1632-30-0Relevant articles and documents
Study of the Prototropic Tautomerism of 8-Azatheophylline by 13C and 15N NMR Spectroscopy
Gerrit, L'abbe,Persoons, Marie-Anne,Toppet, Suzanne
, p. 362 - 364 (1987)
Comparison of the 13C and 15N NMR spectra of 8-azatheophylline with those of its three methylated derivatives and other model compounds from the literature showed that 8-azatheophylline exists to the extent of 80percent in the N-2 tautomeric form in DMSO solution. KEY WORDS 13C NMR 15N NMR Prototropism 4,6-Dimethyl-5,7-dioxo-1,2,3-triazolopyrimidine
ISOMERIZATION AND DEALKYLATION OF METHYLATED XANTHINIUM DERIVATIVES
Muravich-Aleksandr, Kh. L.,Kolesova, M. B.,Pernikova, V. G.,Smirnova, N. V.
, p. 562 - 567 (2007/10/02)
The isomerization or dealkylation of methylated xanthinium derivatives takes place with the participation of nucleophiles and is facilitated in the presence of a sterically hindered configuration.When heated, 7,9-dimethyl- and 1,7,9-trimethylxanthinium salts isomerize to theobromine and caffeine respectively.Under these conditions 3,7,9-trimethyl- and 1,3,7,9-tetramethylxanthinium salts are dealkylated.The 1,7,9- and 3,7,9-trimethylxanthinium betaines are isomerized quantitatively to caffeine.The role of the nucleophile under these conditions is played by the negatively charged fragment in the pyridine part of molecule.An intermolecular mechanism of rearrangement of the 3,7,9-trimethylxanthinium betaine is demonstrated.The sterically overloaded 1,3,8,9-tetramethylxanthine and 1,3,9-trimethyl-8-azaxanthine and not the charged compounds undergo rearrangement.In these cases the nucleophilic center is the doubly bonded N7 atom in the five-membered ring.