Thiazole constrained analogues of the thevinones: Synthesis and structure

Attila Sipos, Timea Skaliczki, Sándor Berényia, Sándor Antusa

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A simple synthesis of ring-constrained endoethenomorphinans possessing 2'-substituted thiazole ring 4-6 has been achieved by regio- and stereoselective Diels-Alder reaction of thiazolomorphinandienes 1-3 and methyl vinyl ketone in high yield (72, 64 and 87%, respectively). The structure of cycloaddition products was determined by high resolution mass spectrometry (HRMS), IR, 1D and 2D NMR techniques. Double-pulsed field gradient spin-echo-nOe and HMBC were found to be particularly powerful and indispensable tools in the exact structural elucidation of the presented new class of spatially constrained thevinones.

Original languageEnglish
Pages (from-to)801-807
Number of pages7
JournalMagnetic Resonance in Chemistry
Volume47
Issue number9
DOIs
Publication statusPublished - Sep 1 2009

Keywords

  • DFT study
  • NMR
  • NOe
  • Opioid activity
  • Thevinones

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

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