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Volumn 55, Issue 6, 1999, Pages 1519-1559

3-acetoxyaminoquinazolinones (QNHOAc) as aziridinating agents: Ring- opening of N-(Q)-substituted aziridines

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIRIDINE DERIVATIVE; HETEROCYCLIC AMINE; IMINE; PERACETIC ACID; QUINAZOLINONE DERIVATIVE;

EID: 0033524716     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01199-5     Document Type: Review
Times cited : (199)

References (115)
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    • Padwa, A.1    Woolhouse, A.D.2
  • 16
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    • Davis, F.A.1    Sheppard, A.C.2
  • 17
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    • Davis, F. A.; Sheppard, A. C. Tetrahedron, 1989, 45, 5703, see however, Andreae, S.; Schmitz, E. Synthesis, 1991, 327.
    • (1991) Synthesis , pp. 327
    • Andreae, S.1    Schmitz, E.2
  • 19
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    • Ed. Lwowski, W., Interscience, New York
    • (b) Lwowski, W. in Nitrenes, Ed. Lwowski, W., Interscience, New York, 1970, pp.185-224;
    • (1970) Nitrenes , pp. 185-224
    • Lwowski, W.1
  • 66
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    • Ref. 5
    • Ref. 5, p.154.
  • 72
    • 0000627007 scopus 로고
    • Bartlett, P.D. Rec. Chem. Prog., 1957, 18, 111; see also, Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc., 1997, 119, 3385; Berti, G. in Topics in Stereochemistry, Eds. Allinger, N. L.; Eliel, E. L., Wiley-Interscience, New York, 1973, vol. 7.
    • (1957) Rec. Chem. Prog. , vol.18 , pp. 111
    • Bartlett, P.D.1
  • 73
    • 0030909214 scopus 로고    scopus 로고
    • Bartlett, P.D. Rec. Chem. Prog., 1957, 18, 111; see also, Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc., 1997, 119, 3385; Berti, G. in Topics in Stereochemistry, Eds. Allinger, N. L.; Eliel, E. L., Wiley-Interscience, New York, 1973, vol. 7.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 3385
    • Singleton, D.A.1    Merrigan, S.R.2    Liu, J.3    Houk, K.N.4
  • 74
    • 0013474532 scopus 로고
    • Eds. Allinger, N. L.; Eliel, E. L., Wiley-Interscience, New York
    • Bartlett, P.D. Rec. Chem. Prog., 1957, 18, 111; see also, Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc., 1997, 119, 3385; Berti, G. in Topics in Stereochemistry, Eds. Allinger, N. L.; Eliel, E. L., Wiley-Interscience, New York, 1973, vol. 7.
    • (1973) Topics in Stereochemistry , vol.7
    • Berti, G.1
  • 75
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  • 82
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    • Dissertation, University of Zürich
    • Dr. Lienhard Hoesch (University of Zürich) showed that reaction of with LTA at low temperature (-50 deg;C) produced an intermediate that aziridinated subsequently added tetracyclone. Hoesch, L. Dissertation, University of Zürich, 1974.
    • (1974)
    • Hoesch, L.1
  • 86
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    • note
    • Whereas the product from 46 is a mixture of diastereoisomeric aziridines, that from 45 is the result of an (acid-catalysed) transformation of the (single) aziridine diastereoisomer formed.
  • 87
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    • note
    • At the time, the intermediates in oxidative addition of 3-aminoquinazolinones to alkenes were thought to be N-nitrenes.
  • 97
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    • Thesis, Leicester University
    • Tughan, G., Thesis, Leicester University, 1987.
    • (1987)
    • Tughan, G.1


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