirodienone under toluene reflux reaction conditions:, and
    • It has been reported that boron trifluoride etherate promotes the dienone-phenol rearrangement of a phenyl group substituted diazaspirodienone under toluene reflux reaction conditions: M. Kobayashi, K. Uneyama, N. Hamada, and S. Kashino, Tetrahedron Lett., 35, 5235 (1994).
    • (1994) Tetrahedron. Lett. , vol.35 , pp. 5235
    • Kobayashi, M.1    Uneyama, K.2    Hamada, N.3    Kashino, S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.