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Volumn 65, Issue 12, 2000, Pages 3579-3586

General base and general acid catalyzed intramolecular aminolysis of esters. Cyclization of esters of 2-aminomethylbenzoic acid to phthalimidine

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; PHTHALIMIDE DERIVATIVE;

EID: 0034674693     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9906835     Document Type: Article
Times cited : (45)

References (57)
  • 2
    • 77956941740 scopus 로고
    • Boyer, P. D., Ed.; Academic Press: New York, Chapter 4
    • Bruice, T. C. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1970; Chapter 4, Vol. 2, p 217.
    • (1970) The Enzymes , vol.2 , pp. 217
    • Bruice, T.C.1
  • 3
    • 0342631316 scopus 로고
    • Van Tamelen, E. E., Ed.; Academic Press: New York, Chapter 5
    • Fife, T. H. In Bioorganic Chemistry; Van Tamelen, E. E., Ed.; Academic Press: New York, 1977; Chapter 5, p 93.
    • (1977) Bioorganic Chemistry , pp. 93
    • Fife, T.H.1
  • 13
    • 0343501515 scopus 로고    scopus 로고
    • note
    • In comparison, appropriate intramolecular general base catalyzed hydrolysis reactions will be discussed in a following paper.
  • 35
    • 0343937354 scopus 로고    scopus 로고
    • note
    • a of the amine group would reasonably be greater than 25. A low concentration of a reactive species does not, of course, rule out a unimolecular reaction via that species if the rate constant is very large.
  • 36
    • 0343937353 scopus 로고    scopus 로고
    • Unpublished data
    • 0 vs pH is linear with a slope of 1.0 from pH 11.3 to 8.5 (8 points).
    • Bembi, R.1    Fife, T.H.2
  • 39
    • 0342631304 scopus 로고    scopus 로고
    • note
    • a of the leaving group.
  • 41
    • 0343065598 scopus 로고    scopus 로고
    • note
    • a to attack of the neutral amine at the carbonyl is highly improbable. The linear Bronsted plot of Figure 4 indicates that no change in rate-determining step occurs in the general base catalyzed cyclization of I.
  • 42
    • 0343937350 scopus 로고    scopus 로고
    • note
    • Values of β of 0 or 1.0 imply rate-determining proton transfer in the general base catalyzed reaction, whereas β values between 0 and 1.0 imply that bond making or breaking processes are occurring in concert with proton transfer.
  • 43
    • 0343065596 scopus 로고    scopus 로고
    • note
    • B[B].
  • 44
    • 0000217963 scopus 로고
    • Fife, T. H.; Brod, L. H. J. Am. Chem. Soc. 1970, 92, 1681. Capon, B.; Nimmo, K. J. Chem. Soc., Perkin Trans. 2 1975, 1113.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 1681
    • Fife, T.H.1    Brod, L.H.2
  • 48
    • 0343501506 scopus 로고    scopus 로고
    • note
    • A detailed discussion of the mechanistic differences in the intramolecular nucleophilic reactions of methyl 2-aminophenylacetate and methyl 2-aminophenylpropionate was presented in ref 20. See also references cited therein.
  • 52
    • 0000549918 scopus 로고
    • Fife, T. H.; Jao, L. K. J. Am. Chem. Soc. 1968, 90, 4081. Fife, T. H. Acc. Chem. Res. 1972, 5, 264.
    • (1972) Acc. Chem. Res. , vol.5 , pp. 264
    • Fife, T.H.1
  • 57
    • 0343065592 scopus 로고    scopus 로고
    • note
    • Intramolecular nucleophilic attack does not occur via a 4-membered ring transition state in the corresponding 2-aminobenzoate esters. Fife, T.; Bembi, R. Unpublished data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.