93703-23-2Relevant articles and documents
Purines. XIV [1]. Synthesis and properties of 8-nitroxanthine and its N- methyl derivatives
Mosselhi,Pfleiderer
, p. 1221 - 1228 (2007/10/02)
Xanthine (1) and its N-methyl derivatives 2-16 have been nitrated to the corresponding 8-nitro derivatives 17-32 under different reaction conditions. Nitration in glacial acetic acid with nitric acid works well with the N-7 unsubstituted and some of the 9-methylxanthines, respectively, whereas the 7- methylxanthine derivatives react best with nitronium tetrafluoroborate in sulfolane or glacial acetic acid. The 8-nitro group can be displaced nucleophilically to form 8-chloro-, 33, 34, 8-ethoxy-, 35, 36, and uric acid derivatives 37-40, respectively. The newly synthesized 8-nitroxanthines have been characterized by elemental analyses, pK-determinations and uv and 1H- nmr spectra.
ELECTROPHILIC AND NUCLEOPFILIC SUBSTITUTION REACTION IN THE SERIES OF 3-METHYLXANTHINE AND ITS DERIVATIVES
Priimenko, B.A.,Romanenko, N.I.,Klyuev, N.A.,Fedulova, I.V.,Gnatov, N.I.,Garmash, S.N.
, p. 924 - 927 (2007/10/02)
The reactions of nitration and bromination of 3-methylxanthine were studied.Heating 3-methyl-8-nitroxanthine with con.HCl and HBr leads to a replacement of the nitro group by a halogen atom.The alkylation of 8-haloxanthines by alkyl halides were studied.It was shown that boiling 7-substituted 3-methyl-8-bromoxanthine derivatilves with POCl3 and PCl5 leads to the formation of 2,6,8-trichloro-7-alkylpurines.The structure of synthetized compounds was confirmed by counter synthesis, the data of elementary analysis, and mass spectrometry.
