Structural studies on 9‐hydrazono‐6,7,8,9‐tetrahydro‐4‐oxo‐4H‐pyrido[1,2‐a]pyrimidines by 1H, 13C and 15N NMR spectroscopy

Gábor Tóth, A. Szöllösy, Attila Almásy, Benjámin Podányi, I. Hermecz, Tibor Breining, Zoltán Mészáros

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Abstract

1H, 13C and 15N NMR studies demonstrated that 9‐hydrazono‐6,7,8,9‐tetrahydro‐4‐oxo‐4H‐pyrido‐[1,2‐a] pyrimidlnes exist as an equilibrium mixture of Z‐E isomers in the hydrazono–imino tautomeric form having an exocyclic double bond. Proton‐catalysed Z‐E interconversion is fast. Substituent and solvent effects revealed that the decisive factors controlling the Z:E ratio are internal hydrogen bonding in the Z‐isomer, stabilization by solvation and steric interaction.

Original languageEnglish
Pages (from-to)687-693
Number of pages7
JournalOrganic Magnetic Resonance
Volume21
Issue number11
DOIs
Publication statusPublished - 1983

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ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

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