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Purins, pyrimidines, and related condensed systems. 22. Synthesis and heterocyclization of 7-alkynyl- and 6,7-dialkynyllumazines

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Abstract

The reaction of 6,7-dichloro-1,3-dimethyllumazine with terminal alkynes under Sonogashira conditions gave 7-alkynyl-6-chloro- and 6,7-dialkynyl-1,3-dimethyllumazines. It was found that the alkynyllumazines readily add primary and secondary alkylamines at the 7-alkynyl group to form stable enamines, hydrolysis of which gives 7-(β-hydroxyvinyl)lumazines. The heterocyclization of 7-(β-aminovinyl)- and 7-(β-hydroxyvinyl)lumazines has been carried out to give pyrrolo-, pyrido-, furo-, and pyranopteridines.

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Authors and Affiliations

  1. Rostov State University, Rostov-on-Don, 344090, Russia

    Shi Van Dang, A. V. Gulevskaya, A. F. Pozharskii & R. V. Kotelevskaya

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  1. Shi Van Dang
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  2. A. V. Gulevskaya
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  3. A. F. Pozharskii
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  4. R. V. Kotelevskaya
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 140–152, January, 2005.

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Van Dang, S., Gulevskaya, A.V., Pozharskii, A.F. et al. Purins, pyrimidines, and related condensed systems. 22. Synthesis and heterocyclization of 7-alkynyl- and 6,7-dialkynyllumazines. Chem Heterocycl Compd 41, 124–135 (2005). https://doi.org/10.1007/s10593-005-0118-3

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  • DOI: https://doi.org/10.1007/s10593-005-0118-3

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