Journal of Organic Chemistry p. 1378 - 1383 (1981)
Update date:2022-08-03
Topics:
Iwasa, Kinuko
Chinnasamy, P.
Shamma, Maurice
Reduction-oxidation of trans- or cis-canadine N-oxide (3 or 12) in aerated sodium in liquid ammonia yields nitrone 4 and a little of amine 5.Photolysis of 4 in methanol gives rise to amide 8, lactam 9, and methyl ether 10.Attempted reduction-oxidation of either trans- or cis-xylopinine N-oxides (14 or 15) furnishes only amine 16.The two N-oxides of nandinine (20) proved to be only sparingly soluble in the reaction medium and thus provided only limited yields of nitrone 23.The yield of nitrone is also curtailed if a methyl group is present at C-13 of the starting berbine N-oxide.
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