ISSN:
1434-193X
Keywords:
1,3,7-Trialkyl-8-(dialkylamino)xanthines
;
1,3,7-Trialkyl-8-(2′,2′,2′-trifluoroethoxy)xanthines
;
8-(Dialkylaminomethyl)caffeines
;
1-Oxo-2,4,7,9-tetraazaspiro[4,5]dec-2-ene-6,8,10-triones
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of a number of 8-(dialkylamino)- and 8-alkoxyxanthines (3 and 6, respectively) is described. Treatment of 3 with m-chloroperoxybenzoic acid (m-CPBA) gave by a novel rearrangement 3-(disubstituted amino)-4,7,9-trimethyl-1-oxo-2,4,7,9-tetraazaspiro[4,5]dec-2-ene-6,8,10-triones 10. Also, the corresponding 3-alkoxy-subtituted spiro compounds 12 were obtained by an analogus treatment of 8-alkoxyxanthines 6. In attempts to elucidate a tentative mechanism for this rearrangement 8-[(dialkylamino)methyl]caffeines 7 when treated with m-CPBA did not undergo the rearrangement but only yielded the expected N-oxide derivatives 16. This result seems to indicate that a necessary structure element for this rearrangement to occur is an atom with an unshared pair of electrons to be attached to the 8-position of the investigated xanthines. In agreement with this statement is the fact that N-oxides of 8-[(dialkylamino)methyl]caffeines 16 do not undergo the novel rearrangement but rather give the expected Meisenheimer rearrangement or the Cope elimination depending upon reaction conditions.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
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