PURINS, PYRIMIDINES, AND RELATED CONDENSED SYSTEMS. 22. SYNTHESIS AND HETEROCYCLIZATION OF 7-ALKYNYL- AND 6,7-DIALKYNYLLUMAZINES

Authors

  • Ши Ван Данг Rostov State University, Rostov-on-Don 344090
  • А. В. Гулевская Rostov State University, Rostov-on-Don 344090
  • А. Ф. Пожарский Rostov State University, Rostov-on-Don 344090
  • Р. В. Котелевская Rostov State University, Rostov-on-Don 344090

DOI:

https://doi.org/10.1007/8413

Keywords:

1-alkynes, 7-alkynyl-6-chloro-1, 3-dimethyllumazines, 6, 7-dialkynyl-1, 7-dichloro-1, 3-dimethyllumazine, enamines, pyrano[2, 3-g]pteridine-2, 4(1H, 3H)-diones, pyrano-[3, 4-g]pteridine-2, pyrido[3, pyrrolo[2, 3-g]pteridine-6, 8(5H, 7H)-diones, furo[2, Sonogashira cross conjugation, metallocomplex catalysis

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.

How to Cite
Van Dang, S.; Gulevskaya, A. V.; Pozharskii, A. F.; Kotelevskaya, R. V.  Chem. Heterocycl. Compd. 2005, 41, 124. [Khim. Geterotsikl. Soedin. 2005, 140.]

For this article in the English edition, see DOI 10.1007/s10593-005-0118-3


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Published

2023-12-06

Issue

No. 1 (2005)

Section

Original Papers