Novel ring transformations of condensed [1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thiones effected by dialkyl-acetylenedicarboxylates

Mónika Simó, A. Csámpai, V. Harmat, Orsolya Barabás, Gábor Magyarfalvy

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

On heating with dialkyl-acetylenedicarboxylates in DMF condensed [1,2,4]-triazolo[4,3-b] pyridazine-6(5H)-one-3(2H)-thiones undergo unprecedented ring transformations yielding novel tetracyclic 1,3-diazepines and thiazolotriazole derivatives depending on the applied reaction temperature. The observed substrate selectivity was interpreted on the basis of the results of comparative theoretical calculations carried out at semiempirical level (AM1).

Original languageEnglish
Pages (from-to)7191-7198
Number of pages8
JournalTetrahedron
Volume57
Issue number33
DOIs
Publication statusPublished - Aug 13 2001

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Thiones
Heating
Derivatives
Temperature
Substrates
pyridazine
1-deoxy-1-morpholinofructose

Keywords

  • Ring transformation
  • Semiempirical calculations
  • Structure determination
  • Substrate selectivity

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel ring transformations of condensed [1,2,4]triazolo[4,3-b]pyridazine-6(5H)-one-3(2H)-thiones effected by dialkyl-acetylenedicarboxylates. / Simó, Mónika; Csámpai, A.; Harmat, V.; Barabás, Orsolya; Magyarfalvy, Gábor.

In: Tetrahedron, Vol. 57, No. 33, 13.08.2001, p. 7191-7198.

Research output: Contribution to journalArticle

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AU - Magyarfalvy, Gábor

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