Synthetic procedure to pyrido[2,1-f][1,2,4]triazinium salt and related compounds

Sándor Bátori, Dorottya Csányi, Daniella Takács, O. Egyed, Z. Riedl, G. Hajós

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

N-aminopyridyl ketone salts were reacted with formamide to yield heteroaromatic pyrido[2,1-f][1,2,4]triazinium salts. Upon storage of these products in the presence of water, formation of covalent hydrates have been observed. Reaction of the same starting compound with urethane yielded 3-chloropyrido[2,1-f][1,2,4]triazinium salt which readily reacted with secondary amines to afford 3-amino derivatives. An analogous ring closure reaction of 2-formylaminomethyl- and formaminobenzylpyridine allowed the synthesis of the partially reduced 3,4-dihydropyrido[2,1-f][1,2,4]triazinium compounds. The cyclization procedure was also applied for the synthesis of the related pyrimido[2,1-f][1,2,4]triazinium salt.

Original languageEnglish
Pages (from-to)180-185
Number of pages6
JournalTetrahedron
Volume75
Issue number2
DOIs
Publication statusPublished - Jan 11 2019

Keywords

  • Covalent hydrate
  • Fused triazinium salt
  • Heteroaromatic
  • Ring closure
  • Zwitterion

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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