Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies on Heteroaromaticity. XXI. 1,3-Dipolar Cycloaddition of N-Phenyl-C-(6-uracilyl)nitrone
Tadashi SasakiMoriyasu Ando
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1968 Volume 41 Issue 12 Pages 2960-2963

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Abstract

N-Phenyl-C-(6-uracilyl)nitrone (II) was prepared in 80% yield from orotaldehyde (I) and phenylhydroxylamine. II underwent 1,3-dipolar cycloaddition reactions with several ethylenic and acetylenic compounds to afford the corresponding isoxazolidines (IIIa—f) and isoxazolines (IVg—i). Similar reactions of II with phenyl isocyanate, carbon disulfide and with enamine were carried out successfully. The structural elucidation of these products was done on the basis of their NMR spectra.

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