Synthesis and conformational behaviour of 2-phenylperhydropyrrolo[1,2-4][1,3,4]oxadiazine and 2-phenylperhydropyrido[1,2-d][1,3,4]oxadiazine; new heterocyclic ring systems

Ari Rosling, Ferenc Fülöp, Reijo Sillanpää, Jorma Mattinen

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Hydrazino alcohols, 1-amino-2-hydroxymethylpyrrolidine (1) and 1-amino-2-hydroxymethylpiperidine (2), were synthesized and subsequently ring closured with ethyl benzimidate to the title compounds (7) and (8), which have new ring systems. Variabletemperature 1H nmr measurements, supported by X-ray analysis, indicated that pyrrolo[1,2-d][1,3,4]oxadiazine (7) exists exclusively in a cis-fused conformation (in CDCl3 at room temperature), whereas pyrido[1,2-d][1,3,4]oxadiazine (8) adopts a trans-fused conformation.

Original languageEnglish
Pages (from-to)95-106
Number of pages12
JournalHeterocycles
Volume45
Issue number1
Publication statusPublished - Dec 1 1997

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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