Purines, pyrimidines, and related fused systems. 20. Heterocyclizations of 6-alkynyl-1,3-dimethyllumazines. Synthesis of pyrrole and thiophene analogs of some natural pteridines |
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Authors: | A V Gulevskaya Dang Van Shee A F Pozharskii |
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Institution: | (1) A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088 Kazan, Russian Federation |
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Abstract: | Sonogashira cross-coupling of 6-chloro-1,3-dimethyllumazine with terminal alkynes gave 6-alkynyl derivatives in good yields. Oxidative amination of the latter with primary alkylamines was accompanied by the pyrrole-ring closure to form 1-R"-2-R-6,8-dimethylpyrrolo3,2-g]pteridine-5,7(6H,8H)-diones. The addition of bromine to 6-alkynyllumazines afforded the corresponding dibromoalkenes whose treatment with sodium trithiocarbonate gave rise to 2-R-6,8-dimethylthieno3,2-g]pteridine-5,7(6H,8H)-diones. The latter compounds are close analogs of the metabolite of molybdenum cofactor (molybdopterine). |
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Keywords: | 6-chloro-1 3-dimethyllumazine alkynes metal complex catalysis Sonogashira reaction 6-(alkyn-1-yl)-1 3-dimethyllumazines oxidative amination pyrrolo[3 2-g]pteridine-5 7(6H 8H)-diones thieno[3 2-g]pteridine-5 7(6H 8H)-diones |
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