The synthesis of a number of 8-(dialkylamino)-and 8-CPBA did not undergo the rearrangement but only yielded the expected N-oxide derivatives 16. This result seems to alkoxyxanthines (3 and 6, respectively) is described. Treatment of 3 with m-chloroperoxybenzoic acid (m-CPBA)
indicate that a necessary structure element for this rearrangement to occur is an atom with an unshared pair of gave by a novel rearrangement 3-(disubstituted amino)-4,7,9-trimethyl-1-oxo-2,4,7,9-tetraazaspiro[4,5]dec-2-ene-electrons to be attached to the 8-position of the investigated xanthines. In agreement with this statement is the fact that 6,8,10-triones 10. Also, the corresponding 3-alkoxysubtituted spiro compounds 12 were obtained by an analogus N-oxides of 8-[(dialkylamino)methyl]caffeines 16 do not undergo the novel rearrangement but rather give the treatment of 8-alkoxyxanthines 6. In attempts to elucidate a tentative mechanism for this rearrangement 8-expected Meisenheimer rearrangement or the Cope elimination depending upon reaction conditions. [(dialkylamino)methyl]caffeines 7 when treated with m- [a]