Ring‐Chain Tautomerism of 3,5‐Disubstituted 5,6,7,8‐Tetrahydro‐3H‐3H‐[1,2,4]oxadiazolo[4,3‐c]pyrimidine, a Novel Heterocyclic Ring System

DezsÓ Korbonits, Erzsébet TóbiaAs‐Héja, KÁLmÁN Simon, PÁL Kolonits

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13 Citations (Scopus)

Abstract

The reaction of 3‐aminopropionamide oxime (7) with two equiv. of benzaldehyde or of a substituted benzaldehyde gives cis‐3,5‐diaryl‐5,6,7,8‐tetrahydro‐3H[1,2,4]oxadiazolo[4,3‐c]‐pyrimidines (cis‐11a‐c,e). According to 1H‐, 13C‐, and 15N‐NMR studies these compounds form in solution a novel triple tautomeric equilibrium comprising cis‐ and trans‐11a‐c, e and 3‐[2‐(benzylidineamino)ethyl]‐5‐aryl‐4,5‐dihydro‐1,2,4‐oxaliazoles (10a‐c, e). However, the solid obtained from 7 and two equiv. of cinnamaldehyde proved to be an imine (10g), which again formed in solution a similar triple tautomeric system analogously to the mutarotation of sugars. The structure of 11a and 10g was confirmed by X‐ray crystallography.

Original languageGerman
Pages (from-to)2065-2070
Number of pages6
JournalChemische Berichte
Volume124
Issue number9
DOIs
Publication statusPublished - Sep 1991

Keywords

  • 3H‐[1,2,4]‐Oxadiazolo[4,3‐c]pyrimidine, 5,6,7,8‐tetrahydro‐
  • Ring‐chain tautomerism

ASJC Scopus subject areas

  • Chemistry(all)

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