- Recent advances in selective syntheses of 6- and 7-substituted pteridines
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Novel regioselective methods for construction of biologically important pteridines which contain carbon substituents on the 6- or 7-position using pteridine ring-forming cyclocondensations, nucleophilic substitution reactions, and radical reactions are reviewed.
- Murata, Shizuaki,Kiguchi, Kenji,Sugimoto, Takashi
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- PURINES, PYRIMIDINES AND CONDENSED SYSTEMS BASED ON THEM. 10. REACTIVITY OF 1,3-DIMETHYL-6-CHLOROLUMAZINE WITH RESPECT TO AMINES: COMPETITION OF AMINODECHLORINATION AND AMINODEHYDROGENATION REACTIONS
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1,3-Dimethyl-6-chlorolumazine reacts with secondary alkylamines and hydrazine to form 1,3-dimethyl-6-amino(hydrazino) derivatives in good yields.At the same time, 6-chloro-7-amino-1,3-dimethyllumazines are formed by the action of primary amines and liquid ammonia, in addition to the nucleophilic substitution products of chlorine.
- Gulevskaya, A. V.,Pozharskii, A. F.,Chernyshev, A. I.,Kuz'menko, V. V.
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- Pteridines, LXXII. - Synthesis and Properties of 6- and 7-Amino-1,3-dimethyllumazines
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The synthesis of 6- and 7-amino-, -methylamino-, and -dimethylamino-1,3-dimethyllumazines (2-4 and 12-14) is described.The nucleophilic displacement reaction proceeds easily with the 7-halo-1,3-dimethyllumazines 10, 11 whereas the amidation of 6-hydroxy-1,3-dimethyllumazine (1) with phenyl diamidophosphates is recommended for the formation of 6-amino derivatives. 6-Amino-1,3-dimethyllumazine (2) is synthesized best from 6-chloro-1,3-dimethyllumazine (7) via the 6-hydrazino derivative 5 and subsequent reduction.From pKa value determinations and UV absorption spectra of the cationic and neutral forms can be seen that protonation takes place in both series at N-5.The physical properties of the newly synthesized compounds are discussed.
- Steppan, Heinz,Hammer, Joachim,Baur, Ralph,Gottlieb, Raphael,Pfleiderer, Wolfgang
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p. 2135 - 2145
(2007/10/02)
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