Reduction of Heterocycles Containing One Nitrogen Atom

REDUCTION OF HETEROCYCLES CONTAINING ONE NITROGEN ATOM AND ONE OXYGEN ATOM... 

Seven-membered heterocycles containing one nitrogen atom may be obtained either from 105 (see p. 376) or 6-amino-6-deoxy-D-glucose (227) by reduction122 to 228, or from 6-azido-6-deoxy-D-glucopyranose (229) by oxidation to 230 followed by reduction of 230 to 231. A... 

VI. Reductions of Other Heterocycles Containing One Nitrogen Atom... 

When the heterocyclic ring contains more than one nitrogen atom, the initial reduction of the A-oxide may take place in the nucleus, or the reduction of the nucleus and the A-oxide function occurs simultaneously. The reduction of quinazoline-3-oxide,166 3-methoxy-2,5-... 

Compounds containing the C=N functional group derivatives undergo anodic oxidation when the nitrogen atom bears an electron-rich heteroatom. Perhaps the simplest such species are aldoximes, which are anodically oxidized to nitrile oxides (34)38. The reaction was carried out in an undivided cell3 , hence the species 34 underwent immediate reduction to a nitrile (equation 19). However, since nitrile oxides are 1,3-dipolar species, one could in principle carry out the oxidation in a divided cell in the presence of a good 1,3-dipolarophile40 to effect the synthesis of substituted heterocycles. 

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