Journal of the Chemical Society. Perkin transactions I p. 825 - 830 (1985)
Update date:2022-08-04
Topics:
Atkinson, Robert S.
Gawad, Nagwa A.
The N-nitrenes generated by oxidation of N-aminoquinazolones (1) and (2) are trapped by the remote 2,4-dimethoxyphenyl ring.Oxidation of (1) in benzene gives the metacyclophane (3) in 60percent isolated yield whereas oxidation in methanol gives (5), (6) and (8).The structures of the acetal (5) and the imine (8) have been confirmed by X-ray crystallography.Oxidation of (2) in methanol yields (11) and (16).An explanation is offered for the selectivity for attack on the 2,3- or 5,6-double bonds of the dimethoxyphenyl ring by the N-nitrene derived from (1).
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Doi:10.1055/s-1985-31111
(1985)Doi:10.1007/BF00914989
(1961)Doi:10.1016/0022-328X(85)87380-0
(1985)Doi:10.1055/s-1985-31139
(1985)Doi:10.1246/bcsj.56.3694
(1983)Doi:10.3762/bjoc.15.66
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