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Chemistry of Heterocyclic Compounds

, Volume 35, Issue 1, pp 64–67 | Cite as

Synthesis of 11-bromo-9-methyl-6-methylene-3-methylthio-5,6,9,10-tetrahydro-8H-[1,2,4]triazolo[3′,4′;3,4]pyrazino[1,2-c]pyrimidine-8,10-dione from 4-allyl-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-6-pyrimidinylcarbonyl)thiosemicarbazide

  • G. Myakushkene
  • P. Vainilavichyus
Article

Abstract

4-Allyl-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-6-pyrimidinylcarbonyl)thiosemicarbazide is cyclized in alkaline medium into 4-allyl-3-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-6-pyrimidinyl)-1,2,4-triazoline-3-thione, which is converted on alkylation with iodomethane into the methylthio derivative. Reaction of the latter with bromine occurs with formation of 3-(5-bromo-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-6-pyrimidinyl)-4-(2,3-dibromopropyl)-5-methylthio-1,2,4-triazole, dehydrobromination of which with potassium carbonate leads to formation of the first representative of a new heterocyclic system, viz. 11-bromo-9-methyl-6-methylene-3-methylthio-5,6,9,10-tetrahydro-8H-[1,2,4]triazolo[3′,4′:3,4]pyrazino[1,2-c]pyrimidine-8,10-dione.

Keywords

Potassium Organic Chemistry Alkylation Dione Triazole 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Kluwer Academic/Plenum 1999

Authors and Affiliations

  • G. Myakushkene
  • P. Vainilavichyus

There are no affiliations available

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